It is easy to see the beginnings of things, and harder to see the ends.Joan Didion
Have you ever sat at your computer after a string of failures and nearly given up? That event is reminiscent of every ending to a project I’ve had over the last couple of years. As detailed in my other post, it follows the same cycle of excessive hype, failing to achieve milestones and regret towards the end.
Many wide-eyed entrepreneurs hope to stamp their difference on the world while making a buck but most of them fail. I’m no different. My string of failures discouraged me and emboldened me, ripened my skills but also stretched them thin. You spend so much time trying to breakthrough that you don’t know what to do when you actually get there.
My first taste of success came when my last startup was acquired in late 2020. I spent years working towards that goal and the final moment tasted bittersweet. It reminded me about how much luck mattered in this game outside of good old hard work.
I rejoiced at the buy offer. It was payoff for all those years of hard labor that culminated to this moment. I lamented through projects without much success, wiping my brow with each fail and dusting my slacks to get back to work. I scribbled my name on the offer and let out a sigh of relief. I could finally breathe again.
Most entrepreneurs can’t function without something else cooking. A week after the acquisition, I grabbed my whiteboard and decided it was time to construct another project. But I struggled. I feigned ignorance at first — I needed more time off perhaps. Yet I was shell shocked every time I came back to that whiteboard. My markers would sit motionless while I stared at a pristine board. My creative juices had been squeezed dry.
It was time to reassess the situation. I likened it to my writing process — anytime I write an essay, I’ll leave it for a few days and come back to it with a fresh perspective. Writing with continuous fervor serves its purpose for habit building but can have detrimental effects when developing a story. Breaks are important for approaching the piece with unique ideas under a fire of saccade. I decided to use the same principles for my startup journey and promptly closed my dozen stale startup Chrome tabs and went out for a walk.
Loosening the grip was unnerving at first. Startup discussions were my bread and butter as I enjoyed the atmosphere and learned quite a bit from them. Once I created some distance, I neglected meetings and focused on other areas of my life. Podcasts, forums and chat groups weren’t as appealing to me anymore because I didn’t share in the same vision like I used to.
But every unseen session served as a reminder for the opportunities I was missing. I wanted to build a new startup that would run long term as a self-sufficient business. It would be my full time focus and make a positive impact. Although the break was good for my health, it was still in conflict with my larger goal. It created anxiety. Every new episode and every new book release would worry my conscience. What if this piece of information could be the missing link I need?
I moved on by relegating the thoughts. My entertainment news discussion declined in tandem with my social medias (the Twitters and the likes). The cogs that kept my life in sync with the startup world began to drift apart. It was like I was operating on a rhythm independent from all the bustle around me. I read less business books and spent less time worrying about missed opportunities.
Much of the other parts of my life were shoved back into the spotlight. It makes sense, time freed needs to be spent somewhere. I picked up new hobbies and committed myself to a few new goals to ease my mind. I Googled “cheap hobbies” and writing was one of the most recommended hobbies to pick up. Hey, I was good with a keyboard so this would be a perfect fit.
The litany of domain names I hoarded started approaching their expiration dates. One by one, each fell into the grace period and then silently expired. It felt blissful. No longer did I spend money to maintain projects that I might one day work on. The last dot-com drop was the impetus for restarting my startup journey. It renewed my focus on a select set of projects that I could work on at a time.
Here are some things to consider if you’re on the fence for taking a break:
A break doesn’t have to be an entire year. It can be as short as a few days to a week. Different people have different needs for regeneration. You might be surprised on how short of a break you really need.
Gain fresh perspective on what you’ve been doing. Just as coming back to edit a piece you wrote, distancing yourself for a bit gives you room to breathe and do other things with your time.
Bring focus back into the picture. You can harness that renewed perspective to analyze what you’ve been doing and how to proceed differently (if needed).
Taking a break was therapeutic. It gave me a renewed sense of purpose and focus on the projects that matter to me. It’s like starting over from a blank slate. I discovered that the very act of creating is what I enjoy the most. It gave a better understanding of what my strategy and vision would be in the following years.