I asked every AI app what I should do. Then I sat on a video call with my amazing assistant, Jen, asking myself questions while she patiently watched me click around as I attempted to make a decision.
The truth is that beginning again is hard, but not in the ways I’d expected.
Once upon a time, I had a dream to build a really big business, serve people well in a way that created transformation in their lives, earn a lot of money, and retire early.
I did that.
At 43, I decided to scale down my business and see what free time felt like. Freedom 44 was the mantra.
I did that, too.
Around 18 months after shifting my view on life and goals and time and how I wanted to use it, I had an idea, as happens to us chronic entrepreneurial types.
The idea was sparked by the surprising conversations that followed my decision to do significantly less, professionally speaking, than I was capable of.
What I had thought would happen, didn’t. What I never expected did.
I thought I would be kindly asked to leave the entrepreneurship community group I was a paying member of. Instead, the founder took me out for dinner.
I thought I would be the one no one wanted to be seated with at the community dinners. This is one of those dinners where people stand up and say they just published their 10th book, and there’s a copy for everyone to grab on your way out. Or the person who said he’s working to scale his business to $1 billion in revenue.
I stood up and said I was working on my pickleball game (it’s still not good), and that I was scaling down my business, cutting my operating costs by $1M/year, and scaling my revenue to 1/15th of what it had been the previous several years.
What followed was more demand for my time from high-level people than ever before.
I was praised for bravery. I was asked for private calls on the subject. In short, I was applauded. I didn’t think anyone would care. And I didn’t care that no one would care. This was a decision for me, definitely not my ego.
Ultimately, I realized that in the entrepreneurship world— we think the game is to grow, scale, acquire, be acquired, sell IP, get investors, and then exit.
What I didn’t realize was that to build a business you love, make it ridiculously successful by all measures — impact, growth, customer experience, and loyalty, rich in community and reputation, deep team commitment, joy and profitability — to softly close the doors instead of maximizing an exit is seldom done.
Which brings me to this new beginning. I am diving into the idea of courageous pivots. I want to write a book on the topic. As I began hashing out an outline and speaking with potential publishers, I realized that maybe I wanted to do this differently.
Every aspect of every execution of my businesses over the years has had a community aspect. It started with a green smoothie cleanse, coached online via my blog (this was pre-social media and hashtags), and concluded with a global community of certified instructors and graduates of an online cooking school that spanned 80+ countries.
I wondered, what would happen if I did this with community in mind? What if you came along with me as I explored this topic, gathered research, and spoke to people who have done it, are doing it, and/or are guiding others on how to make big life decisions and challenge beliefs.
In starting from the beginning with something new, I also asked myself what starting fresh in 2025 could or should look like? Starting at the beginning, when I am not trying to build something massive, but creating for the art and joy of creation.
Answering this question is what landed me on Substack, starting on a brand new platform, which still feels quiet (like Google Reader in 2009 or Instagram in 2012).
The trailer will be coming later this week. It’s all beginning. Again.
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