Life After Corporate: Six Months of Self-Employment Lessons

Six months ago, I traded corporate predictability for self-employment— and wow, have I learned a lot.

It’s been equal parts exciting, exhausting, and humbling. Some days I feel like I’m building something meaningful and exactly where I’m meant to be. Other days, I wonder what on earth I’ve done.

But I wouldn’t trade it for anything.

Things You Don’t Learn in Corporate

When you work in corporate, you get really good at your job.

When you go independent, you suddenly have about twelve new ones.

In the last six months, I’ve learned:

• How to build a website and troubleshoot everything that breaks.

• How to optimize LinkedIn and come up with content that doesn’t sound robotic.

• How to film videos (and how much I hate filming videos).

• That there’s an actual “Influencer Aisle” at Best Buy — complete with ring lights, tripods, and moral confusion.

• The joys of bookkeeping, business formation, contracts, pricing, insurance, and taxes.

• The pain of paying for health insurance out of pocket.

• The mystery of email warming and the endurance test that is spending hours on the phone with Microsoft.

• That Calendly and Canva might just be the best ROI of any business tools ever invented.

You learn quickly just how many departments were quietly holding you up in corporate life — IT, legal, finance, HR, marketing.

Now? They all live in your head.

What’s Been Hardest

Two things stand out.

First, sales and marketing. I knew it would be tough, but knowing and living it are two very different things. You can be highly qualified, but when you’re independent, you are the product. That takes some getting used to and I'm not sure it'll ever be something I'm comfortable with.

Second, self-doubt. There have been so many great days, and just as many when I’ve stared at my screen thinking, “What the hell did I do?”

But then I remember why I did it — to create work that’s meaningful and a life that’s truly mine.

What’s Been Most Rewarding

The conversations. I’ve connected with more people in the last six months than I did in years in corporate.

Hearing from others on the same path has been refreshing, grounding, and a reminder that no one really has it all figured out.

And the freedom — that’s the magic part.

Slow mornings where I can work out, enjoy my tea over the NYT crossword, listen to podcasts, and decide how the day will go.

That space has opened doors to things I didn’t have time for before — like writing a book.

It’s deeply personal, vulnerable, and unlike anything I’ve written before, but it’s also one of the most exciting projects I’ve ever taken on.

I’ve also had time to think about the shared project Eric and I started — Farm Table Health. Can you call it a business if it makes no money? (We’ll go with yes.) But it’s something we both love and are thinking more about shaping moving forward.

And there’s been travel — Italy, Portland, NYC, Amsterdam, Bruges, and Cologne — experiences that reminded me how good it feels to be curious again.

What I’m Still Figuring Out

I’m still learning how to narrow my focus — to balance building something new with keeping the flexibility I value most.

Contracting with large companies hasn’t been easy (I knew that going in), but I’m finding my way, one relationship and experiment at a time.

The biggest shift, though, has been internal: learning to trust myself, even when the path feels uncertain.

Six Months Into Self-Employment

Six months in, I can say this: it’s been the hardest, most rewarding kind of growth.

I’m proud of what I’m building, grateful for the people I’ve met, and genuinely excited for what’s ahead.

Even on the hard days — especially on the hard days — I know this is exactly where I’m supposed to be.