The other day at work, we were talking a little bit about the kinds of work we go after. In the business of making software, it's interesting that we have all three major flavors of work: Working for The Man, self-employment and entrepreneurship. Various forms of these categories are often glorified as the ultimate thing, but I don't think there are any clear winners or losers among them. Your personality, interests and life in general have a lot to do with what works and what doesn't. (See what I did there?)
Working for The Man gets kind of a bad wrap in certain professions for some reasons, because of some implied servitude or something. Working for a company comes with a lot of wins, not the least of which is that you aren't likely putting your own money at risk to conduct business. As long as the company is stable and you're adding value, there's a good chance that you'll be in a good place. If the company culture is particularly awesome, you'll get to collaborate with great people and be a part of something interesting.
On the flip side, it's not uncommon to work with people who add very little value and fly under the radar, maybe for years. They might lose the ability to innovate and improve on their work. They're free to make a radical shift and suddenly decide they don't need you anymore. In some places, it might be difficult to have any impact at all that you feel good about. And of course, the big corporate culture of constant promotion is not for everyone.
Self-employment, which is different from being a true entrepreneur, can give you a great deal of flexibility. It's the kind of role where you may augment full-time staff, or be a consultant. Depending on the arrangement, it's very possible that you have extreme flexibility in when and where you work. You can choose the interesting work and let the uninteresting stuff go to others.
This has it's drawbacks as well, not the least of which is that you're always on the lookout for the next thing. In good times, it's not a big deal, but when the economy isn't great, it will seriously wear on you. You're also not really a lasting part of anything, which may or may not matter to you.
Being an entrepreneur is often regarded as the ultimate job. You start a company, and you build it. You choose the people you work with, and you bring something to market. You get to be the boss, and you make the rules.
This is obviously the most risky work mode. You might be able to set your own hours, but you have to work your ass off to make things happen, especially early on. People depend on you to do things right, because you also sign their checks.
I've spent all of my professional life in the first and second scenarios, and I've experienced all of the pros and cons. While I do have my own business, it's certainly not "stay home money," it's just a hobby. It's crazy that each of these situations can get you out of bed in the morning, and the same situations can make you want to never get up. As much as we want to decouple our sense of self from work, the truth is that we want to be vested in what we do, to connect to it. When those businesses fail, or contracts end, it doesn't feel good at all if we were into the gig. Jobs can be like relationships in that sense.
One of my former coworkers just set out on his own a few months ago, and I give him all of the credit in the world. He left a really good thing that I'm enjoying a great deal. But it reinforces my point, that there is no perfect way to work. It just depends on your life situation.
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