Some Changes Coming to Boss Insights
Because every boss needs to reflect, plan, and pivot sometimes.
As many of you know, I have a particular penchant for tarot cards. I do a weekly card pull for the Bosscraft community members, consult the cards when I need to tune into my intuition, I’m even an occassional attendee at local tarot club that meets at a brewery in my Baltimore neighborhood.
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.
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:
I’m cutting away the clients, courses, and content that aren’t working. Pruning back to allow other things to bloom.
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.
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.
💛