One Year Into Entrepreneurship: What I Learned Leaving Corporate

One year ago, I made the leap from a secure corporate job to start my own business, ATW.

Everything took off faster than I planned, and it quickly became clear I was just a vessel for something much bigger than myself.

I explore this further in The Power of Asking.

In this article is the story to how I started running my business, and the lessons I learned.

Life Before

A year ago, I had good money, job security, and a nice life in an industry that had always supported me. But I couldn’t shake the feeling that something was off, even though plenty of people told me I should just be grateful.

Then I heard Sahil Bloom say something that hit home:

The worst thing isn’t failing at your dream, it’s living out someone else’s dream well.

That’s exactly where I was.

Always Ready

The first lesson I learned? Don’t convince yourself there’s a right time or that you can prepare for everything.

You need to be prepared, but also be prepared to feel unprepared. That’s okay and it’s part of the process. You’ll never feel completely ready, so don’t wait for that moment to come.

Bootstrap Smart

Here’s something that might surprise you: you don’t need to accept money or take on investors right away, especially for a service business. I started ATW with less than $5,000 in total startup costs, including insurance, website, state filings, and QuickBooks. Keeping overhead as low as possible was key because it absolutely can be done.

One of my biggest surprises was how many people offered money when I said I was starting a business. Be ready for this and know what direction you want to take. We probably could have grown faster with outside capital, but I didn’t want to be responsible for other people’s money before proving it was viable. Plus, doing things organically gave me space to implement systems without total chaos.

Do Everything

This next reality check was harder than expected. In the beginning before you have employees, you’re doing everything. Full stop.

If you’re leaving corporate to start a business, this likely means doing tasks you’ve had someone else handle for years.

I hadn’t fully thought this through, so be ready for it.

Outsource Strategically

As things start moving, you’ll want to start outsourcing what makes sense before hiring full-time employees. I knew things like a bookkeeper were necessary from day one, and I’m glad I spent the money. It’s not something I’m good at, and I would have wasted too much time trying to do it myself.

A lot of people suggest admin and scheduling help, but that doesn’t take much of my time or brainpower, so I kept doing it myself. The key is figuring out what makes sense for your specific situation and skills.

Ask Everything

Don’t be afraid to reach out for help. I contacted so many people in the week between deciding to quit and launching ATW. Yes, it was just a week because I had to move quickly. If I gave myself six months to think about it, it never would have happened.

Most people want to help, especially entrepreneurs who want to help new entrepreneurs. You’ll get more support than you expect if you just let yourself be open to receiving it.

Conclusion

The next chapter looks like continuing to grow, making a few more hires in 2026, and starting the process of me stepping back from running everything day to day. This is my biggest challenge, so feel free to hold me accountable.

Looking back at this year, here are the key lessons I learned:

Don’t wait for the perfect time – be prepared to feel unprepared
You can start a service business with less than $5,000 in startup costs
Be ready to do everything yourself in the beginning
Outsource strategically based on your skills and time constraints
Ask for help – entrepreneurs want to support other entrepreneurs
You’re probably more prepared than you think

I had no idea what to expect when I started, but everything so far has been better than I ever imagined. I would never suggest anyone take advice from me, and I often advise against it. But there’s a good chance something amazing is waiting for you on the other side of whatever is stopping you.

Ready to make your move? Stop waiting for the perfect moment and start preparing for the imperfect but exciting journey ahead.