Do You Need an End Game?

I quit my job in March of 2015 and started working for myself as a freelance marketing consultant. That’s relevant to my overall point, but so are the events leading up to that decision. I’ve been a “top performer” at every place I’ve worked, but not out of ambition. Just because I find most jobs easy. This has lead me into an unpleasant cycle. I do well at my job, and it becomes too easy or repetitive. I get promoted to some middle management position, which ends up being more responsibility but little power to change things I care about changing. This makes the job worse. I have no desire to either stick that out nor keep moving up the ladder, so I quit.

That lead me to my last job. I went in with the hopes of changing that pattern. I took a position that was a demotion, but it was sold as one where I could really focus on things I cared about. Improving process and “innovating” (that’s become one of many dreaded words for me, as it generally just means taking some existing process and both simplifying it but also prettying it up so it can be sold to customers at a higher cost and also higher margin. You’re not actually creating anything new. It’s like Kraft taking the actual cheese out of Mac N Cheese but adding more “cheese flavor” to save money but then selling it as “new & improved”. Anyway…) was a big part of the recruiting pitch. It turned out to be an even bigger oversell than I typically plan for, but still, I hoped I could just be comfortable for a while. But as it goes, companies want to keep growing and as new business came in the typical decision was “Well Jay is one of our best people, let’s give this to him.” And not only was I doing work I didn’t like, but an increasing amount of it. The 60 hour work week became something to aspire to. And it came to a point of either forcing a change or quitting… so I went the former and again found myself in middle management via a newly created role. Worse yet, it was management of a department I didn’t want to be a part of but had to oversee because of lack of easy alternatives and politics.

Whatever though, the point is not to gripe too much. Back to the point. After a short while of the typical misery of this new position, all the same problems I had in the past with doing work I really had no desire to do (managing people, being responsible for budgets, having to oversee the day-to-day minutia instead of my strengths which are bigger picture planning & problem solving), I came to that same crossroads. This time I thought, what if I were to keep pursuing career growth? I was working for a company of like 400 people, but in my division it was much smaller. I could see the people above me vacating in the near future for one reason or another. It would be possible to get to a VP level or whatever they were calling execs at the time. That wasn’t necessarily something I desired, but probably just hoping for greener pastures. But also some strange confluence of circumstance seemed to make me feel like it was something I should want to pursue. Like maybe this middle point in the totem pole was a necessary step and the goal should be to overcome it and climb higher. I don’t know why I felt that way, but I think if anything it was because there seemed to be no alternative. Telling a company “I’m happy where I am” makes you look like you’re unmotivated or not a team player, likely a flight risk. And staying at the grunt level meant that in most companies I’m just going to take on more and more work and get the biggest problems to sort out. So maybe there is no choice but to keep moving up?

That desire was put to a quick end when the company got acquired. Suddenly I was part of a public company and had maybe six levels of management above me. I really had no way of knowing, there was no org chart I ever saw and it seemed to change rapidly anyway. But even so, I was more valuable as a resource for doing work in this new company rather than a rising leader or anything like that. Once the dust started to settle and I was relatively certain my job would be safe and also stagnant, I quit.

That leads me to the present, and closer to making my point (which is supposed to be about music, but I suppose also life in general). Because of dumb luck in making friends with the right people, more dumb luck in timing based on general demand for what I do, my experience/talent, etc., my freelancing life has been a success. My hope was to work 20-30 hours a week and make at least what I did at my previous full time job, leaving life in general unchanged but giving me a mental reprieve from long hours of working and the ability to pursue more hobbies. I landed a big client that would’ve allowed for that by themselves. But it seemed risky. More risky than the typical fears that come from having all your income from one client. Long story there, but point is that as people came to me with referrals and whatnot, I said yes to plenty of them. And suddenly I was working more than full time again. I got sub-contractors involved, formed a legal business, kept growing. Within seemingly no time, I have people coming to me pressuring me to grow more. I have people who want to be employees. I have people who want to be partners with equity in my business. And just like before, I find myself thinking, maybe this is the only way. Maybe I have to find a way to not just be a freelancer, but grow, have employees, have an office, etc.

