The Question That Changed My Entire Career

For most of my career, when I thought about what came next, I started with the same question most of us probably ask ourselves: What should I do?

What job should I apply for? What am I qualified to do? What would be the logical next step based on the jobs I've already had, the experience I've accumulated, and the things someone might reasonably look at on my résumé and decide I know how to do?

It seems like a perfectly reasonable way to build a career, and for a long time I didn't question it.

Until my career stopped being particularly logical.

I spent more than a decade working in nonprofit youth development, where my work evolved from programs and events into volunteer support, member experience, strategy, retention, growth, training, and leadership. I loved solving problems, figuring out why something wasn't working, building something better, and helping people have a better experience because of it.

If you had asked me back then what I did, though, I probably would have answered with my title.

That was how I understood my career too.

Then, in 2020, that chapter ended unexpectedly when I was laid off.

There are moments in your life that seem insignificant while they're happening but somehow stay with you, and one of mine is carrying a box through a parking lot with the things that had accumulated in my office: a lamp, family pictures, my planner, my purse, and all the random pieces of a life I had assumed I would be returning to.

I wasn't.

And suddenly What should I do next? became a much harder question.

When Your Résumé Doesn't Know What to Do With You

What happened next certainly wasn't part of any career plan I had ever created.

I started baking cookies.

What began in my kitchen grew into Cookie in a Hurry, at times, replaced a full-time income. I baked, bought supplies, created packaging, built systems, handled deliveries, marketed the business, worked with customers, developed products, solved problems, and figured out approximately twelve things a day that I had never needed to know how to do before.

On paper, it looked like I had gone from nonprofit executive to baker. But that wasn't really what happened.

I was still doing many of the things I had always been good at. I was building something. I was figuring things out. I was looking at what people needed and creating an experience around it. I was connecting with people, solving problems, developing systems, marketing ideas, and finding ways to make something grow.

The setting had changed dramatically.
I hadn't changed nearly as much as I thought I had.

Eventually another opportunity took me into corporate strategy at a telecommunications company, which, again, looked like another pretty significant career change. I went from youth non-profit to cookies to telecommunications, which is not exactly the career path anyone is going to diagram for you at a college career center.

But once again, underneath the job titles and industries, I found myself doing familiar things: looking at information, finding patterns, thinking strategically, solving problems, working across teams, and trying to figure out what could work better.

Then I was laid off again. And this time, when I found myself asking What should I do next?, something about the question didn't feel right anymore.

Because I had enough evidence by then to know that my career wasn't nearly as random as it looked.

Maybe I Had Been Asking the Wrong Question

When you look at my résumé through the lens of job titles and industries, my career can look a little all over the place.

Nonprofit leadership.
Bakery owner.
Corporate strategy.
Entrepreneur.

For a while, I think I saw it that way too, and when I was trying to figure out what came next, I kept looking at those individual experiences and trying to decide which one I was supposed to build from.

Should I go back to nonprofit work?
Should I look for another corporate strategy role?
Should I build another business?
Which version of my career was the "right" one?

Eventually, though, I started asking myself a different question:
What have I always been good at that I've always taken for granted?
That question changed everything.
Because when I stopped looking at the titles and started looking at myself, I could see the thread that had been there the whole time.

I figure things out

I can walk into something messy and start seeing how the pieces connect. I ask questions. I look for patterns. I see possibilities. I like taking something that feels overwhelming or unclear and helping someone get to the point where they can say, Okay. Now I know what to do.

I had done that with volunteers and teams. I had done it with programs and organizational strategy. I had done it with data. I had done it while building a cookie business in my kitchen. I had done it with other business owners, sometimes without even realizing that what felt like an ordinary conversation to me was helping them see their business differently.

The industries had changed.
The titles had changed.
The thing I naturally did hadn't.
And that's when Who am I? became a much more important question to me than What should I do?

We're Really Good at Starting With the Opportunity
Think about what happens when you decide you might be ready for a new job.
Most of us open a job board and start searching for titles that resemble the ones we've already had, and then we read through job descriptions looking for the places where our experience matches what someone else says they need. We think about whether we're qualified, whether the salary is right, whether we can do the job and, eventually, whether someone will choose us to do it.

I know this cycle very well.

After my corporate layoff, I applied for job after job, and every application forced me to make my career fit neatly onto a page for someone who had never met me. The question became which box I belonged in and which parts of my experience were relevant enough to convince someone that I belonged there.

But the more I tried to figure out which title fit me, the more I started realizing that maybe a title wasn't the thing I needed to understand.

Because you can be incredibly qualified for something that makes you miserable, and you can be really good at work you don't particularly enjoy.

You can also build a successful business that creates a life you don't actually want, or work incredibly hard to reach a position you once thought you wanted only to discover that the actual day-to-day experience doesn't fit you at all.

