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  • Writer's pictureJoel T. Sanders

How Would You Reinvent Your Company (or Yourself) If You Had to Start Over?

This question was posed to me in an entrepreneurs group called The 150. I faced the challenge of reinventing myself a year ago when I put my previous project—an app to help people with goal achievement— on perpetual hold.

Below are a few takeaways on how I'm reinventing my life as a fractional and outsourced COO. I don't pretend that this list is prescriptive for anyone else's situation; everybody has different life circumstances and values. I share this list only as an example of the power of reflective practice, a way of thinking that leverages life itself as your primary teacher.

All of this is quite ironic: as someone who deals with planning on a daily basis for my clients, I didn't plan this brought it to me.

Stop and talk with people.

When I put my goals app business on pause, I scheduled face-to-face interviews with fifteen people I admired, beginning each talk with this simple question: "What are your top two goals right now?" That single question led to people pouring out their hearts. I heard about the heartache of not getting pregnant, substance abuse, seeking love, and so much more. A common thread in every conversation was simply wanting "peace of mind." It was humbling.

I didn't know where those conversations would lead me. I just knew that deep and meaningful conversations with people always lead to something...and that whatever that something was would be the right thing. In retrospect, they led me to starting Momentum Ops and my present life.

All of this is quite ironic: as someone who deals with planning on a daily basis for my clients, I didn't plan this brought it to me.

Don't spend money—structure deals.

You can make money without spending money, and still have ownership by structuring creative deals. In my case, I started a consulting practice. In some of the businesses I consult, I take a minority equity stake in exchange for lower consulting fees.

Someone else takes on the bulk of the responsibility, capital risk, and full-time work, while I participate as a part-time partner with an upside if things really take off. I get to work with startups and small businesses, which I love, but have far less risk than I would have if I were all-in on a single thing. For many people, the wide variety of disconnected work projects would be too much, but I happen to love it.

Make your business fit into the lifestyle you want—no compromises.

Angelika Ilina (who is my wife and runs her own digital marketing agency) and I have been talking for more than a decade about living half of the year "somewhere on a warm beach" and the other half of the year in Colorado. For far too long, I've been putting this and other lifestyle decisions on hold, "until I get the business to where it needs to be."

But businesses are never where you want them to be, and often fail, as mine did last year. Despite being in much worse financial shape than we'd been in years, we moved to Puerto Rico last November for the winter. Ten months later, at the time of this writing, not only is our financial situation improving, it's thriving.

Speak with candor about your failures.

Your humility will earn your far more respect than your achievements. I've participated in entrepreneurship mastermind groups like The 150 and Entrepreneurs Organization for more than a decade. Every time I've shared my shortcomings or missteps, I've gotten multiple perspectives from people who experienced similar situations. Obviously, be discerning about who is truly a "peer" and who isn't.

Write a blog.

As you tinker and explore in business and in life, capturing insights and learnings in a blog helps you make creative connections you couldn't do in any other way.

When I blog, I'm essentially writing an essay for myself, as a way of bringing coherence and organization to my projects, my thinking, and my life. Knowing that someone else will read these words forces me to be more disciplined, ensuring that I write a coherent, organized, and sophisticated set of ideas about something important.

Writing isn't so much a way to demonstrate my knowledge to someone else so much as it's a way to come to understanding for me. To the extent that any of these thoughts are valuable to you, dear reader, is humbling and brings me great joy.

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