Ask HN: How Do I Start Over?

[fisherjeff]

Ten-ish years ago, I co-founded an unexpectedly successful business. But I’m running out of energy to give to it, and really to software engineering in general, and am starting to think about what’s next.

I’m more financially secure than I could’ve hoped, my business is in good hands, and I think the timing will be right whenever I’m ready to leave. It turns out, though, that I just have no idea how to even start thinking about a second career.

Anyone have any tips?

[MilnerRoute]

I think it's hard for people in general to think differently and admit to themselves what they really want to do.

I had a friend who decided: they didn't want to work at all. They moved someplace cheap, worked the bare minimum to survive, and then enjoyed having free time. Travelling, exploring the world... That is an option.

I hear stories about people who take an off year and work at an Amazon warehouse or a local fast food joint. Maybe they become a local tour guide, welcoming people to their town. Getting a low-paying position doing meaningful social work. Starting a side hustle selling old comic books or a certain kind of antique or artwork that they have a special expertise in.

If you're having trouble getting to this kind of "outside the box" thinking, maybe a good place to start would be...talking to people. The book "What Color is Your Parachute" got a lot of good publicity for it's basic insight that "information interviewing" is a great way to explore fields you're interested in. But the other take-away from that is there are a lot of things in the world that we just have not heard about yet -- ways to make money, ways to spend time. And you'll never know they exist until you do some research -- some talking to people.

[fisherjeff → MilnerRoute]

> I think it's hard for people in general to think differently and admit to themselves what they really want to do.

Yes, exactly. And not to mention it’s something that takes real effort and time, which can be in very short supply.

[liberia]

Do something that gives you energy both mentally and physically instead of something that saps your energy and leaves you drained. What’s your social media engagement look like? The two most important days of someone’s life is when they were born and the day they find out why.

[fisherjeff → liberia]

My work actually does energize me; the problem is that I tend to overspend my energy budget, so, on net, most things end up an energy sink. That was fine(?) 20 years ago but just not sustainable anymore.

[liberia → fisherjeff]

For me, I stopped being rigid. That takes courage to get out of a comfort zone. Try something totally oblique to what you’re used to doing. Recognize your strengths and build on top of them. (For me one of my strengths is curation and organizing information). You can only build on strength. Hope this helps.

[fisherjeff → liberia]

It’s funny, I had the same realization about running a business like 5 years ago: If you’re too rigid, everything becomes a Big Deal and needs addressing and there goes all your energy. Hadn’t made the connection to my current situation, so thank you for that.