How to Take on Your Dreams Step-By-Step
January 4, 2019

Four months ago I was laid off from my job at a tech startup. I had been cutting my teeth on the sales team for 18 months when, on a hot day at the end of August, it all came to a crashing halt. There had been a reorganization and my position was being eliminated – or rather I was being eliminated.

For the next few days I experienced a wide variety of emotions – disbelief, frustration, anger, confusion. Finally, as the dust settled and I came to grips with my situation, I was forced to look forward. What now? I thought.


My entire career up to that point had been in sales but my heart was never in it. There was only one reason I’d go back: the money. This seemed like a valid reason at the time. After all, I did live in New York City and rent was right around the corner. On top of this, I had gotten used to my cushy lifestyle that was supported by regular commission checks.

But there was another idea – a crazy idea. What if I became a full-time coach? I had begun coaching people on the side for a couple of years. At first I had worked pro bono but slowly started taking on paying clients. I absolutely loved coaching and felt I was great at it – perhaps far better than I ever was at sales. But, what would this mean? I’d have to build a business? What about my secure income?

As September marched on, I weighed my options, my mind swirled with all sorts of contradictory thoughts. My rational mind told me I needed to go back into sales until my coaching business was more stable. My aspirational mind told me to forget sales and build my coaching business now. 


One day, in late September, I decided to take a break from my deliberation. I spent the day walking Central Park. I started at the top up in Harlem and made my way all the way down to Columbus Circle. As I walked, I found my mind continually jumping back to my business idea. No matter how much I tried to suppress them, questions kept popping up. How can I make enough money next year? Can I get to 20 clients? Who will mentor me? Do I need more training?

Frustrated with myself, I took a seat on the ground under a giant oak tree and closed my eyes. I hadn’t even officially started this business yet and it already seemed overwhelming. If this was how I’d feel the entire time then I wanted no part in building it. After a short rest, I got up and began walking again.


Hours later, I reached the Sheep Meadow just north of Columbus Circle. My day’s journey was almost complete. I squatted down on the grass and admired the shimmering midtown skyline as dusk settled before me. I took out my map of the park to admire how far I’d come. I had explored every part of Central Park from the Harlem Meer to Strawberry Fields. What an incredible day.

I was about to fold up my map and head home when something occurred to me. How had I accomplished this so effortlessly? I did it without a worry or sense of overwhelm. I simply just did it – step-by-step.

That was it! I realized in one swift moment. I never thought about the entire journey through the park. I only focused on what was directly in front of me.How obvious – I thought.

This same “step-by-step” mentality had helped me complete the Boston Marathon and trek 5 days to Machu Picchu. In all of these cases, if I had started worrying about what was 10 miles ahead, I would’ve stopped before I got started.

I realized then that this would be the same with my business. If I were to start this business, I could not worry about next year, next month or even next week. I must only focus on the one task directly in front of me. This would make it all manageable again. If the “step-by-step” mentality got me this far, then surely it could guide me to building a successful coaching business.


Finally, I stood up and stretched. My head was buzzing again – but not with overwhelm or discouragement. It was buzzing with possibility. I walked down the slope of Sheep Meadow to Columbus Circle and got on the subway to head home.

I was now ready to take on this new journey… step-by-step.




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