The Journey: #42 Choose the Right Journey

Early in my career, I didn’t know the differences between large corporate companies, small independent companies, and startups.

My priority after college was simple: get a job.

Ideally something that matched my major (or at least sounded like it did). Check.

After a few years working for a large publishing company, I decided to take a chance and join a small marketing agency, private and profitable. Then, I moved to a large public company. Then back to publishing. Then back to private. And finally, I took the leap and joined my first startup.

By the time I was 30, I had a little taste of everything.

And that’s where the real learning began.

Most people focus on the job. Or the manager. Or the compensation.

But I’ve learned to focus on the company.

Because the type of company you work for will shape your experience far more than your title or your paycheck ever will.

Public Companies

Structure. Stability. Scale.

Public companies come with predictability, clear processes, defined career paths, and often, great benefits. But they can also come with red tape. You’ll learn how to navigate politics, work within systems, and influence through structure. If you want to master discipline and scale, this is the environment for you.

Private Companies

Control. Consistency. Culture.

Private, profitable companies tend to move with intention. They aren’t beholden to shareholders, which gives them the freedom to make long-term decisions. The pace is steady, the expectations are clear, and success is measured by impact, not optics. You’ll learn how to optimize and operationalize.

Startups

Chaos. Creativity. Creation.

Startups are where you build the plane while flying it. The pace is fast, the change is constant, and your fingerprints are everywhere. You’ll wear 10 hats, learn 10x faster, and fail 10x more often. But if you love building, problem-solving, and shaping something from scratch, there’s nothing more rewarding.

Over the years, I fell in love with the startup life but I also learned that not all startups are created equal.

There’s a big difference between:

Early stage ($0–5M): pure chaos, pure creativity, everyone does everything.

Growth stage ($5–25M): building structure, defining process, hiring specialists, this is where I thrive.

Scaling stage ($25–75M): refining what works, layering in leadership, optimizing for repeatability.

Mature stage ($75M+): preparing for acquisition, IPO, or sustained scale, focus shifts from growth to efficiency.

My sweet spot is the $5–25M stage.

It’s where there’s enough traction to prove product-market fit, but still enough white space to build systems, teams, and process from the ground up.

That doesn’t mean I can’t succeed elsewhere, it just means I know where my energy is best spent and where I feel most alive.

Here’s what you need to know if you’re eyeing a startup:

• Understand the stage. A $5M company and a $50M company are wildly different experiences.

• Ask about funding and runway. How much do they have? How long will it last?

• Evaluate the leadership. Have they built companies before? How do they define success?

• Clarify your role. Startups change fast, know how your success will be measured and how your role might evolve.

• Assess your appetite for ambiguity. If you need consistency, you’ll struggle in early-stage environments.

If you’re looking for your next opportunity, evaluate more than the offer:

1. What type of company is it?

2. What stage are they in?

3. What type of environment will help you grow and thrive?

4. And most importantly, what kind of journey do you want to be on?

Because the truth is, the company you choose will shape the person you become.

So choose wisely.

Choose intentionally.

Choose the Journey.