The immediate reflex is usually to do something drastic. You think you need to rewrite your entire website, launch a massive marketing campaign, or start cold-pitching strangers on LinkedIn.

But business development at this level rarely requires a megaphone. It usually just requires a conversation.

If you are looking at an empty quarter and feeling the stress creep in, take a breath. You don’t need a complex strategy to get things moving again. You just need to tend to your ecosystem.

Here are five low-friction things you can do this week to wake up your pipeline.

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1. Build a Minimum Viable Pipeline

You cannot manage what you cannot see. If your current method for tracking potential clients is relying on your memory or flagging emails in your inbox, you are going to drop the ball.

You do not need an expensive CRM software subscription to fix this. You just need a single, centralized list. Open a blank spreadsheet right now. Add five columns: Name, Organization, Description of Opportunity, Last Contact Date, and Next Step.

Write down every active conversation you have going. Just getting it out of your head and onto a screen will instantly reduce your anxiety and show you exactly where you need to follow up.

2. Email three people you genuinely enjoyed working with

The best consulting leads do not come from cold pitches. They come from fertile ground—people who already know your work, trust your expertise, and actually like you.

Pick three former clients, colleagues, or partners who you loved collaborating with in the past. Send them a short email.

• Do not pitch them a service.

• Do not ask for a referral.

• Just say hello.

Ask how their current quarter is going. Commiserate about a challenge you both understand deeply. Congratulate them on a recent win. Reconnecting as a human being is the most powerful business development tool you have.

3. Kill a zombie lead

Look at that pipeline you just built. Is there someone on there who has been sitting in the “maybe” phase for three months? The prospect who keeps delaying the kickoff or ghosting your check-ins?

They are draining your mental energy. You are keeping them on the list because it feels like safety, but they are actually a weed taking up space in your garden.

Send the polite, final email: “It sounds like the timing isn’t quite right for this project. I’m going to close the file on this for now, but let’s reconnect when your team is ready.” Take them off your active list and reclaim that energy for viable prospects.

4. Send a resource with no strings attached

Think about one warm lead in your network who is currently tackling a specific problem. Now, find an article, a podcast episode, or a template that might help them solve it, and send it their way.

“Saw this and thought of the project you mentioned last month. Hope it’s helpful.”

This is the core of lead cultivation. It keeps you top-of-mind, it proves your expertise, and it demonstrates that you are invested in their success long before there is a contract on the table.

5. Schedule a 15-minute CEO block

Consistency beats intensity every time. Spending 15 minutes a week building your pipeline is vastly more effective than waiting until your current contract ends, panicking, and spending 10 hours on it when you’re already in scarcity mindset.

Open your calendar and block out 15 minutes for next Monday afternoon. Treat this block exactly like a meeting with a paying client. When that reminder goes off, open your spreadsheet, see who needs a follow-up, and send the email.

Keep It Simple (and Get Some Accountability)

You don’t need to be aggressive to be profitable. You just need to be organized and consistent.

If you want a framework to help you start conversations with prospective clients without feeling pushy, grab my pay-what-you-can Lead Cultivation Workbook to get your spreadsheet started.

But if you know yourself... and you know that the 15-minute “CEO block” is going to get deleted the second a client asks for something urgent, you don’t need another workbook. You need accountability.

On June 1, we are kicking off the Cultivated Pipeline, a 9-week sales accountability group for consultants. We are going to strip out the complicated funnels, build your minimum viable pipeline, and actually hold each other to the habit of regular, low-friction follow-up.

If you want to stop panicking about your pipeline and start building it sustainably alongside a community of peers, come join us.

Learn more and claim your spot here

I designed The Cultivated Pipeline to be that system. This isn’t just another course where you watch videos and hope for the best. This is a 9-week live accountability journey specifically for independent consultants in the international development and social impact space.

The Support System You’ve Been Missing

While my on-demand course, The Art of Lead Cultivation, provides the blueprint, this program is the trellis. It’s the structure you need to move from “aimless networking” into active business development alongside peers who truly get the nuances of this industry.

The 9-Week Journey

We move through three intentional phases to ensure you aren’t just “busy,” but actually building a pipeline:

• 🌱 Germination (Weeks 1–3): Mapping your network and identifying growth sectors.

• 🌿 Cultivation (Weeks 4–6): Turning discovery notes into market intelligence and testing your professional language.

• 🌸 The Bloom (Weeks 7–9): Troubleshooting sales in real-time to transition warm conversations into signed contracts.

Choose Your Level of Support

I’m offering two ways to join this June:

• The Accountability Group ($273): This is the community-powered path. You get 9 weeks of live 60-minute sessions, the full toolkit of worksheets, and ongoing peer support in the Bosscraft Network.

• The Lead Cultivation Upgrade ($1011): For those who want a deeper dive. This includes everything in the regular group, plus four private 1:1 coaching sessions with me to overhaul your specific proposals, rates, and outreach strategy.

Join Us This June

We meet on Mondays at 1:00 PM ET starting on June 1st. I keep the cohort intentionally small to ensure we can hold space for every participant’s specific hurdles.

Check out the full details & enroll here

When you are a solo practitioner, business development often feels like a chore that gets pushed to Friday afternoon, then Saturday morning, and then eventually off the calendar entirely. Why? Because doing it alone is exhausting. There is no water cooler to stand around and vent about a ghosted proposal, and there is no manager to help you prioritize which lead is worth your energy.

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The Motivation Trap

We often wait for “motivation” to strike before we reach out to a new lead or update our capability statements. But motivation is a fickle resource, especially when you’re already managing client deliverables. The truth is that consistency beats motivation every single time.

But how do you stay consistent when you’re the only one watching? This is where the “hustle” culture fails us. It tells us to work harder and stay up later, but it doesn’t give us the structure to work smarter.

Why Accountability Changes the Math

Accountability isn’t about having a “boss”; it’s about having a mirror. In a marketing context, accountability provides three things that solo work cannot:

• Normalization: Realizing that everyone—even the veterans—finds discovery calls intimidating makes them easier to do. When you hear a peer describe the same hurdle you’re facing, the shame of “not being good at sales” evaporates.

• External Deadlines: We are great at meeting client deadlines, but terrible at meeting our own. When you know you have to report your progress to a peer group on Monday, you’re much more likely to send that follow-up email on Friday.

• Real-Time Troubleshooting: Isolation turns small hurdles into brick walls. Accountability turns them into group problem-solving sessions. Instead of spinning your wheels on how to word a sensitive email, you get five perspectives in five minutes.

From Burnout to Bloom

Constant hustle is a recipe for burnout. Burnout kills your confidence, and more importantly, it kills your best ideas. By building a “trellis” of support—a structured rhythm of prospecting and peer review—you protect your energy for the missions that matter most.

In my recent reflections on the Wheel of Fortune, I talked about the unpredictable cycles of the last year—the anti-trans cultural shifts, the disruption of the federal workforce, and the sudden disappearance of career paths we thought were paved in stone. But there is a secondary cycle that happens in the quiet of your own office: the cycle of the sole motivator.

When you work for yourself, silence isn’t just a lack of noise. It’s an interrogation. Without the external mirrors of a boss or a team to reflect your value back to you, you’re forced to provide your own validation. And on the “sticky-messy” days, that validation feels like a lie.

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The Myth of the “Lone Wolf”

We’re told that success is a straight line powered by sheer willpower. But building alone makes everything harder because you are both the fuel and the engine. When the engine stalls—not because of laziness, but because of the sheer weight of global and personal upheaval—the Imposter is the first one at the door.

He whispers that the reason the course didn’t fill or the coaching package didn’t land isn’t because of a shifting market or a need for a pivot. He tells you that your previous wins were just “luck” and that this current silence is the “truth.” This is the core of imposter syndrome in a vacuum: without a performance review to ground you, you start to believe that you were never “that person” to begin with.

