Striking Out

Striking Out

My cousin, Chip, was the baseball player. Me…not so much. I do still have the bats, bag, and equipment that my aunt and uncle convinced my parents to buy when we were kids. I could hit fairly well, but I lacked the coordination for most other aspects of the game. Maybe my boys will show better aptitude. Basically this is a disclaimer for how I may or may not butcher the next series of analogies.

I gave entrepreneurship a shot some years ago, and I struck out. I’ve been pretty good throughout my life at figuring things out on the fly. There was just so much more to figure out than I ever imagined or anticipated. I’m not sure which ran out faster, my savings or my resolve to keep trying. I just remember both were pretty well drained when I returned back to a W-2 some 9 months later. I did not regret the experience; I learned a lot. I nonetheless regarded the experience as a failure. Someone gave me some valuable perspective on what failure had looked like for them. It wasn’t a Struggle Olympics sort of comparison. His intent was to explain that these were not Game-Over outcomes that I had experienced. ?I just didn’t have a successful at-bat. I had simply struck out. The game was not over for me. I would have more chances at-bat. It was the affirmation that I needed at the time.

I’m staring at my next at-bat now. My last time at the plate was not the stuff of Instagram-worthy, entrepreneurship glamorization and vignettes that proliferate social media. I worked harder, longer, and for far less money than at any other point in my career. There was also ugly-crying. A lot, actually.

In no particular order, below are some of the take-aways from that first jaunt that I’ve kept with me:

·?????Beware of over-reliance on past networks

My gravest disappointment came fairly early on. I had hoped that a few of the contractors that had bid the opportunities I had managed for my employer would support me in my own endeavor. All but one declined to help me. What I learned was that they weren’t really MY relationships; they were my employer’s relationships which I was merely managing/facilitating. The work I was trying to cultivate wasn’t in conflict or competition with what I had been doing. I made the mistake of believing that people would value what I had done for them in prior positions and return the favor. I was, unfortunately, over-reliant on that supposition and had to recover fairly quickly from that miscalculation.

·?????Every opportunity isn’t YOUR opportunity

This was a problem of “focus” for me. There are a lot of things that I believe I perform well. However, in light of the first lesson, there was even more work to be done by my own efforts when I was unable to rely on known entities to support opportunities. I cast a wide net, chased a lot of things, but in the end, I didn’t end up landing much. I had the mindset that every day that passed where I didn’t have money coming in the door, I was losing. That was perhaps a bit hyperbolic. At the time, it drove me to chase anything and everything that might help to offset licensing fees and other daily expenses. I wish that I had the presence of mind and discipline to stick to keeping myself open specifically to the things that I ACTUALLY wanted to be doing. And, by definition, it would mean having the courage to decline things that didn’t align with the direction of where I wanted to be heading.

·?????Color outside the lines

Unofficially, matters of ‘compliance’ often have fallen within my area of purview when I’ve been in the employ of others. These considerations are often overlooked during sales and business development cycles; in my experience, it has been us folks in operations (with support from Lega)l to manage and mitigate such risks. When it came to my own thing, I was hyper-focused on trying to secure all of the licenses, permits, and administrative authorizations for anything and everything that I might possibly be poised to do before I even got started. It was costly and time-consuming. I’m not at all certain that the effort was necessary.

The way that many start-ups and even some established companies operate is completely opposite of what I spent my time doing. I can point to numerous times in my own career that I’ve been hastily assigned the task of securing contract requirements AFTER the deal has been done. In my effort to “be better”, I over-rotated. There’s probably a middle ground that would have been more appropriate. Secure the things needed for the core pursuit(s). And if there is an opportunity just off on a tangent that’s still related to what you want to do, maybe worry about squaring away those sorts of details once you’ve landed the thing. In my case, no one was paying me (or reimbursing me) for those expenses. It would have been far better if I could have built in the cost of those things into a secured contract to recoup those expenses.

I’m not saying, “Become a scofflaw!” I just think I could have gotten further and had more cash on hand if I wasn’t so pre-occupied with checking every box. It seems like the big fish either dare to get caught or otherwise calculate that the rewards outweigh the risk. I’ll never misstate or misrepresent my standing in any situation, but I might not be quite so fastidious about all the minutiae until truly applicable and necessary.

·?????Ask for the business/Count yourself ‘In’

I was not aggressive enough in stating my intent and/or asking for the business. There are a few of us high school classmates that are active in residential real estate. One of our classmates, a few years ago, hired an agent that wasn’t any one of us. These things often come down to personal preference, comfort, etc; so, I wasn’t taken aback by the decision. I just remember at one point she shared that she had clearly gone through a life change which signaled that she would be in need of real estate services, but none of us had asked her for her business. I never want to swoop in like some credentialed vulture when such things occur, but the flip side of that is perhaps a more majestic bird, like an eagle, is what people are counting on us to be in those moments. I had not yet had that mindset shift though.

There were other instances specifically applicable to my first launch where I counted myself out. I had familiarity and training in a certain thing, but I didn’t have any solo experience doing said thing as a part of this business. Although I had the problem of “focus” and was trying a bit of anything and everything, a big reason for this was because I had counted myself out of the specific things that I ACTUALLY wanted to be doing. I ended up spending too much time going after things that I felt qualified to do but not necessarily driven to do. I believe I would have been better served channeling all of my effort into relentlessly pursuing what I want out of life. Even if I were to fail again, at least it would have meant that I was on mission, learning and experiencing things along my chosen path (as opposed to merely being a victim of chance and circumstance).

Again, I’m not good at baseball. But I think there are more at-bats awaiting us when we’re ready to try again.