How to Make a Career Decision

Three uncommon frameworks for deciding what’s next in your professional life.

This is where I work.

How My Career in PE Almost Ended Before It Began

This month, I became a Partner at ParkerGale Capital.

I feel pretty lucky. I found a job and a team where I feel like I belong, and they’ve asked me to stick around for the long haul. But funny enough, my career at ParkerGale almost never came to be. Three years ago, I decided to reject their job offer. Then I changed my mind. Here’s how my near-miss went down.

It was 2019. I was five years into my stint at Bain & Co. and was thinking about making a change. After a few months of networking and interviewing, I landed three offers: One for a new role at Bain, one with a VC-backed startup, and another to become co-head of ParkerGale’s Talent practice. Though I loved the startup’s CEO and the idea of shaping a growing organization, I couldn’t get excited enough about the business model. I politely turned the startup down.

The team at ParkerGale was different. That’s why I liked them. These people knew how to recruit. They knew their strengths, how to talk about their investing approach, and it was clear they cared deeply about who joined their team. Their job profile was detailed, thoughtful, and described not just a place in their organization, but a practice that needed building. During a three-hour panel interview, two of ParkerGale’s founding partners, Devin and Jim, dug deep into my background with the kind of rigor I respected (and, thankfully, had prepared for). There was also something about them — how they dressed, how they hinted at the balance between their work and their lives, even how their midcentury loft-like West Loop office was decorated — that was just… cool? “I think I want to work with these people,” I remember thinking, walking out of my interview. “I think I might want to be like them.”

But I had questions. I had recently completed a tour of duty working for Bain’s PE Group, and I had the scars to prove it. My time on Bain’s “PEG” team was the most exhausting and least balanced chapter of my career. I often arrived home from work after midnight, my mind anxiously spinning through the potential landmines hidden in my ramshackle excel models. At one point I started keeping a countdown calendar in my notebook, crossing off the days left in my rotation, one-by-one, like some kind of prisoner. I couldn’t wait to be free. Would ParkerGale’s brand of PE feel the same? Was I walking into something just as unsustainable? Wasn’t the easy answer just to stay put? From the outside-in, I could only guess.

I agonized over the decision. I made checklists, talked with mentors, consulted my family, and clumsily tried to evaluate the divergent paths offered by my two remaining options. But no matter what angle I examined things from, I still felt lost. My stomach churning, I decided to play it safe. I decided to stay at Bain.

My hands shook as I scribbled my talking points on a post-it note, outlining how I would turn down Devin and explain the rationale for my decision. I still have the post-it — nervous, uncertain doodles litter the edges of the paper, crowding my handwriting and exposing my conflicted state of mind. I was a mess.

Still, I pressed forward with my plan. I shut my office door, sat behind my desk, stared at my notes, tried to control my breathing, and prepared to make the call. But when I reached for my phone, I felt a powerful static move down the back of my neck and radiate into the rest of my body. My hand involuntarily jerked back as if I had just touched a hot stove. An invisible force field seemed to be emanating from the phone, pushing me away from making the call. While it’s difficult to describe the sensation, I just felt wrong. I called my wife and told her in a shaky voice: “I can’t explain why, but I think I have to take this job.” She understood. She told me to go for it.

I picked up the phone, called Devin, and noted that the sensation — this feeling of heavy resistance — was gone. After a stammering introduction, I croaked: “I’m in. Let’s do this.”

Why Traditional Decision-Making Frameworks Fail

I won’t reprint what Devin said next. Let’s just say he was excited.

So was I. I still am.

Working at ParkerGale has turned out to be the best move of my professional life. I joined a growing Operations team alongside several good friends, got to help rebuild our Talent practice, and then went back to my roots to start and build our Growth playbook, serving as coach, consultant, connector, and occasional therapist to our heads of sales and marketing. I love helping our portfolio companies figure stuff out. I love seeing the impact we can make together by getting the basic things right. The job is hard, but I love what I’m building and who I’m building it with.