The Safety of Smallness

Lately, I’ve realized that my own self-limiting barriers often look like “productivity.” I’ve spent hours panic-applying to ‘real jobs’ or tweaking the backend of a website instead of doing the high-exposure work that actually matters.

It’s a defense mechanism. If we stay in the “weeds,” we don’t have to face the vulnerability of the big “Yes.” We tell ourselves we need one more certification or a perfectly color-coded spreadsheet before we’re “ready.” We protect ourselves with a Strategic “No” that is actually just a fear-based ‘not yet.’ If we don’t put the work out there, we can’t be rejected—but we also can’t be found.

Pruning the Mess

The messiness doesn’t go away by working harder. It goes away by pruning.

In this cycle of my own “Bosscraft,” I’m learning to stop fighting the external forces and start leaning into the natural rhythm of things. The “sticky” feelings are often just a signal that I’m trying to sustain something that isn’t sustainable. They are symptoms of a misstep that stalls your practice—trying to do everything for everyone while ignoring your own intuition.

We don’t need to be “fixed”; we need to be focused. We need to decide based on the math and the joy, not the 3:00 AM anxiety.

The Wheel is always turning. The trick to being your own boss isn’t staying at the top of the wheel—it’s learning how to keep your hands on the controls while it spins.

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On the Bosscraft Podcast and in the Bosscraft Community, we talk about building a practice that lasts. Usually, the Four of Wands is the “homecoming” card—the party, the launch success, the solid foundation. But what happens when that energy is flipped? Today, we’re looking at what it means when the structure feels shaky or the win doesn’t feel like the win you were aiming for. Are you building on solid ground, or is the internal “home” in need of repair?

The Card: Four of Wands (Reversed)

Take a moment to look at the card. Traditionally, it shows four upright staves garlanded with flowers, a symbol of harmony and peace. When reversed, those staves can feel like they are falling over, or perhaps the celebration is happening behind closed doors where no one can see it. What do you see? Do you see a party that was cancelled, or an intimate moment of joy that doesn’t need an audience?

I use the Vindur Tarot deck, developed by Leah Pantéa, which is now out of print, but I recommend learning a deck that strongly reflects the Rider-Waite imagery.

The anatomy of the card:

• The Suit (Wands): In tarot, Wands represent the element of fire. They govern inspiration, ambition, spiritual growth, and the “spark” of your business.

• The Number (Fours): Fours represent structure, foundations, and stability. It is the “square” that holds things together.

• The Reversal: When reversed, the Four of Wands suggests a period of internalized transition. The stability isn’t missing; it’s just being rearranged. It often points to tension in the “home” (your core business or team) or a feeling that you can’t quite relax yet.

In the reversed position, the Four of Wands represents a lack of harmony or a delayed milestone. It’s that feeling when you hit a goal, but you’re too exhausted to celebrate. Or maybe “success” doesn’t look quite like what you imagined it would. This card reminds us that external success is hollow if the internal foundation is cracked. However, it is also a card of private victory. It calls us to find happiness within our own process, rather than waiting for external validation or a “perfect” ribbon-cutting ceremony.

For mission-driven folks, the energy of the reversed Four of Wands calls for a different kind of strength. It shows up when:

• You’ve achieved the “success” people expect, but it feels disconnected from your actual mission, leaving you feeling unsettled rather than proud.

• You realize the “back end” of your practice—the systems, the boundaries, or the culture—is wobbling under the weight of your recent growth.

• You are doing the hard, invisible work of restructuring your life or business, and you have to learn to be your own cheerleader before the world sees the result.

• You’re dealing with friction in your closest circles (partners, key team members, or clients) that is draining the energy you need for your creative work.

The Bosscraft Take: Embodying the lesson of the Four of Wands (reversed) isn’t about admitting defeat—it’s about finding your foundations. This card is an invitation to stop looking for the next big win and start looking at the health of your home base. When you are aligned with this energy, you recognize that a delayed celebration is often a blessing in disguise—it gives you time to make sure the foundation can actually hold the weight of your dreams. It’s time to stop performing "stability" and start actually building it.

The Conversation

Become a paid subscriber or Bosscraft Consultant community member to join in the discussion and access our private chat.

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This week’s prompt: The Four of Wands (reversed) asks us to look at the cracks in our foundation. What is one area of your practice or life where things feel “unsteady” right now, and what is one small internal shift you can make to feel more at home in your work?

I’ll be in the comments sharing a recent “win” that actually felt like a lot of work, and how I’m trying to find the joy in the messy middle.

1. Putting the Cart Before the Horse

It is incredibly tempting to spend your first week picking brand colors, ordering embossed business cards, or agonizing over whether to file as an LLC or an S-Corp. While these tasks feel like work, they are often "procrastivity" traps—high-effort activities that protect you from the vulnerability of actual selling. You should prioritize the "horse," which is a signed contract for paid labor. You don’t actually have a business until someone agrees to pay you for your expertise; until then, you have an expensive hobby with a beautiful logo. If you are struggling to move past the administrative fog, focus your initial energy on securing that first "Yes," and let the polished structure follow the revenue.

2. Becoming a “Secret Agent” Consultant

There is a common hesitation among new consultants to broadcast their transition, often stemming from a fear of looking “unemployed” or “between jobs.” However, you cannot get referrals for work that no one knows you do. Staying quiet is the fastest way to stall your pipeline. No one is going to hire you if they don’t know you are consulting!

You must be vocal about your new venture by updating your LinkedIn, sending personal notes to your network, and being specific about the problems you solve. It feels scary because it is, but that doesn’t mean that you don’t do it! Remember that building alone makes everything harder; your community is your most effective lead generator, but only if they know you’re open for business.

3. Assuming a 40-Hour Billable Week

In a traditional job, you are generally paid for forty hours of "availability," regardless of how many of those hours are spent in a deep flow state. New freelancers often set their hourly rates by dividing their desired salary by 2,080 hours, assuming they will bill a full week every week. This is a fast track to burnout or financial ruin because it ignores the reality of non-billable overhead. And, you know, things like making yourself lunch, taking vacations, getting sick… all those things that we don’t always think about on first glance! Instead, you must calculate your rates based on a realistic "utilization rate." My starting point for most freelancers? Assume about 20 to 25 billable hours per week.

4. Not Tracking All Your Time

Most new consultants only track the hours they plan to put on an invoice, which creates a massive blind spot in their business model. By ignoring the time spent on "quick" client emails, project research, and administrative tasks, you lose sight of your true hourly realization. You should commit to tracking every minute of your workday for at least the first three months. You will likely find that a project you estimated at ten hours actually consumes eighteen. This data is the only way to ensure your decisions are based on numbers rather than optimistic guesses, allowing you to price more accurately in the future.

Tracking all of your time means that you know how much of your week is working hours and how much of those working hours can reasonably be considered available for billable work. This helps you hone your “utilization rate” from my estimated 20 to 25 hours to what’s realistic to you.

5. Ignoring the “Sustainability Math”

It is surprisingly easy to leap into consulting without fully investigating the "floor"—the actual dollar amount required to sustain your life and business. Many freelancers focus on the top-line revenue of a contract without accounting for self-employment taxes, health insurance, and a necessary rainy-day fund. To avoid a mid-year crisis, you must run the numbers early and often. Understanding your scarcity vs. bounty mindset begins with the cold, hard reality of what it costs to keep your practice running comfortably.

To get the math right based on the actual hours you plan to work and what you need to keep your work sustainable, I recommend using the Sustainable Rate Setting Workbook, which helps you account for all of the “business of the business”—the admin, marketing, and creative thinking time that keeps your practice alive.

6. Using “Enterprise” Systems for a “Solo” Reality

If you spent years in a large organization, you likely grew accustomed to robust tools like Salesforce or complex project management suites. It is a mistake to think you need that same infrastructure to succeed as a solo consultant. As noted in You Don't Need Salesforce to Succeed, complex systems often become a burden rather than a benefit for a team of one. After all, the system that was built to keep 100+ people across 10+ country programs in constant contact and optimize coordination is not built to keep you organized. Different goals need different tools!

