On work and freedom

Every morning when I wake up, I feel a slight tingling of dread. Another day has gone by and I’m still where I was the day before (no, I don't mean that I'm surprised I've not been transported somewhere different by my bed). The evening before, just as I’m about to fall asleep my mind will gently nudge me - reminding me that I ought to do something tomorrow so as to move the needle a little. My brain incessantly pings me to do more 'big picture' stuff, to make the most of life, to push myself. Yet all too often tomorrow greets me and I snub the thoughts of the night before. The dread lightly washes over me.

I feel dread because I know I need to start doing something to drive some sort of change but I put it off. I don’t expect things to completely change overnight and I am performing small, iterative changes which will hopefully compound overtime. However, none of those are practically changing my career and life’s trajectory. The things I do daily are divorced from animating meaningful change.

Reading, running, learning new languages, practicing chess, journaling, etc. They all help with a vertical slice somewhere in my life, but not with the big picture stuff. Maybe reading, with the wisdom and ideas shared in books helps, but reading something vs actually doing something based on what you’ve read are two different things.

When I say big picture stuff I mean a purposeful life and career. I’ve not read In Praise of Idleness and Other Essays so maybe I’m missing an important piece- but I feel like I want to be doing more with my time and life. That’s not to say I’m not grateful for what I have, I know how blessed I am. It makes me cringe to say it but this might even be an evolution of gratefulness I’m experiencing: I recognise how unlikely it is for me to be on this beautiful planet right now. The acknowledgement of the brevity of life and wanting to make the most of it.

The problem though is, I am unable to reconcile this feeling with any actionable thing.
I’m not entirely sure what my mind intends when it prods me to do more with my life.

When I reflect on it, awkwardly, I actually want to do less. Less in that I want to be bound to less, free to do what I want. The next thoughts that sprawl out from there are around what I would actually be doing if I was free to do what I want. Yet, I don’t know what that is. And that is a big part of the problem: if I was free to do what I want, what would I do? ¯\_(ツ)_/¯

I am reminded of the cheesy story about the fisherman and the businessman, where tl;dr: a fisherman is pushed by a businessman to turn his fishing business into a massive booming business so that he can spend time doing what he wants. In the end, it is revealed that the fisherman is already doing that by having a chilled job he enjoys, fishing as he pleases. It inadvertently poses the question of whether or not we should inherently derive purpose from our work or if we work to be free to find our purpose.

Regardless of the answer to that question, I don’t know what my fisherman job equivalent is or if I even have one.

I tell myself that I can figure that out later. I convince myself that I can figure out what I want to do once I get to a point where I have the financial and time freedom to pursue whatever I want (and find purpose therein). Which I guess is my answer to the earlier question. So, the next ‘logical’ (I doubt there’s much logic going on here) step is, how do I go about freeing myself?

One option is to work hard at my job, earn money and use my retirement to hopefully find a deeper sense of purpose in the freedom of retirement. But that kinda sucks and is a bit hyperbolic. I tell myself to dial it back a bit and look for compromises.

I have a great job that pays well. There are also plenty of overlaps between the work I do in my job and the things I care about (e.g. working with tech, helping people, making an impact in the world, etc). Perhaps I can find purpose in a regular ol’ job.

However this approach is missing one key component. I’m still not free to do what I want (unlike our fisherman friend). Furthermore, I’m exhausting my best years building something for someone else. I think at this point one might lean two ways:

1. Either be okay with this fact, embrace the overlaps and recognise that we can work for someone else and find lots of purpose and contentment and put the issue to bed.
2. Or, even with the overlaps, selfishly and egotistically desire more independence and freedom.

I’m in the 2nd camp.

If I’m doing something I care about but I’m in an environment where I’m still reporting to stakeholders that aren’t me - well then I don’t really feel like I’m free. I am still ultimately constrained by their wants and needs. Furthermore, there is still an existential underlying issue at play here in that I am fairly certain building something for someone else is more rewarding for them than it is for me.

For some weird human reason, I’m not certain I’ll ever be completely content working on something I have not had a hand in building. I’d even hazard a guess you may well be able to work on something you build yourself or for a company and the end product may well be the same. The journey however, I suspect, would be vastly different.

I reduce it to the fact that I am building their dreams whilst they are the ones living them. And I don’t think it is particularly easy to assimilate or merge into someone else's dream. It is not the authentic you. As Emerson says, “Insist on yourself; never imitate”. This reductionist view is hard for me to mentally overlook. I probably can assimilate if I try, but I fundamentally just don’t want to (I don’t know why).

