5 Lessons I Learned from Starting a Business

I have been getting asked the same question a lot lately. I get a version of the question after almost every speaking engagement I deliver. The question usually goes something like this:

How did you go from what you first did as a career to doing what you do now?

I know career advice is a tricky subject, especially when it comes to completely changing lanes. Every professional has to navigate their own unique situation. I’ll share a few lessons that I learned on my own career leap from ad agency executive to entrepreneur.

Stop Telling Yourself ‘I Can’t’

I told myself over and over that I wasn’t an entrepreneur, and I really believed it. I had big dreams, but I didn’t think I was cut out to start a business. I know entrepreneurs and convinced myself that they were different. I was a corporate guy and needed the resources and structure in order to thrive and do my best work. In reality, the thought pattern of “I can’t” and “I’m not” is worthless. Five years after I started telling myself “I can’t,” I have started three companies and sit on the board of a start up now.

You can’t let self-doubt hold you back from your next step. If you want to make a meaningful change, you have to let go of self-imposed limitations and start thinking differently.

Embrace the Uncertainty

I cannot tell you the number of times I had the phone in my hand and was ready to call my old boss and ask for my job back — and it was a job that I didn’t even like! Launching in the middle of the great recession was unsettling. Transformation is scary, and there is always the risk it might not work out. Fast forward five years later: The fear is gone. It has been replaced by a feeling of excitement and exhilaration.

Confront your fear. Our big breakthrough moments usually exist at the edge of our comfort zone.

Be Prepared to Fail. You Will.

Those three companies I started? I promptly ran two into the ground. I had partners, papers, clients, contracts, commitments, obligations, expectations…all of it. Both times I thought it might be my undoing. Looking back on it, neither failure was that big of a deal. In fact, those experiences were exactly what I needed.

Now, I’m running the right business for me. My business is growing exponentially and the two missteps taught me everything I needed to know to get this one right. The truth is, I wasn’t failing. I was learning, growing and preparing for success.

Expect missteps. Learn from them, get better, and keep moving forward.

Your Network Is Your Net Worth

It pays to consider your peer group very carefully when you’re trying to strike out in a new direction. The people you surround yourself with will have a monumental impact on how you think, act and execute. I was fortunate to have people in my life that believed in me (even when I didn’t). They showed up with support, counsel and connections when I needed help the most and I will always be grateful. Their conviction turned into my confidence.

The coolest part of my journey has been meeting so many new and interesting people doing such extraordinary work. I will always carefully expand my Circle of Trust.

Nobody succeeds alone. Don’t have the right Circle of Trust today? Make a real effort to make that happen.

Start Today

I wasn’t fond of entering into the unknown. I liked the stability and predictable outcomes. Starting was the hardest part.
Five years and a lot of change later, I still have no idea of what is going to happen next. But now, the unknown is the fun part.

Take action now. If you want to do something different, there has never been a better time than today. These days, it really is possible to craft a different lifestyle and/or build a million dollar business from your kitchen table on the strength of your ideas and execution. Get started!


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