06/23/25
Remember 5 years ago when the entire world shut down?
Feels like a long time ago, right?
In March of 2020, COVID-19 was declared a global health emergency, and a consulting opportunity I was working on for months came to an end.
I was one year removed from corporate, and while I had success in consulting, I didn’t like how I needed to run everything by executive leadership.
I wanted more creative freedom.
Since the market for keynote speakers was extremely difficult given the pandemic, I decided to pursue coaching.
I knew I could help people struggling through the pandemic continue to do meaningful work while avoiding the pitfalls of stress, anxiety, and overwhelm, but I didn’t know where to start.
I hired a coach who told me that the only way to build a successful coaching business was to reach out to people directly, but boy, was I hesitant to do so.
I had years of sales experience, but I still felt so much resistance to sending a connection request or DM on LinkedIn.
How could I overcome this resistance to take this necessary action to build my business?
What I decided to do was turn it into a game.
I grabbed playing cards, and for every connection request I sent, I put a card face down in the left pile.
Every time I asked if someone would like to have a call with me, I put a card down in the middle pile.
Whenever I schedule a call, I put a card down on the right pile.
At the end of the day, I would count up my cards and add those numbers into a spreadsheet.
And just for fun, I would turn over the cards and see what kind of poker hand I could make.
Sometimes I got three of a kind, other times a flush, and even a few straight flushes.
The next day, I would do my best to beat the numbers from the previous day (ideally, adding more cards to the pile on the right).
After implementing this, I went from having zero clients to over 10 clients within three months.
In dollars, that meant I went from earning nothing, to exceeding $10K a month within 90 days.
Years later, I still have a successful coaching business, and I’ve expanded my offerings to include keynotes and interactive workshops.
The point?
If you’re feeling resistant to taking uncomfortable action…
Make it fun.
I didn’t like sending DMs.
It was so uncomfortable for me.
By making a game out of it, I was able to take action despite the discomfort, which led to positive results.
My business would not be what it is today if I hadn’t made up this game and reached out to people directly.
Being resilient and overcoming adversity is so often less about “just pushing through” and more about finding clever ways to take uncomfortable action even when you don’t feel like it.
So if you’re feeling resistant to doing the thing you know you should do…
If you’re holding yourself back from taking action that you know you should take…
Ask yourself…
How can I make this fun?
How can I find a way to leverage creativity, competition, or just pure enjoyment to take action despite the discomfort?
Rooting for you,
Jay (encouraging you to make it fun)
