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Thanks for this. I think my current feeling is definitely a bit "grass is greener", and I'm overestimating how much help a larger company structure would provide. But I can't help thinking: running a company requires about nine different skill-sets/areas of expertise, and who has all those? If the job also involves time spent deep-diving into particular work (and literature is even more absorbing than coding), I don't see how one individual could balance the two.

But it's nice to see someone (presumably at a similar stage of life) heading in my direction from the other side. :)

I got a business coach, and took a small business course which connected me with other small businesses in my area. It was an invaluable lesson.

I was forced to read the book "E-Myth Revisited"[0] as my course material. It gave me incredible insight into delegating and many of the fundamental issues with running a small business.

Without my accountant and a few key, incredibly supportive clients, my business would have gone under a long time ago.

My business coach had started and sold a number of businesses, and was able to advise me on things that I would never have done on my own. Look for someone like this in your life, even if only temporarily.

My wife started helping with some aspects of the business as well, and I couldn't do it without her. You need help, period. I've trained 2 of my kids to build websites, one has moved on to college in some other industry and the other is interning at a bigger company (building websites). And I plan to teach my other kids as well, and have them help where possible.

What this taught me was that I can't do everything myself, and I don't want to anymore, it just sucks to do it on your own.

The best thing that happened recently is making friends with another local business owner, who also builds websites, but our business interests don't conflict, and we respect the others perspective a lot, so we get to hang out from time to time just to talk and have coffee. We understand the world in a way most others cannot. The struggle, the freedom and preasure, etc..

Keep looking for answers to your specific problems before giving up on your business.

[0] https://www.amazon.com/-Myth-Revisited-Small-Businesses-Abou...


You have to “cheat”. Cheating is when you build your side project/business while employed. Some can arrange this but many simply can’t. I chose to quit a lucrative, somewhat stable consulting gig and with reliance on savings to start an independent software provider service in the same field. Boy did I learn about the same skills shortage spoken about in this thread and the article! The emotional rollercoaster point is so true. If you cannot regulate your emotions (basically become a stoic), it will hurt no end.

It’s been 5 years since I started and I have only managed one enterprise sale (that sale itself took me two years to sign). Been hobbling along in zero growth purgatory since. If this client cancels I am fucked.

It is easier to imagine a life of zero responsibility and drastically reduced stress and anxiety. It’s a fantasy for me now imagining myself “cruising” (another poster’s word) at a full time job. I am 45 now and jokingly imagine myself unemployable. I wouldn’t last a day being microanaged.

My autonomy is important to me. My autonomy gives me full control over how I develop my craft on my own schedule.

When asked by people how things are going, it’s always “fine! Great! All good!” (But the ruse is only as thin or thick as my skin)!

> I am 45 now and jokingly imagine myself unemployable.

You are not, far from it. Running your own business has taught you many lessons which will come very handy when looking for a job. At least that's my experience.

> Running your own business has taught you many lessons which will come very handy when looking for a job.

I imagine it's very dependent on what you do, what your skills are, and what type of industry you're in (and, finally, who is interviewing you). I've done my own software dev/consulting for a decade now and am possibly unemployable (or, at least, for most positions). "Standard" dev jobs - I've interviewed for some, and may be intimidating to some (and yeah, I realize this may be a full-of-shit self-aggrandizement view of myself too). For a decade, when coming in to a project, I'm typically given a wide range of access to multiple people, and a wide variety of information, to help make the best decisions possible. I've interviewed for "development jobs", and the environments are typically the opposite - info lockdown, do the assigned tasks, etc.

I've been in those situations, and watched as companies go under because of bad decisions, and can't easily deal with not having more info access to understand the decisions/directions (even if I don't agree with them, seeing the bigger picture can help me accept, or... start to look elsewhere).

So... yeah, the GP (and myself) may not be completely unemployable, but the sorts of 'jobs' where someone wants the sort of experience someone has running their own business... they aren't as plentiful, and often don't get advertised (and likely aren't going to be the sort of thing body-shop recruiters are going to be reaching out to you about). (and age is no doubt a factor as well - I'm north of 40 and think 'employability' is thinner than it was for me 15 years ago).

I agree that being employed as a regular developer gets harder and harder with age and with experience outside of dev world, but at the same time you are getting better and better at positions which require more business skills, like team lead (if your tech skills are still good enough) / product manager / CTO / tech cofounder / ... There are many companies that don't know they need this kind of person, and it might be difficult to find a match. But once you're in, you can make a huge difference with this skill set.

> There are many companies that don't know they need this kind of person, and it might be difficult to find a match.

that sounds like a different angle of saying what I was saying. if a company doesn't know they have a need for what my skills are, i'm less likely to employed by them. if the majority of companies in an area also don't know they have a need for my skills, i'm less employable (or perhaps unemployable) in a particular area.

i've gotten way too good at seeing roadblocks well before other people do, and the roadblocks are almost always nontechnical. This can be taken as 'having a negative attitude', but it's just pragmatism born out of experience (yes, understood, my delivery/tone may play a part in this, but sometimes I'm just the guy saying something that someone above me doesn't want to hear). As an external consultant, you're brought in to be able to say those hard things that people perhaps can't say for themselves. As an employee... you're potentially "toxic".

Echoing this myself. I swore off having a boss again after my last (also only) position in an agency. After six years sometimes I look at those 180k remote jobs with a wistful eye. But the chance of getting to that point with a company I built.. That feeling makes wearing all those hats and all those laste nights worth it.

Maybe you simply need a change of work. Nothing wrong with that. You could weigh the pros and cons until the cows come home, but that doesn't change the fact that a change is welcome.

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