20 Lessons from 20 Years: Focus and Is the Juice Worth the Squeeze?
Entrepreneurs are surrounded by seductive ideas. Another side project that might turn into the next big thing. Another initiative to test. Another opportunity that feels too good to ignore. The logic always sounds reasonable. As builders and optimizers, we’re wired to turn time, attention, and momentum into revenue. If something works a little, surely adding more will work a lot.
But there’s a question many entrepreneurs avoid asking until its too late:
Is the juice actually worth the squeeze?
Focus is painful, and that’s precisely why it’s so often avoided. Focus isn’t just discipline or restraint — it’s loss. Every time you commit deeply to one thing, you close the door on dozens of others. Ideas that feel smart, interesting, and full of potential never get explored. For people who thrive on curiosity and momentum, that tradeoff can feel unbearable.
Early success makes this worse. When a business runs smoothly and doesn’t demand every waking hour, the empty space gets filled. More projects. More interests. More responsibilities. On the surface, it looks like balance. In reality, it’s fragmentation.
In my early years of affiliate marketing and online advertising, it was easy to fall into this pattern. A profitable website didn’t need my constant attention, so expansion felt natural. More sites were acquired. Systems were built. New ventures emerged. Outside of work, my time was spent on hobbies, volunteering, organizing events, and (eventually) staying constantly busy. Everything felt productive and meaningful.
Looking back, much of that activity and work wasn’t particularly sophisticated. The core business was simple and highly profitable, but not especially challenging. Diversification and constant motion filled that gap. The busyness masked the fact that the most important thing, that the core business wasn’t being pushed forward with intention.
Eventually, life has a way of forcing a reset.
Business is easy, personal relationships are hard. When external personal disruptions occur, the cracks in an overfilled life become impossible to ignore. Businesses assumed to be on autopilot begin to get quietly neglected. Momentum fades. Numbers slip. And the uncomfortable realization sets in that filling life with “more” leaves no margin for error. There’s no room to absorb shocks, no flexibility to adapt, and no space or time to recover.
When that happens, the instinctive response for many smart entrepreneurs is diversification. When something feels unstable, adding more feels like protection. A new venture related to the core business feels logical and responsible. Its what successful people do, right? Naturally, starting a marketing agency alongside an advertising network made intuitive sense (and I had always wanted to do it). It felt adjacent, complimentary, and sophisticatedly strategic. But it actually did the opposite.
Diversification is distraction by definition.
While it can reduce certain types of risk, it almost always reduces reward. More importantly, it spreads attention thinner and thinner until the original business (the one that made everything else possible in the first place) becomes fragile. Side projects quietly turn into siphons: time, decision-making, hiring, and emotional energy. Once started, they’re difficult to unwind, especially for entrepreneurs wired to chase the next interesting problem and distaste for failure or giving up.
Over time, this pattern compounds with more companies and brands. Acquisitions layered on top of acquisitions. From the outside, it looks impressive. From the inside, it’s unsustainable. Progress slows, stress increases, and focus erodes to putting out fires. Without “more” being part of a plan with personal time available (or the ability to manage teams) the real issue isn’t ambition or work ethic: it’s capacity.
There comes a point when it becomes clear that the problem isn’t a lack of ideas or opportunities. The problem is focus. Or more accurately, the lack of it. What’s needed isn’t another venture, but the simplest, most reliable way to generate income, so that time and energy can be spent on the things that actually matter. Actually living the life that the money affords.
This realization often arrives uncomfortably, suddenly, and when its already too late. Many high-performing entrepreneurs discover they’ve optimized for output at the expense of everything else in their lives. Family, health, hobbies, and personal fulfillment quietly disappear under the weight of “just one more thing.” Unlimited work can, in theory, produce unlimited money. But unlimited money isn’t the same as freedom.
At some point, more becomes excess, and it comes with strings attached that we don’t even see until there’s too many of them. That’s when the teardown begins—and it’s never easy.
Businesses that once felt essential are reevaluated. Ventures tied more to ego or aspiration than reality are unwound. Some projects are let go not because they failed, but because they succeeded in consuming too much attention for too little return. Sadly, its the “fun” ones that often get cut when things have to go. The ones that were launched because it was something you really wanted to do, but when a time crisis hits, those projects are often the least profitable. Creative businesses that require constant involvement prove difficult to scale. Technology plays that depend on deep specialization demand more time or capital than expected. Investments that sounded passive reveal themselves to be anything but when there’s a downturn.
In each case, the lesson is the same: if something can’t be given proper focus, it shouldn’t exist at all.
Letting go is harder than starting. Walking away from upside feels like failure, even when it isn’t. But the lesson here is that prioritization and focus isn’t quitting. It’s choosing sustainability and yourself over accumulation. It’s deciding that what already works for you is worth protecting.
For entrepreneurs there is always another idea to test, another angle to try, another revenue stream possible. The real skill isn’t finding more juice. It’s knowing when to stop squeezing.
And for those who learn that lesson sooner rather than later, the reward isn’t just better businesses. It’s a better life built around them. Focus is probably the most important resource we have.