Your goal should be to keep your "tech stack" as lean as possible. Start with a simple spreadsheet or a basic tool that requires minimal maintenance (and cost), ensuring that you aren't spending your precious unbilled hours or financial resources acting as your own IT department.

7. Cold Emailing Instead of Cultivating Relationships

Blasting out cold pitches to strangers can feel productive because it results in a high volume of "outreach," but it rarely builds the high-level trust required for consulting. Consulting is a relationship-based industry where the "product" is your brain and your reputation. Rather than shouting into the void of an inbox, pivot your energy toward relationship-building. Reconnect with former colleagues and offer genuine value without an immediate ask. If you aren't sure how to start those conversations, the Lead Cultivation Workbook offers a low-pressure, curiosity-led framework to help you build a pipeline without the "salesy" hustle.

Pro-Tip: If you're feeling overwhelmed by these shifts, remember that trimming back to make space is part of the process. You're not just a worker now; you're the boss. Start acting like one!

Start giving yourself the strategic oversight that a CEO would provide—and if you need a community of peers to gut-check your decisions, come join us in the Bosscraft Consultant Network.

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On the Bosscraft Podcast and in the Bosscraft Community, we often discuss the reality of sustainability in your consulting practice, including finances. But today, we’re looking at the energy behind it. Success isn’t just about the “up” moments; it’s about how we navigate the “down” ones. Are you leading with a scarcity mindset, or can you see the light through the window?

The Card: Five of Pentacles

Take a moment to look at the card. Traditionally, it depicts two figures walking through the snow, past a glowin stained-glass window. In my deck, the stained glass window is shattered, breaking the beautiful facade. What do you see? Do you see the struggle of the strom or the proximity to warmth? Is there help waiting, if you looked up to see it?

I use the Vindur Tarot deck, developed by Leah Pantéa, which is now out of print, but I recommend learning a deck that strongly reflects the Rider-Waite imagery.

The anatomy of the card:

• The Suit (Pentacles): In tarot, Pentacles represent the element of earth. they govern the physical world: finances, health, career, and material resources.

• The Number (Fives): Upright, Fives often represent a moment of instability, conflict, or change. It’s a transition point in the cycle where things feel off balance. Reversed they may be more about an internal change or sticking point.

In the upright position, the Five of Pentacles represents a period of material or financial winter. It’s that moment in which resources feel thin or you feel excluded from a warm inner circle, of sorts. Maybe you are equating the stability and warmth that material resource provide with happiness and fulfillment. However, it is also a card of resilience. It reminds us that help is often available, but we are frequently too focused on our own struggle to ask for it. It may also remind us of what we have, and call us to use our own material wealth to support others who need it.

For mission-driven folks, the energy of the Five of Pentacles calls for a different kind of strength. It shows up when:

• You find yourself in a “losing” season—a launch didn’t go as planned or a key partner walked away—and you realize this is the moment to see what core truths remain once the external fluff is stripped away.

• You catch yourself falling into the “scarcity trap,” where your decisions start being driven by a fear of “not enough” rather than the deep, guiding mission that started your practice.

• You confront the “lone wolf” fallacy, realizing that struggling in silence because you think a leader “should” have it all figured out is actually the only thing keeping you out in the cold.

• You stop staring at the closed door and finally notice the “stained glass”—the community support, personal health, and dormant wisdom that have been right next to you all along.

• You trade the exhaustion of “powering through” for the grace of radical honesty, understanding that asking for help isn’t a sign of failure, but a strategic move toward sustainability.

The Bosscraft Take: Embodying the lesson of the Five of Pentacles isn’t about wallowing in a hard season—it’s about having the humility to look up. This card is an invitation to stop pretending you are an island and to start leading from a place of communal resourcefulness. When you are aligned with this energy, you don’t just survive a downturn; you use it to build a more honest, resilient foundation and look for opportunities to support others. It’s time to stop trying to be the hero of a tragedy and remember that the light in the window is meant for you, too.

The Conversation

Become a paid subscriber or Bosscraft Consultant community member to join in the discussion and access our private chat.

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This week’s prompt: The Five of Pentacles asks us to look up from our struggle and notice the support available to us. What is one area where you’ve been “walking in the cold” alone, and what is the “warm window” (a resource or person) you’re ready to reach out to?

I’ll be in the comments sharing a recent moment where I had to trade my “I’ve got this” armor for a little bit of community warmth.

But have you ever signed a client or job opportunity that checked every “good decision” box on paper, only to feel a pit in your stomach the moment you took a moment alone?

That’s your internal system flagging a qualitative data point your spreadsheet missed.

The reality is that we don’t exist solely as sets of figures. Designing and running your work life as if you are a calculator is a sure path to burnout. To build a sustainable freelance consulting practice, you don’t need to choose between numbers and feelings.

You need to learn how to let them talk to each other.

The Role of Numbers: Your Guardrails

Numbers can provide the objective truth of your business (but not the whole truth). They represent the “what.” Without them, you aren’t running a business; you’re running a hoppy that is fueled by hope. If you want your practice—or career pivot—to be sustainable it has to pay the bills.

Numbers help you strip away the stories we all tell ourselves about success. A few cases in point, based on my own recent experience:

• I felt like I incredibly busy, but my time tracker pointed out that I was actually really underbilling my time and had space to take on another client.

• I had a sinking feeling that one service area was dying out, but my numbers helped me see that what I was experiencing was a typical seasonal lull that will likely pick up.

• I felt like no one was reaching out, but my pipeline showed that I was managing more possible opportunities than before.

In my NEW planning toolkit, I emphasize tracking a few simple metrics like:

• Net Profit: What are you actually bringing in, after expenses?

• Lead Source: Where are your best-paying, least-stressful clients coming from, and how many hooks do you actually have in the water?

• Capacity: Exactly how many hours do you have left before the quality of your output starts to tank?

Numbers keep you solvent. They ensure that the lights stay on.

The Role of Feelings: Your Compass

If data is the “what,” feelings are the “why.” Feelings pick up on the nuances that a CRM can’t see—like the tone of a client’s email or the way your energy levels plummet when you see a specific meeting on your calendar.

In freelancing, your “gut” is actually just a very fast processor of qualitative data:

• The Sunday Scaries: If you feel dread on Sunday night, the numbers don’t matter. A “profitable” project that makes you miserable is a failed project.

• The Friction Point: If a simple onboarding process feels like pulling teeth, the “data” of the contract doesn’t matter—the relationship is already over-leveraged on effort.

• Alignment: Does this work actually make you feel like the “Boss” you set out to be, or are you just building a new job for yourself with a worse boss?

Feelings keep you sane. They ensure that you actually enjoy the life your numbers are paying for.

The Sweet Spot: The Integration Matrix

To find the right balance, I like to look at my work as though it’s sitting at the intersection of the “data” axis and the “feelings” axis.

There is a spectrum between projects that come with positive data (good money, good hours, important clients) and those that demonstrate negative data (low rates, ongoing problems, other bummers), just as there is a spectrum between projects that come with positive feelings (great teams, fun work, fullfilling outcomes) and those with negative feelings (miserable teams, unfullfilling work, actively doing things you hate).

When you’re sitting in each of these quadrants on the spectrum, you get a general outcome:

• Negative feelings + negative data = the danger zone. Low pay, high stress, basically a constant bummer (and a client you need to fire asap).

• Negiatve feelings + positive data = the golden handcuffs. High pay or prestige factors, but you had what you’re doing or who you’re doing it for. A challenge to unload, but a definite road to burnout if you stay on it too long.

• Positive feelings + negative data = the passion project. Not a bad thing inherently, but insufficient pay or bad processes can lead to resentment, if you don’t accept this for what it is.

• Positive feelings + positive data = the flow state. Getting paid what you’re worth to do work you love doing with folks you love doing it for? The dream. Also, my definition of what makes an “ideal client.”