While this has been taking place, one of my few escapes has been music. I started getting together with a good friend that I’ve played music with on/off since high school. We drink beers and play obscure cover songs. It’s still work to make time in the schedule and learn the songs and whatever else, but it’s worth it. It gets me out of the house (when you work from home, even if you have an office that is supposed to be your work space, you’re not going to trick yourself into thinking you’re “leaving for work” every morning. You’re just home, all the time. And even in non-work time, you still feel like you’re at work. It’s maddening, but there aren’t great alternatives, at least where I live), it provides some non-work social interaction. It’s an escape, literally and figuratively.

But then it started happening… See, I play guitar, my friend does as well and he sings. And we’ll play a song and think, “this would sound so much better with drums.” And we’ll talk about days gone by when we’d play shows live here and there. Many of those experiences were horrible, but some were great. Most of the horrible experiences were because we got in over our heads and were the headliner or even the only band playing a given night, and we were never deserving of that, so the crowds were bare and it wasn’t fun. But anyway, we’d talk about the good shows and how it would be great if we could just be the first opener of the night, play our cover songs, watch the bands after us, mostly rely on them to bring the crowd.

Suddenly we find ourselves a drummer. And a bassist. We even think about finding someone as a dedicated singer. And people are talking about maybe we should do some originals. To everyone involved except me, it’s likely harmless thoughts. None of us have any desire to make more of this than it is. We’re past the age when you can “make it” as musicians and all pretty realistic about whether that could ever have been possible for us anyway. But still, my mind immediately jumps to my working life. I think, we’re going to play covers, and then slip in some originals, and then more and more. And that’s going to make it easier to get shows (because popular local bands don’t typically want to play with cover bands). That will keep growing, and suddenly we’ll be the headliner at some club that’s way too big for us and we won’t be able to draw a crowd and it will absolutely suck again. That’s not even getting into the growing time commitments, yadda yadda yadda (it’s hard enough to get together once a week to practice, especially since I have to sacrifice work or whatever else to practice and learn things on my own, then put aside more time to practice as a group).

Again, I think for everyone else in the group, none of this is even a consideration. At least not the panic that comes with it for me. But it seems to be in the back of all of our minds. You get good at something and there’s various internal and external pressures to expand. Be it playing more shows, bigger shows, recording an album, playing outside your immediate geographic area, and so on. Or in the earlier part of this post, moving up in your company, forming a proper business, whatever. We’re all conditioned to keep chasing growth. We’re told that if you don’t do that, there’s almost something wrong with you. I don’t even say this in the demeaning “someone has to dig ditches” sense that speaksĀ limits on personal achievement for some people, but in the sense that wasted potential is seen as a cancer. We’d rather overshoot our abilities or comfort level and fail miserably rather than be seen as not squeezing out every ounce of potential we have. And that really sucks. I don’t know if I could do my job as a freelancer for the rest of my life and be happy, but if I were able to make a good living working 30 or less hours a week I know I’d be happier than I’ve been in any other job I’ve had. Is it a bad thing that I’m prioritizing personal interests and friends/family over work? And with music, if we’re able to play songs we like, get some shows here and there, not argue over the writing process, not have to put in tons of time/money to promote shows, and just stay at that point for as long as it’s still interesting, what’s the problem?

I think for any pursuit to which we dedicate time or money, there’s an expectation we have an end game. A destination we’re shooting for. I got asked that plenty while trying to find a drummer and bassist, whether we wanted to write songs, record, tour, whatever. And I think things would be a lot easier and flat out better if that weren’t part of the equation. This isn’t a life or death scenario and it’s not even close. There’s little consequence in focusing on the immediate. Just think, am I happy today? If yes, stay where you are and try not to change. If that turns to a no at any point, think about whether anything can or should change, but not until then. If you’re not happy where you are, why do you think taking on more responsibility to pursue growth is going to fix that? And if you are happy, why the hell would you risk that? If you look at things in those terms, it seems less like a lack of ambition to me. If anything, it’s far more ambitious to always pursue comfort and happiness rather than chase toward some destination you may never reach. At least when it’s a destination you’re not sure you even want to reach.