5 Costly Lessons I Learned My First Year as a Founder

Year one of running my own business taught me more than any book, course, or podcast ever could.

I came in with a strong network, over a decade of recruiting experience, and a clear plan.

But growth rarely follows a straight line—and like many who take the leap into building something from scratch, I encountered my share of pivots, realizations, and lessons learned the hard way.

Here are five of the biggest ones—shared so you don’t have to learn them the hard way too.

1. I waited too long to elect S-Corp status

I launched as a single-member LLC—quick and easy. But I didn’t elect S-Corp status early enough, which meant I missed out on tax advantages and had to navigate a painful correction process (including faxing documents to the IRS in 2025).

Takeaway:
If you're bringing in consistent income, speak with a qualified CPA early. The right structure can save you thousands and simplify how you pay yourself. Keep more of your hard-earned money!

2. I unplugged from LinkedIn—with no plan

I took a digital break in Q1 while traveling. While the reset was necessary, I didn’t schedule posts or repurpose top-performing content.

The result? Lost visibility, missed opportunities, and unnecessary rebuilding just a few months later.

Takeaway:
Take the break—but plan ahead. Let your best content continue working for you in the background through scheduling and automation.

3. I didn’t have LinkedIn Premium

I didn’t realize that service requests and leads were getting routed into a Premium inbox I wasn’t checking. I missed potential client connections for months.

On top of that, I went inactive—and LinkedIn’s algorithm didn’t reward the silence.

Takeaway:
If your business depends on inbound, visibility, or outreach—Premium isn’t a luxury, it’s a lever.

4. I launched with extreme confidence—and got humbled

I had momentum, clarity, and vision. But I still hit resistance.

There were pivots. There was shoveling behind the scenes. There were moments of doubt.

But there was also unexpected upside: I built new skills, rediscovered my creative muscle, and got sharper in ways I hadn’t anticipated.

Takeaway:
Entrepreneurship—whether as a founder, operator, or builder—is a full-contact sport. Growth lives in discomfort.

5. I used to focus on the destination. Then the journey. Now? The people.

Earlier in my career, I chased outcomes—titles, milestones, wins.

Then I shifted to valuing the journey—process, learning, progress.

But today, I see what really matters: the people you build with.

Strangers become acquaintances. Acquaintances become friends. Friends become like family.

Takeaway:
Trust the process. Focus on your people.
Your network is your net worth.

These lessons reshaped not just how I run my business—but how I think about growth, relationships, and long-term value.

If you're building something, leading through change, or navigating a new chapter—I’d love to hear what you’ve learned too.

I recently shared these lessons as a LinkedIn post with a carousel of photos and reflections that gives a more visual peek into the journey.

Feel free to check it out—and if it resonates, drop a comment or share your own takeaways.

Let’s connect, trade notes, and explore how we can collaborate to solve meaningful problems and help each other win.