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The Verdict

The most successful consultants I know aren’t just math whizzes or “vibes” people—they are bilingual. They speak the language of profit and the language of intuition.

If the numbers say “Yes” but your gut says “No,” listen to your gut. It’s usually seeing a red flag that hasn’t hit the balance sheet yet.

But if your gut says “Yes” and the numbers say “No,” listen to the numbers. They are trying to save you from a “passionate” path toward bankruptcy.

The goal isn’t to be one or the other. The goal is to be both.

Your planning efforts should reflect that balance between the numbers and the feelings. That’s why I’m so happy with the newly revamped Boss Insights Reflection and Planning Toolkit. It’s my happy medium with both sides speaking volumes.

Grab Your Copy Now

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You spent seven days trying to disconnect. You set the auto-responder. You maybe even left your laptop at home. You feel, for a brief moment, like a human being again.

Then you open your inbox.

Within 45 minutes, that hard-won peace is gone. The adrenaline spikes, the dread returns, and you realize you aren’t "refreshed." You’re just back in the grinder, only now you’re 500 emails behind.

We need to stop treating vacations as the cure for burnout.

The Battery Myth

We tend to treat ourselves like rechargeable batteries. We think that if we run ourselves down to 0%, all we need is a “plug”—a long weekend, a spa day, or a trip to the coast—to get back to 100%.

But burnout isn’t just an empty battery. It’s a broken circuit.

If you take a fully charged battery and plug it into a short-circuited machine, it will drain again in seconds. The problem isn’t that you need more time on a beach; the problem is that you are returning to a workflow designed to deplete you.

Pause vs. Fix

A vacation is a pause button. It stops the noise for a moment, but it fixes absolutely nothing about the source of that noise.

• It doesn’t fix the client who texts you at all hours.

• It doesn’t fix the fact that you are undercharging and overworking to make ends meet.

• It doesn’t fix the lack of delegation that makes you the bottleneck for every decision.

You cannot rest your way out of a broken system.

If your work requires you to run at a sprint just to stay in place, no amount of PTO will save you. You don’t need an escape; you need a remodel.

Recovery Happens on Tuesday

True sustainability isn’t about the two weeks a year you aren’t working. It is about the 50 weeks you are. The cure for burnout is found in the boring, unglamorous structure of your average Tuesday:

• It’s in the boundaries you hold when a client asks for “one more thing.”

• It’s in the systems that allow work to flow without your constant intervention.

• It’s in the pricing model that allows you to work 30 hours instead of 60.

This is the difference between “coping” with your business and actually leading it.

Build a Life You Don’t Need to Escape

If you are tired of the cycle—sprint, crash, vacation, repeat—it is time to look at the machinery, not the calendar.

I don’t help my clients plan their next trip. I help them redesign their workday so they don’t collapse the moment they get home. We look at the roots, fix the leaks, and build a container strong enough to hold your ambition without crushing you.

Join Us This Friday

If you’re ready to stop recovering and start rebuilding the “circuitry” of your business, join me for our upcoming session:

Beyond the Burnout

Date: Friday, April 3rd

Time: 10:00 AM ET

Register for Beyond the Burnout

This event is free for Bosscraft community members and an affordable low price for all others. Please don’t allow financial barriers to limit your access and send us an email.

Let’s stop talking about vacations and start talking about how to make your “average Tuesday” actually sustainable.

📍 In case you missed it, catch up on the last bulletin.

📍 If you’d like to request that an opportunity be featured in the next bulletin, email bulletin@bossinsights.org with the details.

📍 Selected events and job opportunities are available for all. To access freelance consulting assignment listings, join us with a paid subscription.

Become a Paid Member

Paid members receive access to the Bosscraft Podcast, member-only events, curated resources, and face-time with Boss Insights founder, Whitney Kippes.

We know that growing a cultivated career requires the right conditions. Whether you are looking to plant seeds with new connections or find the right soil for your unique skills, we’ve curated this list to help you thrive in the current season.

🌻 Cross-Pollinating

Connect with peers, attend workshops, and learn at events with your community.

• Bridging Cultures, Building Influence is a session hosted by our friend Tiffany Green of Emergent Inquiry Consulting to discuss how organizations can build trust and credibility within their team while working across cultures.

  • 📅 10am ET on 30 March

  • 🎟️ Free registration here.

• Beyond the Burnout, a discussion of how burnout impacts work, motivation, and enthusiasm, facilitated by Boss Insights founder Whitney Kippes. to spotlight grassroots humanitarians. FREE registration here.

  • 📅 10am ET on 31 March

  • 🎟️ Free registration here.

• Community Building for Your Social Impact Career is a session on reframing networking as community building (kudos!), based on Erin Mogel’s work as a career coach in the social impact space.

  • 📅 1pm ET on 31 March

  • 🎟️ Free registration here.

• The Future is Cooperative - Meet Some of the Young Women Leading It is a session hosted by NCBA CLUA to discuss the future of the cooperative movement and profile some incredible folks leading the charge.

  • 📅 2pm ET on 31 March

  • 🎟️ Free registration here.

• How to Be the Boss You Wish You’d Had is a 90 minute workshop from Abby Alexanian for nonprofit and public sector team leaders will help you meet this critical moment by being the boss your team needs.

  • 📅 12:30pm ET on 2 April

  • 🎟️ $99 to register here.

• Bosscraft Peer Support Check-in, a monthly space to check in, share what’s working (and what’s not), and get encouragement from others walking a similar path.

  • 📅 9:30am ET on 7 April

  • 🎟️ Exclusive to active Bosscraft members.

• Show Me Your CRM, a Bosscraft workshop free to community members and paid for the public, in which we’re going to have an open discussion about how to track client relationships and tasks in your freelance work.

  • 📅 11am ET on 15 April

  • 🎟️ Free for Bosscraft members, all others register here

• Bosscraft Co-working Session, a body-doubling call designed for us to show up together, create accountability, and make progress side by side.

  • 📅 10:30am ET on 23 April

  • 🎟️ Exclusive to active Bosscraft members.

• Client Prospect Research, a Bosscraft workshop free to community members and paid for the public, in which we’ll talk about a simple approach to lead cultivation, based in the core need to talk to prospective clients.

  • 📅 11am ET on 12 May

  • 🎟️ Free for Bosscraft members, all others register here

🌿 Putting Down Roots

Discover permanent positions at social impact organizations doing work worth doing.

• ChildFund International is recruiting for multiple resource mobilization positions (Advisor II and Advisor Sr.), which can apparently be based in any several different ChildFund countries.

  • 💰 Pay is based in non-U.S. currencies.

• Counterpart International is recruiting for a Senior Director of Philanthropic Partnerships as well as a few other roles, including some in East Africa.

  • 💰 $140,000-180,000

• Crisis Text Line is looking for a Senior Director of Corporate Partnerships.

  • 💰 $125,000-150,000

• Food for the Hungry is hiring a Senior Pricing Manager to join their business development team, to be based in Phoenix, AZ or Washington, DC.

  • 💰 Compensation information not available.

• Fresh Energy, a Minnesota-based non-profit, is looking for Director of Major Gifts to join their development team.

  • 💰 $85,000-100,000

• GiveDirectly is looking for a Senior Research Manager to explore cash transfers at a regional or national scale.

  • 💰 $109,200 + 10% bonus

• Global Refuge is looking for a Senior Program Officer for Employment Services to support refugee resettlement programs.

  • 💰 $74,900

• International Rescue Committee is looking for a London-based, English- and French-speaking Program & Award Officer to support programs in Africa.

  • 💰 £44,500 - £47,000

• KABOOM! is looking for a Director of Development which focuses on corporate, foundation, and individual funders.

  • 💰 $139,000-161,000

• MCD Global Health is hiring a two Senior Manager Finance positions, as well as a variety of other Maine-based positions.

