(#041) How to Choose Between Equally Compelling Pursuits
Six Questions That Helped Me Bring Clarity to My Professional Choices
⏱️ 5 min read
Pozzolengo (Italy), January 28, 2023
For all the content out there on job seeking, career change, entrepreneurship, or the business of being a creative, there’s a remarkable emptiness on one crucial topic: how do you choose between two or more paths you’re already pursuing?
Most books and training materials focus on the drawing-board stage.
They typically lead you to take stock of three things, or a combination of: your assets, what you’re chasing, and what you want to escape from. At best, they offer frameworks to compare options before you’ve invested deeply in any one of them.
Herminia Ibarra’s Working Identity is the best book I’ve read on professional renewal. I just finished reading it today. She tells the least hyped-up story of career change I’ve ever encountered, and she captures the turbulence beautifully. But even there, the case studies are mostly about people who had one career through their 30s, 40s, or 50s, and then realized they wanted something else. They shifted from one path to another, through however long, non-linear, challenging journey.
But what if you’re not choosing whether to start something new, but between several things you’ve already started, each one equally compelling, albeit for different reasons?
That’s my situation.
Over the last two years, as I was searching for meaning outside of a role that no longer gave me much, I launched two start-ups. Along the way, I also rediscovered my passion for consulting—the work I did for most of my professional life before becoming a full-time executive in the company I co-founded and eventually sold.
And now I find myself with not one, but three different pursuits.
These aren’t just three projects, three clients, or three jobs.
They are three entirely separate paths of personal and professional growth.
My greatest challenge today isn’t finding a pursuit worth chasing. It isn’t even designing the next move.
It’s choosing which “baby” not to raise.
Because you can’t raise them all—not well, not at their best. That’s because their future success, both financial and spiritual, doesn’t depend entirely on me. So much of it is shaped by external circumstances, beyond my control.
This isn’t the situation of a founder with multiple ventures, each with teams, funding, and infrastructure, where the entrepreneur mainly plays a strategic or mentoring role.
This is the situation of ventures that still rely on the founder showing up every single day. And in that case, no business portfolio framework, no productivity hack, no “5 a.m. club” can make things work. You have to make a choice.
I don’t yet have the solution. But yesterday, I conceived and sketched a tool that gave me clarity, and I want to share it here.
At the center of the tool is what I call the Zone—that place where work feels frictionless, energizing, and nourishing across different areas of life. I identified six elements that drive us toward the Zone:
Income. Does this pursuit actually pay you? And if so, how much? Cash flow is different from potential, and it matters whether the work covers today’s bills or not.
Potential. Beyond current income, does it have the chance to take your wealth to the next level? To create savings if you don’t have them, to make you a millionaire if you aren’t one, or to multiply wealth if you already are? This is the classic start-up story: low salaries now, but maybe life-changing value later.
People. Who are you working with every day? Do they stretch you, challenge you, and teach you? Or do they make the journey lighter and more enjoyable? Or none of the above? It matters.
Routine. Do you actually like the texture of the work? The hours, the tools, the travel, the places it takes you. The small things add up. A pursuit might be exciting by subject and pay, but if the daily grind is miserable, it won’t last.
Resonance. Does it matter to anyone else? If you stopped tomorrow, who would feel the absence? Would anyone miss what you create, or seek you out for help? Resonance doesn’t guarantee success, but it feeds motivation in ways that money alone can’t.
Vision. Finally, the most abstract but maybe the most powerful. Do you have a vision you can’t unsee? Something that compels you to keep building even when the money, the people, the routine, and the recognition aren’t enough? Vision is often what carries legends across the darkest stretches or convinces an entrepreneur to finally start something new.
I rated each venture across these six dimensions on a scale of 1 to 5. (For qualitative matters, I find this the only scale that makes sense: more nuanced than 1–3, without the meaningless false precision of 1–10.) Then I plotted them on a radar chart.
(Now, here’s where I could tell you I spent time trying to create a slick acronym. But no, this one spells IPPRRV. Which sounds more like a printer error than a life framework. But I will proudly keep it. Too many gurus out there waste energy chasing cool names instead of being actually useful.)
As you might imagine, the chart didn’t hand me a clear winner. But it did highlight which path made the least sense to push into a higher gear.
For those of us who find ourselves engaged in more than one major pursuit, the constant sprints and turns of each venture, the competing demands, the unexpected urgencies, and the build-up of overdue priorities can easily blur judgment. It’s hard to keep a clear-eyed view of where to invest more.
My radar didn’t solve the entire dilemma, but it gave me perspective. It provided a sense of clarity and guidance I was missing.
If you are in the same place, hopefully running the same exercise can bring you useful insights (and I’d be curious to know what your own radar would look like).
L.F
(Read this article on Medium)
