I was wondering if anyone else has gone down this same path... and if so, if you have any advice for me regarding this career change?
Yes, I went down that path. My advice is to consider very carefully whether you want to move away from doing something where you can say, "I make great money and I love what i do," and into something you've never done before: run a company.
Being an early-stage entrepreneur is different from running a going business, and both of those are really different from teaching and programming. The talents, skills, knowledge, and wisdom required for success at each of those is really different, and you can be good at any of those and be a dismal failure at the others.
Here are a few questions to ponder:
- Do you have a business plan? If not, why not? If so, what does your analysis tell you about your prospects? Have you had it reviewed by competent outsiders, and if so, what did they say?
- Who is going to do your books? If it will be you, do you know what you're doing, and how much of your time will it take away from things you enjoy more? If it will be somebody else, will you have an accountant audit them?
- Who is going to do your marketing? Your sales? Do you know the difference? Again, if it will be you, do you know what you're doing, and how much of your time will it take away from things you enjoy more?
- If you have too much work to do, will you bring on programmers or non-programmers? Will they be temps, contractors, or employees? What will you do when (not if) they screw up? How tolerant are you of people not doing things the way you'd prefer?
- Do you know how to determine how much value an individual you bring into the company adds to it? Can you determine how much they cost you, in terms of pay, overhead, management time, etc.? What will you do if someone isn't breaking even, and how long will you give them to become profitable? Can you bring yourself to terminate someone even if you like them? Even if they have family members they're supporting? Do you know the criteria and effects on your business for firing versus layoffs?
- How will you handle things when running the business takes up so much of your time, you don't get to program?
- If you bring on other programmers, will they be as senior as you? If they will, how will you afford them? If they're more junior, will you be happy to take a lot of your time to mentor them, and spend a lot of your other time doing the really nasty code they're not capable of doing right?
- If there's a downturn in your business, what will you do? If it's a choice between your business failing and putting people out of work who you like and are doing a perfectly good job, what will you do, and how will you feel about yourself?
I would really suggest that before you make the leap, find some successful businesses in the same general area (not direct competitors) and size range you expect to be at in a few years, and either go talk to the owners about what their lives are like, or ideally go work there for a few months and see how things are done. Then think really, really hard about whether, and how, you want to have a company.
When I made that same move from freelancing to a business back in the early '90s, I didn't consider any of these questions, and just went blindly ahead. It was one of the worst decisions I ever made. Despite what I wanted to think, just because I was smart didn't mean I had what it took to run a successful business. I have neither talent, nor skills, nor drive to manage people well or run a company effectively - it's just not my personality type - and the more I tried to force myself to do it, the more I resented what I was doing. When the company collapsed several years later during the depths of the dot-com crash, I had to throw a lot of fine people out of work, and felt like a piece of s--t.
Afterward, I went back to freelancing, and have made way more money than I ever did with the company and been way happier. You couldn't offer me enough to run another company. My wife and I might wind up selling some software through something like the Apple or iOS App Stores, but I regard anything that could involve being responsible for managing other people or making payroll with unmitigated horror.