  • 💰 $97,000-110,000

• Mercy Corps is hiring a Senior Advisor Major Gifts with flexible location (ideally in the Midwest or on the East Coast.

  • 💰 $86,000-100,000

• Mercy Corps is also hiring a Program Director for their newest program in Sudan, EMPOWER. Looks like they may have been flooded with applications, so look to personal connections!

  • 💰 Compensation information not available.

• MSH is hiring a Business Development Specialist—which reads like an early career position—to be based in Arlington, VA.

  • 💰 $60,000-85,000

• National Geographic Society is looking for a Senior Director, Philanthropic Foundations which sounds like such fun.

  • 💰 $166,000-175,000

• The Hatcher Group is hiring a Proposal Specialist to support proposal cordination and other business development functions, based in Bethesda, MD.

  • 💰 $85,000-105,000

• Village Enterprise is hiring an Institutional Partnerships Manager to be based in East Africa (Nairobi, Kampala, Kigali, or Addis Ababa).

  • 💰 Compensation information not available.

• VEIC (clean energy) is recruiting for a Proposal Manager and Senior Proposal Manager.

  • 💰 $80,000-90,000 and $100,000-110,000

• WAMU—that’s the DMV public radio folks—is hiring a Major Gifts Officer to support their development office.

  • 💰 $90,000-110,000

• WILD Foundation is hiring a Conservation Networks & Facilitation Manager to support expanding international conservation efforts.

  • 💰 $70,000-80,000

• World Wildlife Foundation is hiring a Senior Director for International Fianancial Institutions to coordinate a global strategy on engaging the IFIs.

  • 💰 $200,000

Missed last week? Catch up here:

🔒 Ready to focus your energy on the opportunities that actually bear fruit?

Paid members unlock The Trellis—our selection of short-term contracts, technical assistance roles, and fractional consulting gigs. Stop scattering seeds in the wind and start applying for roles that fit your specific craft. Join the to gather this week’s harvest.

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You start feeling the itch to grow. You want to launch the new offer, chase the big contract, or start networking with a whole new tier of potential clients or collaborators. You are ready to plant seeds.

But before you go out and buy a bag of expensive fertilizer, look at your garden.

Is it ready? Or is it overgrown with the weeds of last year’s “maybe” projects, unfinished admin, and clutter?

The biggest mistake ambitious consultants make is trying to plant new ideas into a chaotic system.

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Growth Amplifies Chaos

If your current operations are messy, adding more clients won’t fix the problem. It will just scale the mess.

• If your onboarding process is a manual scramble, adding three new clients will break you.

• If your inbox is a disaster zone, adding more leads will just mean more dropped balls.

• If you are already over-committed to low-value work, adding high-value work will just lead to burnout.

You cannot build a skyscraper on a cracked foundation. And you cannot grow a sustainable business if you don’t take the time to prepare the soil.

The Operational Reset

Before you start your spring offensive, you need to “clear the decks.”

This isn’t glamorous work. It doesn’t look like “hustle” on Instagram. It looks like boring, quiet maintenance. But it is the difference between a business that blooms and a business that gets choked out.

1. Close the Zombie Loops Look at your to-do list. How many items have been on there for three months? Either do them today, or delete them. If it hasn’t happened by now, it’s not a priority. It’s just guilt. Archive it and move on.

2. Clean Your Digital House File the contracts. Send the final invoices. Archive the Slack channels for finished projects. Clear the visual clutter so your brain has space to see the new opportunities.

3. Prune the Pipeline This is the hardest one. You likely have “opportunities” hanging around that are stagnant. The client who ghosted you three weeks ago. The proposal that is “on hold.” The friend you meant to follow-up with.

We keep these alive because they feel like safety. But they are actually weeds. They are taking up mental nutrients that should be going to your active, healthy prospects.

Decide What Gets Watered

You need to be ruthless about what you allow to take up space in your garden this season. Pull the weeds—the dead leads, the misaligned requests, the energy drains.

Once the soil is clear, you need a way to intentionally water the seeds that actually matter.

How do you keep track of your active, healthy relationships without letting them slip through the cracks or turning into a pushy salesperson? You don’t need a complicated software system to do it. You just need a simple, repeatable routine.

Use this Lead Cultivation Workbook to organize your thinking on what prospects you want to bring in, hone your messaging, and build a low-pressure system for nurturing your network.

Download the Workbook

Prepare the soil now, so when you do plant those seeds this season, they actually have the room—and the attention—to grow.

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On the Bosscraft Podcast and in the Bosscraft Community, we often discuss the mechanics of business. But today, we’re looking at the energy behind it. Success isn’t just about the “what”; it’s about the “how.” Are you leading with fear, or are you leading with the creative fire of a visionary?

The Card: King of Wands

Take a moment to look at the King. He sits on his throne, usually holding a flowering staff. What do you see? Is he restless? Is he commanding? Does he look like someone you’d follow into a new venture?

I use the Vindur Tarot deck, developed by Leah Pantéa, which is now out of print, but I recommend learning a deck that strongly reflects the Rider-Waite imagery.

The anatomy of the card:

• The Suit (Wands): In tarot, Wands represent the element of fire. They govern inspiration, spiritual drive, ambition, and the “spark” of a new idea.

• The Face Card (King): Kings represent mastery in tarot. This is someone who has moved past learning and is now directing energy outward to influence the world. Unlike the Queen, who focused on internal mastery, the King is externally focused.

In the upright position, the King of Wands represents the ultimate visionary—the person who can see the big picture and has the fire to execute it. When reversed (or when we are out of alignment with this energy), it suggests that while the "fire" is there, it’s either burning too hot (leading to burnout and aggression) or it’s being stifled by self-doubt.

For mission-driven folks, the King of Wands is giving serious leadership goals.His upright power shows up when:

• You lean into your “boldest” ideas because you realize that being “too much” is exactly what your industry needs to evolve.

• You transition from “manager” to “visionary,” inspiring your team not just through tasks, but by inviting them to help fuel a fire they actually believe in.

• You trust your intuition as the blueprint. You understand that while others need a map, you are the map—you have the confidence to pivot and pave the way as you go.

• You replace “busy-ness” with intentionality. Instead of putting out small fires, you are the one holding the torch, leading your team clearly toward a long-term, high-impact destination.

• You own your mastery without apology. You’ve traded imposter syndrome for a deep, grounded recognition of your track record and your unique right to lead.

The Bosscraft Take: Embodying the King of Wands isn’t about being the loudest person in the room—it’s about having the most stable fire. This card is an invitation to stop looking for external validation and to start leading from your own core vision. When you are aligned with this energy, you don’t just build a business; you build a legacy. It’s time to stop asking for a seat at the table and remember that you’re the one who built the table in the first place.

The Conversation

Become a paid subscriber or Bosscraft Consultant community member to join in the discussion and access our private chat.

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This week’s prompt: The King of Wands asks us to step into our power without apology. What is one bold, visionary move you’ve been sitting on that you are ready to claim as the “King” of your domain?

I’ll be in the comments sharing the specific area where I am currently stepping out of the shadows and fully owning my role as a leader.

As USAID was being upended and my previous consulting firm, Bid Boss, was shuttering its doors for unrelated reasons, I was at a crossroads. I knew I wasn’t done with the sector or the community of freelancers we’d brought together on our roster.

I built the Bosscraft Consultant Community because I needed a life raft. I knew I was launching something new in the middle of a crisis, so I kind of assumed the raft was bound for disaster—or at the very least short lived.

Today, we’re celebrating one year of being each other’s “virtual coworkers.”

We’ve survived the shifting tides of the global development sector by leaning on each other for gut-checks, accountability, and the kind of “is it just me?” conversations that I’ve always found with other bosses.

As we move into year two, I want to make sure everyone—from our original Bid Boss Coven members to our newest free subscribers here on Substack—knows exactly how to get the support they need.

1. The Boss Insights Free Subscription

For anyone who is “just lurking.”

