Having reached an unexpected and somewhat anticlimactic place in my life, I’ve decided to allow life to simply “happen” and to stop forcing it. Let me explain.

As a long-time “successful” entrepreneur, I always had some viable business project in motion. At one point, I felt like I could do no wrong, finding success in virtually every business venture I undertook. I had two lucrative exits from startups I co-founded, among other successes. Money was never an issue—I just made more.

Now, as I race into my 50s, the tides have turned. I’ve been humbled by a few neutral or outright business failures. I’ve lost money and time. More importantly, I’ve lost confidence. Mistakes have made me introspective, and while I know better, I’m hard on myself. Our brains love to dwell on self-proclaimed “problems,” and I find myself focusing on failures more than the goodness in my life. Objectively, I know we can’t win them all but but it’s hard to keep that focus.

Recently, I’ve even applied for a couple of jobs—coming close but not getting either. Mentally, I chalk these up as more losses. So, what’s happened? Where is my mojo?

A Hard Truth: You Can’t Force Life

All this reflection has led me to a realization, and hence, this blog entry! Just like you can’t fit a square peg in a round hole, you can’t force certain things in life. While we may feel pressured to work, earn money, or conform to societal expectations (what we ‘should’ be doing at various points in our lives), sometimes life has other plans for us. The key is recognizing when to let go and trust the process.

But what are those plans? How do we figure them out?

The epiphany I’ve had is this: Life unfolds the way it’s supposed to when you let it flow and stop forcing outcomes.  Or, at least I’m actively testing this theory which seems to be quite logical.

A Natural Flow: Lessons from Dating

Just like finding a life partner, the best things tend to happen when you least expect them. When you focus on what makes you happy—activities that bring you joy—you naturally attract the right people and opportunities. I’ve shared this advice with peers struggling to find a spouse and I actually applied it my life and have been happily married for 10-years. Often, frustration stems from trying too hard, which creates pressure and disappointment. Hence the thesis:  When we let go and immerse in fulfilling activities, focusing on happiness more broadly, things usually fall into place naturally.

Human nature drives us to chase after what we want. And while that’s productive in many cases, it can backfire in areas like dating—or, as I’ve realized, in other aspects of life.

Applying the Same Lesson to My Life

Because I’m not working right now and haven’t had recent business successes, I feel uneasy. I see my peers being very successful and seemingly happy – which adds pressure.  That uneasiness drives me to try even harder, which only seems to make things worse. So, I’ve decided to take my own advice: I’ll stop chasing after business opportunities & jobs (they’re overrated anyway!) and instead focus on hobbies, interests, and personally enriching activities.

I’m relinquishing control—for a little while—and trusting that, during this period, I’ll gain experiences, skills, friends, and inspiration that will guide me to my next professional chapter. Importantly, I’m aiming to find contentment and ease along the way.

A Year of Growth: Sailing, Cooking, and Letting Go

I’ve always been interested in sailing and cooking and want to get better at both. Why not devote the next year to pursuing these passions? I can do this in a productive, cost-effective way, even on a tighter budget. By the end of the year, I’ll be more skilled, more experienced, and my life will be richer for it.  That’s almost a certainty.  

Concurrently, I’ll embrace the idea of relinquishing control. Trusting the process, I believe the rewards—whether they’re new skills, friends, or fresh inspiration—will outweigh the uncertainty of this period. And at the very least, I’ll be eating more tasty home-cooked meals this time next year!

Does this resonate with you in a similar way?  Please share.  I’ll be sure to report back on how this journey unfolds and if the winds were favorable.