Looking back, this decision should have been an easy one. I clicked with the team, was excited about the work, and have always felt a pull towards the unique challenges that small, growing companies face. So why the pain? Why was this such a tough call for me? Why did I nearly turn down the best job I’ve ever had?

Here’s what I think. The frameworks I was taught to use for big decisions simply didn’t work for me. I made a list of pros and cons, but the resulting ledger only magnified the stakes and made me feel overwhelmed. I talked to people I trusted, but they all seemed to consider my options through the lens of their own experiences and bias. I looked at best and worst case scenarios for each role, but, still, no clarity. The “you’ll know it when you see it” feeling I was promised never arrived. Gifted with two incredible opportunities, I didn’t feel fortunate — I felt maddeningly stuck. And, feeling stuck, I defaulted to what seemed like the most logical move— playing it safe and staying put.

It was only after consulting my last remaining resource — my gut — that I was able to make the right call. The strange physical sensations that arose when I reached for that phone turned out to be the clearest signal I could have asked for. They told me where I belonged and what I should do next. This clarity wasn’t built from reason, logic, or a checklist. The correct choice had been there all along; a faint but clear broadcast from inside of me repeating a single, un-ignorable message: This is where you can contribute.

How could I have better tuned into this signal? How can we make sense of the overwhelming amount of noise and competing advice we encounter when shaping our careers? How can you get in touch with what you really want to do — what you’re meant to do?

That’s a hard question. I don’t have an answer for you. Not the answer, anyway. What I do have are a few useful tests.

The Three Tests

All of us have moments where we feel lost or unsure of where to go next in our careers. In these moments of uncertainty, we yearn for something to cling onto — to ground us and help sort through our competing feelings and logic. These three tests can help provide that structure. They’re the same simple frameworks I offer to friends and colleagues trying to figure out “what’s next” for them. They’re the ones I wish I had already discovered when I was dealing with my own crossroads. They would have helped me then. I bet they’ll help you now.

A quick disclaimer — these tests aren’t meant to reveal your perfect career path. I’m not promising an epiphany or a magic formula. I can’t reduce your professional life to a paint-by-numbers exercise. (Anyone who claims otherwise is lying to you.) But I hope that they will reveal something for you — just as my aborted phone call did for me. These tests aren’t a treasure map. They’re more like a roughly-calibrated divining rod. They’ll help cut through the noise and clarify the subtle difference between I should and I want. They’ll help you hone in on the next small step that quietly promises to make you a little more like the person you already want to become.

With that, here are the three tests.

Test 1: The Claustrophobia Test

An executive coach once told me:

“Good decisions feel like you’re opening something up. Bad decisions feel like you’re getting boxed in.”

We’re all in search of purpose, mastery, and autonomy in our work, and a feeling of claustrophobia — of being “boxed in” can help you predict how those factors will show up in a new role. Feeling boxed-in can be an intuitive signal that you might not have the ability to shape your work in the way you want. That you might be at risk of becoming a cog in the wheel— trapped drudgingly working in the business instead of on it. Or that you might be unintentionally pigeonholing yourself into a particular industry or role.

Looking back, staying at Bain felt more “closed” for me while going to ParkerGale felt more “open.” Why? While Bain offered interesting work inside a prestigious firm, ParkerGale offered something nebulous but more intriguing. The PG team had written my job description as a series of open-ended problems to be solved, but admitted they didn’t know quite how to solve them yet. That felt exciting and expansive. That clarity around the problem paired with the freedom and responsibility to explore was ultimately, I think, the reason I took the job. Yet I only had words to describe it after the fact. Here’s my advice: Don’t make the mistake I did. Take the time to notice this sensation — of how an opportunity feels. More open? Or more closed? This simple thought experiment might be the only tie-breaker you’ll need.