If you aren’t up for the subscription cost but want to stay in the loop, stay right here. You’ll get my public reflections on building a career that fits your life and the occassional field guide to keep you aligned.

• Cost: $0 (just your email address)

2. The Boss Insights Paid Edition

For freelancers who need the “what” and the “where.”

This is the “data” layer of your freelance consulting practice. You get the biweekly Bulletin of curated job leads and opportunities and full episodes of the Bosscraft podcast delivered right to your inbox, plus a whole suite of tools in our Curated Consultant Toolkit ($150+ value).

• What it is: A high-value newsletter, podcast, and resource archive.

• Cost: $11/month.

Subscribe now

3. The Bosscraft Consultant Community

This is for those who are tired of the freelance “vacuum” and want real-time peer support.

As a Bosscraft Community member, you get everything in the Boss Insights paid subscription PLUS:

• Monthly ‘Gut-Check’ Sessions: Live Google Meet calls for instant feedback on your toughest client scenarios or pricing.

• Accountability Blocks: Virtual co-working dates to help you power through with a little chit-chat to keep you motivated.

• Private Community Forum: A forum-style space to ask “Is it just me?” at 2:00 PM on a Tuesday (or if you really need a specific question answered).

• The Full Implementation Toolkit: Our deepest library of templates and workshop recordings.

The best part? If you are in the Bosscraft Community, your paid subscription to Boss Insights is included. There is no need to join both.

Join the Bosscraft Community

Why am I telling you this?

1. For current Bosscraft members: Nothing changes for you! You’re already getting the full experience.

2. For free subscribers: If you’ve been thinking, “I wish I had someone to look over this bid with me,” or “I need a coworker today,” the Community is officially open for a few more of you to join us.

I’m so proud of the community we’re building here. Whether you’re here for the biweekly podcast or the daily “gut-checks,” thank you for being part of my evolving coven.

To being our own best bosses,

Whitney

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If a conversation wasn’t logged in Salesforce, it didn’t happen. The uphill battle to get everyone to use the common system was constant priority number one. Sharing information across the organization was everything. And, if you were lucky enough to be on a new business development or fundraising team, it brought you dashboards, lead scoring, and weekly pipeline review meetings. The machine was massive, and it was required to keep a 500-person organization dispersed around the globe moving in the same direction.

So, when you stepped out on your own, you naturally assumed you needed to build the same.

You signed up for a robust CRM, with a price tag that felt “worth it.” You spent three days building out color-coded pipeline stages, organizing your contacts, and crafting tags aligned to your service areas. You convinced yourself that doing this meant you were running a “real” business.

But now? You never log into it. It feels heavy. And honestly, you feel a little guilty every time you look at the subscription fee on your credit card statement.

It is time to let yourself off the hook.

Subscribe now

The Corporate Hangover

We often over-engineer our solo businesses because complexity feels productive. We think a complicated system makes us legitimate.

But for independent consultants, complex marketing plans and pipelines are usually a massive distraction. You are not a volume-based business. You aren’t trying to sell a $50 widget to 10,000 people. You likely only need five to ten solid contracts a year to hit your revenue goals.

At this level, you are selling trust, not stuff. And you cannot automate genuine connection with other human beings.

If you are spending more time managing the software than you are actually talking to human beings, you haven’t built an efficient back office. You have built a wonderfully distracting cage.

Permission to Stay in Your Comfort Zone

Because of this corporate hangover, we often assume that “doing BD” or “doing capture” requires adopting the highly coordinated, high-volume systems that once worked.

Or, we go down the path of the LinkedIn guru, who promises a six-figure salary if only you follow these “five easy steps.” Automated social posts and sales emails do not form real relationships. (I’ve been guilty of that one myself)

It’s also not about building the CV or website that will convince an AI bot that you’re perfect for the assignment.

The most effective pipeline for any freelance consultant is always the one that feels the most comfortable and natural to that specific individual. When your business is selling your skills and your capabilities, your marketing and lead cultivation efforts need to sound and behave like you.

Lead cultivation for freelancers at this level is simply relationship building.

• It is checking in on a former colleague when you see their organization in the news.

• It is sending a highly relevant article to a past client with a brief note.

• It is a 20-minute virtual coffee chat with a potential collaborator you admire.

• It is building friendships with fellow freelancers.

You are absolutely allowed to keep your lead cultivation process within your comfort zone. You don’t need to do cold outreach to strangers if your warm network is already full of strong relationships with incredible people. You just need a way to remember to actually talk to them.

Simple Wins Every Time

What does a functional, lightweight marketing and lead cultivaiton system look like for an independent consultant?

It only needs to answer four questions:

1. Who are the clients I want to work with most?

2. What specific problem can I solve for them?

3. When did we last connect?

4. When is my next touchpoint?

When you are the only person who needs to know what your last touchpoint with someone was, you don’t need a sexy sophisticated CRM. An organized folder of meeting notes is a valid CRM. A spreadsheet of potential clients is a perfectly valid CRM. A simple list in your notebook is a valid CRM.

If it keeps you in conversation with actual humans without creating unnecessary friction or fear, it is the right system for you.

Stop Managing Software. Start Cultivating Leads.

If the thought of opening your current sales tracker makes you want to hide under your desk, the problem isn’t your work ethic. The problem is the system you think you are supposed to use.

You don’t need a corporate tech stack to have a great conversation.

I built the Lead Cultivation Workbook specifically for freelance consultants who are ready to ditch the complexity and the bro-marketing tactics. It is a name-your-own-price tool designed to help you track your relationships, organize your follow-ups, and keep your pipeline moving naturally.

📍 In case you missed it, catch up on the last bulletin.

📍 If you’d like to request that an opportunity be featured in the next bulletin, email bulletin@bossinsights.org with the details.

📍 Selected events and job opportunities are available for all. To access freelance consulting assignment listings, join us with a paid subscription.

Become a Paid Member

Paid members receive access to the Bosscraft Podcast, member-only events, curated resources, and face-time with Boss Insights founder, Whitney Kippes.

We know that growing a cultivated career requires the right conditions. Whether you are looking to plant seeds with new connections or find the right soil for your unique skills, we’ve curated this list to help you thrive in the current season.

🌻 Cross-Pollinating

Connect with peers, attend workshops, and learn at events with your community.

• Devex Career Briefing: How to create a portfolio career playbook for long-term consulting stability, a practical framework from Kelsi Kriitmaa for defining clarity and positioning, offer and income design, visibility and pipeline building, and long-term portfolio architecture.

  • 📅 9am ET on 16 March

  • 🎟️ Pay to register as part of a Devex career’s membership here.

• Bosscraft Co-working Session, a body-doubling call designed for us to show up together, create accountability, and make progress side by side.

  • 📅 10:30am ET on 19 March

  • 🎟️ Exclusive to active Bosscraft members.

• Bosscraft New Member Orientation, your chance to get the lay of the land, meet some friendly faces, and understand all there is to access as a member. EXCLUSIVE to active Bosscraft members.

  • 📅 1pm ET on 24 March

  • 🎟️ Exclusive to active Bosscraft members.

• Making the Most of the Skoll World Forum 2026, a workshop put on by the team at BlackFox Global intended to support delegates and ecosystem participants in navigating the conference.

  • 📅 4pm CET on 25 March

  • 🎟️ Free registration here.

• Resilient Fundraising Strategies, a workshop put on by PartnersGlobal and Civic Safeguard Strategies on how nonprofits can strengthen financial resilience and reframe fundraising as a whole-of-organization effort.

  • 📅 11am ET on 26 March

  • 🎟️ Free registration here.

• Beyond the Burnout, a discussion of how burnout impacts work, motivation, and enthusiasm, facilitated by Boss Insights founder Whitney Kippes. to spotlight grassroots humanitarians. FREE registration here.

  • 📅 9am ET on 31 March

  • 🎟️ Free registration here.

