What I Learned From 4 Years of Late Entrepreneurship

All my life, I thought I thrived in systems. I believed I would never build my own business.

I wanted to make a difference, but I didn’t think I could do it through entrepreneurship. Until I founded Supportful.

I became an entrepreneur at 38.

It was a bold move. Some might say it was crazy.

I left a stable job for the rollercoaster ride of founding a company, all while raising four kids.

Four years in, I want to share three lessons from my late start in entrepreneurship.

Fail & Learn

I come from a traditional corporate background. Quick action, constant iteration, and pivoting were not part of my usual approach.

I hated failure after a 15-year career where every job was a step forward.

But as an entrepreneur, I had to change my mindset.

Failing and learning is the only way to move forward.

I learned to embrace failure. In sales, I tested many channels that didn't work (cold emails, salespeople, agencies, etc.).

I experimented with internal People initiatives: some succeeded, some failed.

I’m glad I tried. These experiences taught me what worked and what didn’t. Most importantly, I learned to try and fail fast.

Find Your Path

There are many "influencers" and self-proclaimed coaches out there. I heard so many conflicting opinions on what founders should do.

After trying different approaches, I realized this: every journey is unique.

I just needed to find my path.

What worked for others didn’t always work for me.

I learned to post content in my own style, lead my team in my own way, and simply be myself.

When I compared myself to young founders in their twenties, I envied their energy and excitement.

Late founders might not match that. And that’s okay.

Customers and investors value different traits in late entrepreneurs: maturity, experience, and the lessons we bring.

Look Back

Being in charge of your own fate (and your team’s) requires learning from every step.

I make it a point to regularly reflect on my journey.

I schedule weekly, monthly, and yearly reflection sessions. These are fixed in my calendar, and I protect the time fiercely.

Late entrepreneurs have the patience and maturity to make these reflection sessions work. Bonus points if you’re a parent entrepreneur too.

Every week, I spend 30 minutes on a strategy session focusing on one aspect of the company. It's typically a solo session, but sometimes ChatGPT sneaks in for help.

Every first day of the month, I review the previous month’s wins, failures, and lessons. This takes about 15 minutes and is always rewarding.

At year-end, I plan the next year by setting goals and planning on how to reach them.

Takeaways

To sum it up, my experience as a late entrepreneur taught me to:

1. Embrace failure and apply lessons in the next iteration.
2. Be authentic in everything I do or say.
3. Plan, assess, and strategize regularly.

I'd love to hear your thoughts on what entrepreneurship has taught you, whether you started early or late.

‍