Test 2: The Apprenticeship Test

If you were born 300 years ago, your professional path would have looked very different. You wouldn’t have started your career at a company. You would have begun as an apprentice, working under a master craftsman —maybe a blacksmith, a scholar, a chef, a merchant, or a musician. Your apprenticeship wouldn’t have come with a career path or development plan. Your job would have been simple: Absorb the techniques of your master while doing their grunt work. Eventually, the quality of your work would approach, and hopefully match, your master’s standard. At that point, you were ready to go off on your own. Your apprenticeship would have reached its successful end. Progress inside an apprenticeship followed a two-step process: Find someone to model and then, over time, “become a little more like them.”

Apprenticeships back in the day were family affairs. You didn’t interview for a career — you were born into it. Not so anymore. You have a choice. But in making that choice, it still pays to consider your career from the angle of apprenticeship. More specifically:

• What standards do you want to adopt for your work?
• What does the “idealized professional version of you” look like?
• What skill or discipline do you want to gain mastery and confidence in?
• Who would you be happy becoming a little more like?

The simplest recipe for a fulfilling career might just be two steps: (1) Know the answers to these questions and then (2) Seek out the team and environment that nudges you in their general direction. When friends are wrestling with two very different opportunities — say, one role as an investor and another in a startup — I will often challenge them to consider the apprenticeship test. Forget the salary, prestige, and this made-up notion of the perfect career path for a minute. Who do you more want to apprentice under? That question has never not led to a good conversation. More than once, the person I share it with has decided in their next breath which role to take. Not one has regretted their decision.

Test 3: The Garden Test

Somewhat recently, a good friend from my consulting days was listening to me lament about a low point at work and a few options that had surfaced elsewhere. He noticed that I kept talking in terms of best-case outcomes — asking questions like:

• Where would I make the most money?
• What job would supply the most prestige?
• Where would I have the best chance to get ahead?

My friend stopped me and said: “Paul, you’ve reached a point where life doesn’t have to be a race. It can be a garden.” There’s no way to measure yourself in a garden, he continued. A garden can’t be won. It can’t be optimized. You can’t succeed or fail in a garden. Working in a garden is about choosing what to attend to and what to cultivate. Is today about your roses or your tulips? There’s nothing good or bad, better or worse, about either choice. In a garden, it’s simply about what you prefer to work on at that time.

As he said this, I could feel my brain’s circuitry being rewired. I had spent the last 8 years since business school running a race, I thought. A race to prove that I belonged. A race to get promoted. A race to finish the next project, get recognized, and keep moving up. A race to distinguish myself, earn my place, and win.

While I still believe in the value of a competitive spirit, it was freeing to consider my career in this new light — through some new, simpler questions:

• What do I want to master?
• What’s worthy of my time?
• What am I drawn to?

There are times where you have to grind it out in life. There’s no avoiding it. My 6-month slog in PE consulting was torturous, but I’m glad I did it. As I’ve written before, you can’t build resilience without managing a few lows. But I now believe that after paying your dues and surviving a professional crucible or two, it’s both healthy and necessary to recognize not only what you’ve achieved, but also what you’ve earned: A right to work on what interests you. As Ray Bradbury once wrote: “That’s the whole secret; to do the things that excite you.” So when weighing several professional options, ask yourself this: What excites you more? There may be no better test for what to work on next than that single question.

Final Thoughts

I read recently that the quality of your life is determined by three basic choices: What you do, where you live, and who you’re with. I’ve noticed people tend to seek the most counsel from others in deciding “what we do.” There’s a good reason for this. Leaning on our inner circle as we decide where and with whom to work helps us feel supported and allows us to draw on the experiences of those we trust. But that counsel comes at a cost. Co-opting the people we know in our career decisions introduces pressure, expectations, and competing logical arguments; all small but noticeable burdens that we must balance, carry, and rationalize. Suddenly a choice about where to work isn’t just about you — it’s also about honoring your relationships and creating closure with others. That’s hard.

It’s also, in most cases, unnecessary. If your experience is anything like mine, you probably know the right call already. You have the answer, deep down in your gut, directing you invisibly towards what you want to do next— what you’re meant to do next.

All you have to do is listen.