• Bosscraft Peer Support Check-in, a monthly space to check in, share what’s working (and what’s not), and get encouragement from others walking a similar path.

  • 📅 9:30am ET on 7 April

  • 🎟️ Exclusive to active Bosscraft members.

• Bosscraft Co-working Session, a body-doubling call designed for us to show up together, create accountability, and make progress side by side.

  • 📅 10:30am ET on 23 April

  • 🎟️ Exclusive to active Bosscraft members.

🌿 Putting Down Roots

Discover permanent positions at social impact organizations doing work worth doing.

• Baltimore City Dept of Finance is looking for a Budget Director.

  • 💰 $185,000-202,068

• ChildFund International is recruiting for multiple resource mobilization positions (Advisor II and Advisor Sr.), which can apparently be based in any several different ChildFund countries.

  • 💰 Pay is based in non-U.S. currencies.

• Food for the Hungry is hiring a Senior Pricing Manager to join their business development team, to be based in Phoenix, AZ or Washington, DC.

  • 💰 Compensation information not available.

• JP Morgan Chase is hiring an Executive Director to head their housing access and affordability portfolio in their global philanthropy efforts.

  • 💰 $175,000-245,000

• Mercy Corps is hiring a Senior Advisor Major Gifts with flexible location (ideally in the Midwest or on the East Coast.

  • 💰 $86,000-100,000

• MSH is hiring a Business Development Specialist—which reads like an early career position—to be based in Arlington, VA.

  • 💰 $60,000-85,000

• Village Enterprise is hiring an Institutional Partnerships Manager to be based in East Africa (Nairobi, Kampala, Kigali, or Addis Ababa).

  • 💰 Compensation information not available.

• VEIC (clean energy) is recruiting for a Proposal Manager and Senior Proposal Manager.

  • 💰 $80,000-90,000 and $100,000-110,000

• WAMU—that’s the DMV public radio folks—is hiring a Major Gifts Officer to support their development office.

  • 💰 $90,000-110,000

• WILD Foundation is hiring a Conservation Networks & Facilitation Manager to support expanding international conservation efforts.

  • 💰 $70,000-80,000

• World Wildlife Foundation is hiring a Senior Director for International Fianancial Institutions to coordinate a global strategy on engaging the IFIs.

  • 💰 $200,000

🔒 Ready to focus your energy on the opportunities that actually bear fruit?

Paid members unlock The Trellis—our selection of short-term contracts, technical assistance roles, and fractional consulting gigs. Stop scattering seeds in the wind and start applying for roles that fit your specific craft. Join the to gather this week’s harvest.

Become a Paid Member

Read more

We start hording opportunities like they’re the last canned goods on the shelf before an impending storm.

This is a totally natural instinct. We’re clutching at straws. Every job posting, every lead, every “quick coffee,” every low-priority project. We say “yes” because “yes” feels like our chance to get back to safety.

But somewhere in our wisest self, we know that this is a bad move. We’ve probably read the research. Hell, we might have even written the book on building resilience. (Or at least a lot of funding proposals.)

Unfortunately, our stupid human brains don’t always do what we would like them to do. Sometimes we do the less-than-optimal thing because we’re just humans.

When we finally move into a new season, whatever safety we cobbled together starts to feel like a straightjacket.

If you’re feeling heavy, it might not be because you’re not doing enough work to find sustainability. It might just be that you’re doing too much of the work that was only meant to be temporary.

The Scarcity Hangover

Last year taught many of us to operate from a place of “just in case.”

• We took the client that didn’t quite fit our values because the bank account said we should.

• We said yes to the fancy freelance gig that was slightly out of our wheelhouse because we weren’t sure when the next one would come.

• We took the job that was “good enough” for right now.

• We said yes to the "quick coffee" that turned into a two-hour unpaid consulting session because we didn't want to "close a door."

The danger of the scarcity mindset isn't just that it makes us tired; it's that it makes us undiscriminating. When you are starving for security, everything looks like a feast—even the projects that are actually poisonous to your long-term goals.

Let’s give your past self some credit: that was a survival skill. You needed it. But do you still? Because you won’t be happy if you continue to subsist in survival mode.

Explosing the phantom fears is a critical step in preparing to retool your professional life. When we are back in the driver's seat, choosing to stop—choosing to say "no"—typically hits three pretty common fears:

1. The “Vanishing Opportunity” Myth

When we operate from scarcity, we believe opportunities are like Halley’s Comet: if we don’t grab this one, we won’t see another for 75 years. We fear that saying no to a “mediocre” client (or employer) today means the “ideal” client will never find us.

Reality Check: There are opportunities out there. You find them by investing time in meeting with the right people and spending time on marketing yourself. When you say “yes” to the wrong thing, it will actually force a “no” for the right thing by stealing both your capacity to do that marketing leg work and accept the ideal assignment when it materialized. You won’t have time to do the work you want to do most if you say yes to something you kinda hate today.

2. The Identity Crisis (The “Useful” Boss)

Many of us have built our self-worth on being the “fixer” or the “yes-person.” We worry that if we start setting boundaries, people will stop seeing us as high-performers. We confuse being busy with being valuable. Your classic people-pleasing behavior in which the person you strive to please never seems to be you.

Reality Check: As I noted in Thinking Like a Boss, true leadership requires firing yourself from the weeds. You cannot make time for the meaty work that you want to be doing if you allow every “quick ask” that comes your way to form a bottleneck. This also goes for having filled your week with 100% billable hours. You cannot think about longer-term strategy if you have no time or energy to do so.

3. The “Bridge Burning” Anxiety

We are terrified that a “no” is an insult. We think, “If I tell this person I don’t have the capacity, they’ll never ask me again, and they’ll tell everyone else I’m difficult to work with.” You say “yes” to every request because you believe that is the only way to maintain the relationship.

Reality Check: Professional “no’s” actually build respect. They signal that your time is a finite, high-value resource. For organizations, the strategic “no” isn’t a door slamming shut; it’s a roped off VIP area. For consultants the same is true: when you tell clients you have limited availability or are too busy to take on a request, you’re telling them that you are a valuable resource that delivers quality work.

Boss tip → pay it forward by pairing your “no” with a referral to someone else who may be available to help.

Relearning the Word “No”

Trimming back isn't about being restrictive or "exclusive"; it's about reclaiming your discernment. If you want to build a career that is actually sustainable, you have to stop treating your time like an infinite resource.

Relearning “no” can be terrifying. You’re turning your survival strategy on it’s head. After a year of saying “yes” to whatever came your way, you are going to need practice (and confidence) to say “no” to opportunities.

Let’s start with a few concrete questions you can ask to audit what is on your plate right now:

1. Identify the “Legacy” Yes-es: Take a good look at your commitments and your calendar. Which did you say yes to in the past? If you were starting your consulting practice or job search today, would you still say yes?

2. Check the “Being Nice” Tax: As I’ve written before, over-delivering often comes at the cost of your own breathing room. What boundaries did you maintain before sh*t hit the fan? Which boundaries do you really need to bring back to make your life feel better balanced?

3. The 20-Minute Financial Gut Check: Spend 20 minutes with your numbers. Often, the things we are most afraid to say “no” to are actually the least profitable when you factor in your emotional labor or the opportunity cost of taking on something that you are more interested in.

Chances are, you’ve identified a few areas where you need to adjust your approach. If you’re like me, you’ve identified a lot of devils disguised in good intentions.

What comes next is up to you.

Do you want to offload a project, client, or job application process completely? How would you go about that? Do you need a hard stop or a gradual phase out?

Is there something you want to bring in or do more of? Do you want to carve out time to talk to different people or find a different type of work? What would you need to take off your plate to find that time?

Which boundaries do you need to focus on enforcing? How will you communicate this to the individuals involved? Are they the issue, or are you doing this to yourself?

When you’re trying to decide whether to say “no,” listen for these phrases in your head. If you hear them, you aren’t making a strategic choice—you’re making a fear-based one:

1. “It’s just a one-off.” (The lie we tell ourselves when we’re about to let a project creep out of scope.)

