Why I’m Ditching the Five-Year Plan
You can’t build a sustainable future on a foundation of guesswork.
“Where do you see yourself in five years?”
It is the standard interview question. It is the slide every consultant feels obligated to put in their pitch deck. It is supposed to show that we are ambitious, organized, and in control.
But lately, I’ve realized that the 5-Year Plan isn’t a roadmap. It’s a trap.
Think back to five years ago. Could you have predicted the global shifts, the market changes, or the personal evolutions that have happened since then? Probably not.
When we cling to a rigid long-term plan, we aren’t actually planning for the future. We are just guessing. And when reality inevitably diverges from that guess, we feel like we’re failing. We white-knuckle the steering wheel, trying to force our lives back onto a map that is no longer accurate.
Going “Back to Basics” means admitting that we don’t have a crystal ball. It means trading the anxiety of the Destination for the clarity of the Direction.
The Compass vs. The Map
A map requires you to know exactly where the roads will be in 2031. A compass just requires you to know where “North” is right now.
Your “North” isn’t a revenue number or a specific job title. It is your values. It is the way you want your days to feel.
If you value freedom, your North might look like saying no to a massive contract that requires 60-hour weeks. If you value impact, your North might mean pivoting your services to a sector that needs you more.
When you lead with a compass, you are allowed to take detours. You are allowed to change your mind as new information comes in. That isn’t flakiness; it’s agility.
The Magic of the 90-Day Sprint
So, if we aren’t planning for five years out, what do we do? We plan for the season we are in.
I have shifted almost entirely to Quarterly Planning.
Ninety days is long enough to make meaningful progress on a big goal, but short enough to see the finish line. It allows you to:
Set an intention (e.g., “This is the quarter of Visibility” or “This is the quarter of Rest”).
Experiment with a new offer without betting the whole farm.
Reset when things go sideways (because they will).
Need a partner for your first 90 days?
If the idea of ditching the rigid map feels liberating but a little lonely, you don’t have to navigate it solo.
I created the Executive Coaching Calibration Series specifically for this kind of season. It is a focused, 90-day container where we meet bi-weekly to check your compass, untangle the sticky thoughts that are keeping you stuck, and help you find your footing.
It isn't a lifetime commitment. It is three months of dedicated support to help you trust your own direction again.
How Do You Want 2026 to Feel?
As we settle into this new year, I want you to look at your goals. Are they just a list of things you want to get? Or do they reflect how you want to be?
Success doesn’t count if you hate the way you achieved it.
If you are a freelancer and you’re ready to stop hyper-ventilating about the distant future and start intentionally designing the next few months, I have a tool to help.
It’s my Quarterly Reflection & Planning Toolkit. It’s not about rigid metrics. It’s about asking the human questions: What drained me last quarter? What energized me? What is the one thing that matters most right now?
Let’s stop planning for a hypothetical future and start showing up for the actual present.