At a crossroad, who do I turn to?

I’m a 40+ year old man living in the heart of silicon valley and completely lost on what to do with my life.

I have started five tech companies in the past 15 years and not really had much success except for one which I managed to sell to a friend’s company for a non-trivial amount that gave me a couple of years of time a few years back. Since then, I’ve tried two other startups, managed to build a small team and build great products that didn’t really have a market.

I can code pretty well but not like the ninjas out there. I have done a lot of other things like building compelling pitches, design, business planning, build financial models, legal contracts, etc. So I guess you can call me a generalist.

My issue is that once I go down a path, I tend to spend a lot of time on the minutia, lose the focus on the bigger picture and in some ways avoid getting the product in front of the customers.

At this point I’m about to give up on my current gig and feel completely lost on what to do next. Being in my late 40’s my options are limited and I find myself not capable of competing with my peers who’ve achieved great things and have found a path. Living in the bay area is extremely taxing and leaves me filled with anxiety 24hrs a day. Not sure what kind of counseler I should turn to for help and getting my life back on track 🙁

  • Im turning 40 in few days. Started coding my social network 2 years ago. Its now getting 40k visitors per day. And i think it’s on it’s way to get millions of users. I’m all solo. So you can do it!!!

  • Turning 41 in a few months. Some similarities in our situations (working full time for nearly year & half on what feels like minutia). It was really finding my way. Finding commited people to work with. (I’m not in the bay area). Its my first startup. Like everything in my work, I feel its gotta be ‘right’ before I put it out there. Just getting it in front of select customers. Bootstrapped the whole way.

    Personally, running on fumes. Feel like I should be spending more time finding stability, finding a spouse, starting a family and maybe a day gig so that I can have a big check coming in (that reflects my experience) and I can work with more people part of my day while doing the startup after hours. The isolation of hyperfocus, limited interaction & limited financial reward is very draining. At least for awhile till I get recharged. Havent done it yet.

    Take a look at life coaches. There are therapists that also are life coaches. I think they deal with getting you to figure out whats important and get you on track.

  • Give yourself some time off. The SV rat race can be really overwhelming. There’s always someone that you know personally who just made their millions. One of my best friends just sold his company for 8 figures . ..

    Just know that some of those people aren’t happy either. Sadly, it’s the human condition.

    Get some perspective by helping those less fortunate than you may help. Consider spending time owith children, the elderly, or those that are sick. These people can help take you out of your own problems.

    Best of luck, and remember it’s not as bad as it seems!

    • Thanks! Yes, I’m trying to take time off, but being in the valley makes it really hard to truly get away from the frenzy of startups, investors, exits. You can’t escape this if you’re online.

      As for fining a job, I know I can do a lot but it’s hard to put myself in a box to apply for something due to all the different types of experiences I have and the age factor doesn’t help either.

      I’m very fortunate to have a loving family and my wife is very supportive of my situation, but I need to find peace within by fining a purpose. Helping others is a great way to do it and I’m beginning to help budding entrepreneurs but sometimes that’s even hard to do as the ratio of mentors/advisors to entrepreneurs is skewed.

      I guess I don’t know if I’m depressed and need to see a therapist, or have anxieties and need to see a psychiatrist , or have mid-life crisis and need to see a life-coach 🙂

      • I don’t know that I can relate at all, as I’m relatively young and “green” to all this. But I can imagine what you are going through is pretty taxing, in a myriad of ways.

        I’d say take a vacation, or a day trip. No music, no books, no internet. Unplug, go dark, and just think. Maybe that is to the beach or the mountains or the desert, but just leave everything behind.

        Also, talk to your wife and see what she sees are your strengths, weaknesses and opportunities. My wife keeps me grounded from being too hard on myself and too stupid. 🙂

        • I’d love to connect with you and see if there are any ideas or ways I could help. Make it so we can contact you and I’ll email you via this site (anonymously, of course, to everyone else)

  • I think you answered your main issue in your post you said

    ” build great products that didn’t really have a market.”

    You spent a lot of time concentrating on something that had no market, while that’s sad you learned a LOT in the process I’m sure. So on your next idea, test the market, get opt ins/sales/etc before you go to the trouble of developing it.

    The sheer number of people counting on you to bring something to market should cause you to laser focus on what’s important.

    If that doesn’t help you focus then triage what needs to be done. Look up the Eisenhower Box and use it to whittle away at the time wasters. good luck!

    • Thanks. Eisenhower Box is interesting. I’ll give it a go. I am realizing though that I fall into the same pattern every time and perhaps need serious coaching on behavior modification.

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