2. “I should just be grateful for the work.” (The mantra of the scarcity hangover that keeps you from charging what you’re worth.)

3. “What if this is the last lead I get for a while?” (The phantom fear that ignores your actual track record of success.)

When you trim a plant, it looks bare for a second. It feels risky. But that bareness is focuses the plant’s energy on fewer branches, creating the space for new, stronger buds have the room to grow.

By saying “no” to the mediocre “yes-es” of last year, you are finally making room for the “hell yes” opportunities of this year.

The Conversation

This section is exclusive to paid subscribers and Bosscraft members.

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In the Bosscraft Podcast, I talk a lot about building careers that last—whether that is through freelancing or a 9-5. Sustainability can mean lots of things for different people, but for most it includes a certain amount of financial success. But what happens when the definition of success you’ve built starts to feel like a cage? Today, in our first edition of this new series, we’re taking a real look at the golden handcuffs.

The Card: Understanding the 10 of Pentacles

For those who may be newer to tarot, understanding the cards can feel like a major uphill battle. I encourage people to focus on the visual in the card as a starting place. What comes to mind? What elements of the image jump out to you? What feelings does the card give you? Try your hand using this weeks card: the 10 of Pentacles.

Before you ask: I use the Vindur Tarot deck, developed by Leah Pantéa, which is now out of print, but I strongly recommend learning a deck that strongly reflects the commonly used Rider-Waite imagery.

Whatever stood out to you first is inherently important to a personal reading, as this practice helps you tune in to your intuition. To understand a card further, it is helpful to look at the “anatomy” of the card:

• The Suit (Pentacles): In tarot, Pentacles represent earth or, more directly, the “stuff” of life. They govern the material world: your finances, your physical health, your home, and any “work” you physically produce.

• The Number (Tens): Tens represent the end of a cycle. They are the point of completion, legacy, and “perfection.”

• The Position (Reversed): Some people, myself included, read cards which are dealt upside down a little differently than their upright companions. These reversals can represent internal struggles, delays, or just a more nuanced interpretation of the meaning.

In the upright position, the 10 of Pentacles represents a point of completion and accomplishment in a financial or professional endeavor (the goal of many a boss). When reversed, it suggests that while the “wealth” (the jobs, the revenue, the status) might be there, the foundation is shaky. This reversal is a prompt to ask: Is this actually what YOU want, or is it just what is expected of you?

For mission-driven folks, the 10 of Pentacles reversed shows up when you’ve built a career that looks successful on paper (that’s the ten) but isn’t sitting right or giving you the boss vibes you hoped it would (there’s your reversal). You might be:

• Staying in a high-paying role (or less-than-aligned assignment) solely for the security, even though you don’t love the work.

• Achieving something you have worked for for a long time, only to realize that the title or pay bump or letters next to your name don’t fulfill you like you hoped.

• Aiming for a professional goal that you’ve outgrown or are ready to set aside.

• Tying your personal identity to you work so closely that any shake up in your professional life causes a crisis of identity. (oof, that one feels personal)

• Realizing that the standard of living you’ve worked for now requires so much maintenance it’s draining your peace.

The Bosscraft Take: A reversal isn’t a failure. It’s an audit. This card calls you to reassess what it is you are working for and whether you actually still want the goals you once set out. It’s time to unravel your self-worth from your professional (or financial) achievements and see if your ambitions are actually built on a pattern of burnout or disappointment.

The Conversation

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This week’s prompt: The 10 of Pentacles reversed asks us to look at where our “success” feels hollow. Is there a part of your consulting practice or career that looks great on paper but feels heavy or misaligned in practice? What would it look like to pivot your energy to invest in something that is more aligned to the values you hold today? What is one baby step you can take to move yourself toward that more aligned life?

I’ll be in the comments sharing my own "reversal" moment, which is a serious work in progress.

If I could give a card for the past year, it would certainly be the Wheel of Fortune.

This card is all about the cycles—the unpredictable ups and downs of life. I love this particular card for two reasons: first, its a great reminder that the only premanent feature of life is change, and second, it is a helpful nudge to stop fighting against external forces and insteal lean into the natural cycles taking place in the world.

The world has given me a lot of challenges in the past year—both challenges in my personal life, as my partner navigated multiple gender affirming surgeries amid a very anti-trans cultural shift, and challenges in my professional life, as the destruction of USAID and the federal workforce rit large resulted in industry wide changes and caused whole career paths to disappear basically overnight. This story isn’t new.

I know my regular readers know this journey. You’ve been right there with me, with your identities as humanitarian and international development workers being fundamentally disrupted. So much of our personal identities have been tied to our professional lives. And then they got all turned on their heads, basically overnight.

Throughout 2025, I kept cycling through new versions of myself.

First, as an event organizer. The idea was simple: we all have free time. We could all use a project. Let’s share some of the stuff we know! Corralling several former Bid Boss consultants to speak on everything from their areas of technical expertise to how to build a nomadic life led to Collaborative Learning Week. It was a lot of work. It was also a great distraction.

Then I picked up whatever freelance work was out there. I was fortunate to know a few people who needed support in basic web design—something I’ve been doing as side projects since I was about sixteen. I snagged a few clients providing advisory support on how to navigate new funders. The projects were a nice buoy when I really needed help staying afloat and helped me identify what client work I wanted to hold on to once I found a little stability.

Along the way, I did question whether I should get a “real job.” I’ve been working for myself since 2015, about half of that time as a solo freelancer and half of that time co-managing Bid Boss Consulting. But there are lots of ways to do the work I love, including through traditional employment. I’m still open to it, if the right thing comes along, but I spent a lot of time panic applying to whatever was out there. Big ole waste of energy.

The biggest throughline of the year has been how much I love coaching and teaching. I spent my unsolicited free time in April detailing all the course content that would eventually become the On-Ramp to Freelance Consulting course. It was wild to essentially word vomit 30+ guides, tools, and templates, plus a whole course curriculum. It was a huge vote of confidence to know that I had so much to offer.

I also started doing more individual coaching, as many folks starting freelancing looked to me as someone who knows the ins and outs and where not to bury the skeletons. Working with individuals as they start and grow their consulting practices had brought me so much joy.

This honestly shouldn’t have been a huge surprise, given that my first micro-pivot involved setting up the Bosscraft Consultant Community—home to both course-like workshops and peer coaching sessions. Consistently connecting with that community has been a constant source of comfort and companionship during an incredibly difficult year.

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All of this reinvention left me exhaused. It’s not working.

I kept hoping that the portfolio of work I’d developed would ramp up—or at least level out—but as the beginning of the year turned over I struggled to find enough people for a new cohort of the On-Ramp course and my big plans to offer “new year, new you” inspried coaching packages never found traction. And we all know that something can’t truly be sustainable if it isn’t financially sustainable.

I need to slow down. I need to focus on what is working. So that is what I’m going to do. Here’s what that means:

1. I’m cutting away the clients, courses, and content that aren’t working. Pruning back to allow other things to bloom.

2. I’m honing the things that have worked well, seem to be finding their groove, and offer some personal joy. That means coaching and the community are sticking around for good.

3. I’m cutting a clearer path, so that folks who find me understand what it is I offer and how I can help.

Step one of this process is dropping all my subscribers this (probably overly detailed) note to share a few things that are going to change here!

What does this mean for you?

Not a lot yet. Genuinely. You’re still going to be hearing from me here. You may see some new stuff too—especially for paid Substack subscribers. There will still be resources and workshops and insights. Lots of exclusive free stuff for my Bosscraft Community members, who will still get a healthy amount of face time with me. And I’ll still be available for individual coaching for the folks who need extra support.

But I’m hoping that you can sense a tone shift. I’m done reinventing. I’m going to let myself really settle into who I’m becoming.

I hope you’re getting to that point too.

💛