Being capable of doing something and wanting to build your life around doing it are not the same thing.

Who Are You Without the Job Title?

This question sounds simple until you actually try to answer it.

If I take away your current job title, your previous job titles, your degree, your certifications, and all of the other labels we use to explain what we do professionally, what is left?

What are you naturally good at, including the things you've probably stopped noticing because they come so easily to you?

That was the part I had missed in my own career.

I had spent years accumulating experience without realizing that the most useful information wasn't necessarily the experience itself. It was what those experiences had taught me about how I operate.

When I looked back at my years in nonprofit leadership, the cookie business I built after my first layoff, my time in corporate strategy, and eventually the business I’m building now, I stopped seeing a series of disconnected careers and started seeing the same person showing up in very different environments.

That distinction matters.

Maybe you're the person who walks into something completely disorganized and immediately sees how the pieces could fit together. Maybe people naturally come to you when they need to talk something through because you ask the question that helps them see the situation differently. Maybe you're constantly introducing people because you instinctively recognize who should know each other, or you're the person who can take a complicated idea and explain it in a way that suddenly makes sense.

We tend to dismiss those things because they don't feel particularly impressive to us.

They're just things we do.

But sometimes the things you assume "everyone can do" are precisely the things you should be paying attention to.

Just Because You're Good at Something Doesn't Mean You Have to Keep Doing It

There's another piece to this that I've learned through all of my different chapters, which is that identifying what you're good at isn't enough.

You also have to decide whether you actually want to keep doing it.

There are things we become good at because we've done them for a long time, and when we're looking for our next opportunity, those are often the things everyone else immediately sees. You have experience doing X, so naturally your next job should involve more X.

Except experience is valuable, but it doesn't have to become a life sentence.

What's why Who am I? has to include more than What am I good at? It also has to include What do I enjoy? What drains me? What gives me energy? What matters to me now? How do I like to work? Who do I like working with? What kind of problems do I enjoy solving? What do I want my actual life to look like?

Those answers are allowed to change.

Mine certainly have.

Your Career Is Part of Your Life, Not Separate From It

One of the biggest things all of these different chapters have taught me is that I don't want to make career decisions in isolation from the rest of my life anymore.

A job isn't just a title and a salary. It's the time you wake up, how much control you have over your day, the people you spend your time with, the stress you carry home, the energy you have left for your family, and whether the way you're spending such a significant portion of your life feels connected at all to the things that matter to you.

Entrepreneurship isn't automatically the answer either, because starting a business doesn't magically create freedom if you build a business that requires you to spend every day doing work you hate.

The goal isn't necessarily to find the perfect job or start the perfect business.

I think the goal is alignment.

It's understanding yourself well enough that you can start making choices that fit the person you are and the life you're trying to build.

And that's ultimately where Lettuce came from.

It didn't come from me deciding that everyone should quit their job and become an entrepreneur, because I don't believe that at all. It came from my own experience of realizing how easy it is to keep asking What should I do? without ever stopping long enough to understand the person you're trying to answer that question for.

Then You Can Ask What You Should Do

Once you start understanding who you are, What should I do? becomes a much more useful question because you're no longer asking it in a vacuum.

Instead of searching for any job you're qualified for, you can start looking for environments where your strengths, interests, priorities, and personality actually have room to work together. Instead of asking which business you could start, you can look at the intersection between what you're good at, what you enjoy, what other people need, and the kind of life you're trying to create.

You can also look at your past differently.

I don't look at the stops at the non-profit organization, Cookie in a Hurry, telecommunications company, my layoffs, and Lettuce as a series of disconnected starts and stops anymore.

They are all part of the same story.

Every one of those chapters taught me something about what I'm good at, what matters to me, how I work, what I don't want, what I'm capable of figuring out, and what I want to carry forward into whatever comes next.

My résumé tells you where I've been.
Understanding myself tells me where I might go.

So if you're trying to figure out your next chapter and you've been asking yourself What should I do? over and over again without getting anywhere, maybe you don't need to work harder at answering that question.

Maybe you need to put it down for a little while and ask a different one.
Who am I now?

Not who was I when I chose this career fifteen years ago, not who does my résumé say I am, and not who would make the most sense to a recruiter looking at my experience on paper, but who am I today, after everything I've learned, everything I've tried, everything I've succeeded at, everything that hasn't worked, and all the ways my life and priorities have changed along the way?

You might not finish answering that question with a new job title or a perfectly formed business idea, and that's okay.

Because before you need an answer, you need a direction.

And if there's one thing my very-not-straight career path has taught me, it's that sometimes the best way to figure out where you're going next isn't to start by asking what you should do.

It's to finally understand the person who's going to do it.