Career hack: Level down to level up

How do you specialize in being a generalist?

When I quit my last W2 job, I had no idea how to position myself. I built my career by being the one who parachutes in and saves the day. Now I was back in the plane, parachute packed, and I had no idea where to jump.

What exactly would people pay me for? How do you market range, judgement, and experience? 

I had no idea.

I needed reps, not a niche. 

So, instead of marketing myself as an expert, I leveled up by leveling down. 

I treated my first two years as a consultant like a paid apprenticeship. I took jobs I was overqualified for so I could try new things and learn from others. The people who hired me shared their world view, and in turn I returned exceptional results under their brands. 

I was there to collect context, not credit. 

Every success was a proof point about my own economic viability. When my work was the inflection point in someone else’s business, that meant I was on to something. Meanwhile, I gathered data about what worked and what didn’t in the various models I worked under.

I was strategic about staying curious, but not naïve. The plan wasn't to stay second banana forever. It was to earn as I learned rather than paying for my mistakes.

And I don’t regret it. For two years, I did the reps. I worked with fast food restaurants and investment firms, landscapers and doctor’s offices, tech startups and news rooms. I worked with nonprofits, for-profits, and no-longer-making-a-profits. 

Along the way I met all kinds of people and learned how their world views informed their businesses. I learned from their successes and their failures, and carried those lessons forward to my next clients. Best of all, I learned what people would pay me for.

What started as a step back became a growth hack. When it came time to brand my service, I knew exactly what I was good at, where there was a gap, and what people would pay for. 

If you’re struggling to find product-market fit, you might be too far removed from the problem to see it clearly. The beginner’s mindset isn’t about inexperience. It’s about choosing to keep learning. 

Climb down the ladder a few rungs and spend some time working in the mines. You’ll come back with enough gems to be set for life.

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