My angst-ridden post yesterday really highlighted to me that my midlife crisis continues: I’m quite successful at what I do and am fairly well-known in my field (an IT specialization), but I think that I’m bored with what I’m doing. This entire contract negotiation process was so indicative of what I waste too much time on with the type of clients that I deal with, and I just want to do something different. Something with a lot less lawyers, accountants and large businesses. Something that makes me feel like I’m making a difference, and doing something productive most days.
Occasionally, I think of my programming days fondly: I could brush up my skills and get back into that although I have always looked down my nose at people who are “still programming” at 45. Maybe I need to lose that snotty attitude and just do it, although it would mean taking an 80% pay cut on an hourly basis, although presumably with a lot less unbillable time spent on bullshit. I know a lot of small businesses that need a better web presence and better internal IT, and could likely help out with a lot of that. Not a lot of money in that, but it would be satisfying in its own way.
I’ve also been spending some time mentoring small businesses, and really enjoy that. I have the sense that I’m helping them to avoid some of the early pitfalls in a startup (having done three myself), and helping them to focus their ideas into a cohesive business plan that they can act upon. Of course, they rarely have any money to spend so are happy to get this advice for free, but wouldn’t pay for it — I wouldn’t have at that point in a startup, even though I understand the value in it now.
Part of me feels like I have one more startup left in me, if I could find the right partners and the right ideas, or even be dropped into a company that needs more experienced leadership at a first-round financing stage. I know my strengths and my limitations in this arena: I’ve been from zero to second-round financing, and I’ve built a company organically (without financing) to 40 people. I had a tremendous amount of fun — and stress — in doing that, and it made me want to go to work each day. I don’t feel like that now.