At this point, I begin to go in circles. Is there a way for me to make money and not be bound to any stakeholders? What might that even be? Perhaps I’ve been to brash and I can find a regular ol’ job I care about working on and that pays well. Do I accept this somewhat watered down path and stop worrying about finding a way to be free to pursue whatever I want, as I’ll sort of be doing that? Painfully, I find my mental gymnastics guiding me back to the same fisherman job idea. This repeats again and again in my head. However, I never conclude the train of thought with being content with doing a regular ol’ job forever. I cannot shake the desire to do/build/create/whatever something of my own bidding.

To do something on and of my own, I need to step out over the ledge and actually do the thing (relatively independently of others). But which ledge? Where do I even step? Modern day creators often say, “do the thing”, “just get started”, etc. I find my brain blanks when it comes to that very first step. I do have a list of ideas and problems I want to solve - yet I don’t feel any of them warrant doing (as they are pretty insignificant problems).

Additionally, if I managed to convince myself that “X” (not the one formerly known as Twitter) was worth building - little by little every so often - I wouldn’t even know how to begin marketing it. How would I get it into people’s hands? And thus I straddle the boundary of my ideas not being worth building and if I do build something, no one will use it anyway.

Recently, though, I’ve started questioning my mentality on this. If I just look at what’s involved and possible outcomes I suspect there is some nefarious motivated reasoning going on.
Am I potentially just convincing myself that there’s no point in starting because I’m just too lazy and scared of failure? Shorterm, the pleasure and peace of not feeling the need to do something more meaningful is lovely, yet subconsciously my mind is unsettled.

When I look at the risks of building something for myself (even just as a side thing), they’re miniscule. What are the downsides, really? And the upsides are potentially fantastic. Which leads me to believe that I’ve gotten comfortable being comfortable and prefer saying, “if only I knew what I wanted” or similar so as to put off actually having to do something. Fortunately, I have become aware of my ability to excuse myself from not doing something, not taking that first step (or second step). This awareness has made me better at squelching those excuses and seeing them for what they really are.

Moreover, I know that part of building something on your own involves learning how to do things unfamiliar to you - like how to bootstrap marketing and get customer feedback quickly. It is part of the journey itself, not a requirement for starting the journey. It makes it interesting and not knowing is not an excuse.

Having reflected on all of this further and revisiting my list of app ideas: a lot of them are actually pretty cool. Real world problems would be getting solved with most of them. I’m quite convinced I’ve mentally watered them down to validate and justify not building them. Should I build any and they were to fail (which is extremely likely in the software world), I would be able to say “eh, it was never a good idea” and fallback into the lazy world of excuses.

And frankly, that’s pretty silly. Part of the reason regular ol’ jobs are appealing is because they offer safety and comfort (to an extent). Someone has overcome that difficult part for us and built a (usually) stable company. I can’t expect that if I am to try to do the same I’m magically exempt for the challenges everyone else has had to overcome when doing the same. I also can’t expect everything to workout perfectly the first time around. Going into it with this prepared mindset protects me from excusing myself out of hard times. Acknowledging it won’t be easy and that it will require hard work (and a splash of luck) from the outset feels wiser than pretending everything will be hunkydory.

The next (and hopefully final) piece of the puzzle is staying motivated and disciplined. How do I ensure, even with all the self-awareness in the world, I actually keep it going about trying to do the thing? I don't think anyone has a foolproof method for this (bar Goggins). It’ll come down to me, remembering all of this (gestures broadly) and that the buck stops with me. I will have to be selective with my time. I will need to keep an eye out for mindless quick dopamine hits (e.g. doom scrolling, reading the news, etc) and for doing something that feels productive (e.g. designing and researching endlessly).

Instead, I will need to put my energy into the thing that tends to feel the most uncomfortable, e.g. doing something productive. I’ve learnt that if I procrastinate when trying to do something, it usually means the ‘something’ is important and worth doing. I will be using this loose heuristic to catch myself and adjust course back to the ‘something’ I’m meant to be doing. I will also be coming back to this specific post regularly so as to keep myself honest. If it isn’t clear from the post, I am able to think my way out of things if it’ll make me more comfortable in the short term. Having a reminder of what I’m after, how fortunate I am to be here, how progress and improvement requires persistence, and so on.

With this, I am going to have a crack at some of the items on my idea list. It’ll only be a side gig but it will be something. And I won’t stop until I’ve given each idea ample effort and energy. And if none of them take off, I’ll have to just formulate new ones and build those. If, at the end of the day nothing takes off at least I can say I tried. Yet I am convinced that persistence pays off and eventually somethings gotta give.