I'm 37M, grew up poor in a third-world country. The kind of poor where you ate every single rice grain in the bowl and bicycles were considered luxury for kids. I studied like hell, got a scholarship, and made it to North America. It felt like life finally gave me a shot.

I spent my 20s and early 30s grinding through the startup world. I built a company from nothing as the CTO. We sold it a couple of years ago. It was a decent exit, enough to feel proud, but nowhere near life-changing. Honestly, a lot of people I knew who just bought a house in the right city at the right time made more than I did.

After the sale, I put half into ETFs and used the other half to try building again. I toyed with ideas, recruited teams, explored directions… but nothing stuck. The past 2 years have been a mix of hope, stress, and quietly pretending I "have it together."

I don't. The economy sucks. AI is sucking up all the investment money out there. I'm burning through savings. Couldn't raise money. And now I'm looking at my accounts and realizing that I'll need to get a job very soon.

Here's the part that scares me: I have no idea what job I can even get. My experience is so startup-specific. Strategy. Vision. Product direction. Hiring. Fundraising. Technical enough to lead teams, but not the deep hands-on expertise companies want in interviews. And I haven't done whiteboard interviews or LeetCode stuff in ages. Honestly, I'm embarrassed at how rusty I've gotten.

I'm scared. Like actual fear. Fear of interviews, rejection. Fear that I peaked years ago, that maybe I wasn't as good as I thought. Fear that I'll disappoint everyone who believed in me and the kid I used to be, the one who clawed his way out of poverty through strength and determination to make it somewhere.

Those over 30 who've gone through career reinvention, layoffs, failed ventures… or anyone who's had to start over after thinking they "made it":

How did you handle the fear?

How did you figure out what roles you were actually qualified for?

How did you approach interviews after years away from them?

Is it normal to feel this lost at this age?

I'm not looking for sympathy. I just need perspective. Maybe advice from strangers who've been here.

Thanks for reading.


19 comments

  1. You are in for a job in technical sales, or even director of sales at an IT place.

    But, there are some job boards that are hyper specific to startups, I’m sure you’ve used them before if you were on the other side. Try applying there. A Chief of Staff / #2 type role wouldn’t be bad either.

    Without pensions, everyone goes through job change, and reinvention, and most everyone is at least a little afraid of the unknown unknown. Just prep, and when you think you are prepped, prep some more.

    If you do end up interviewing for jobs, be sure you don’t feel like you are losing a job because YOU didn’t prep enough.

  4. Hang in there. It’s a tough spot to be in but you can climb out of it.

    You have the rather typical jack of all trades skillset from building startups. Sales would be a good fit, so is PM IMO.

    If you have other startup founders in your network, talk to them. I think 30-50-person startups are the sweet spot: big enough to have some sense of stability, small enough that they are flexible about roles and the founders would just hire you for your skillset/experience, not to force you into a job description.

  5. I started 30 as the CTO’s right hand man, before I was 31 the CTO was axed by the rest of the execs and I was collateral. Was a pretty rough time. I had a good network but the asks at places I was interested in joining were for deep experience in specific areas. I had a few good interviews that went nowhere, and a lot of bad ones where my dislike of leetcode caught up to me. But I kept doing it, and eventually found a great niche at a non-tech company that wanted to do some custom internal development while the company overall has had some rough points my org seems to be weathering the storms pretty well.

    Given your experience I’d focus on finding places that want similar things that don’t require enterprise features, or looking for new ventures in your network and become the first name people think of when they think of doing early product work.

  6. I’m 39 and run a creative agency for startups.

    I talk to a LOT of founders.

    You guys always set ridiculous goals and beat yourself up harshly.

    2023 was my worst year ever in business.

    I coasted through lockdown as it was so easy to win business.

    Then we hit a crunch, funding dried up and startups tightened their belts.

    I just worked ridiculous hours through 2023 to do great work and build case studies.

    2024 was my best year even (with long hours) and 2025 has been similiar revenue (with a much better work/life balance).

    You can always create new opportunities when you dig deep.

    I’ve had a MASSIVE positive shift in my mental health over the last two years.

    I decided to be relentlessly optimistic, no matter my external circumstances.

    I’ve unlocked so many incredible opportunities.

  8. > My experience is so startup-specific. Strategy. Vision. Product direction. Hiring. Fundraising. Technical enough to lead teams, but not the deep hands-on expertise companies want in interviews.

    You’re a bit at the crossroads in where you want to go. You can grind leetcode and gain more technical knowledge, or you can go more towards the leadership/management route.

    Don’t sell yourself short, all that knowledge you gained running a startup wasn’t for nothing. That’s valuable skills and experience that some companies need.

  9. Not quite the same as you but for 20 years I had worked freelance, enough that I could work from my home office. That all changed with COVID. None of my clients were doing business during lockdown. I found myself looking for work during COVID lockdown in my 50s after having been self employed for many years. The first job I got was awful… the company no longer exists after losing a ton of money. The second job I found is my current place of employment. I will go into my fifth year there in January. Management has changed and it is not really that great to work there any longer but it’s a job and I have learned so many new skills to add to my CV. I hadn’t worked in this particular industry before but I have developed a very branded marketing approach to my work so my presentation had to be very polished. I spent a great deal of time researching companies that I applied to so I would be knowledgeable during interviews about their operations.

    It’s only after a lot of trial and error with my CV and approach to the job search. I did get asked why I wanted to go work for others after working independently. As you well know, there are advantages and disadvantages to both. It’s nice to be your own boss but you’re never really worry free, even on holidays. Now that I am a salaried employee, I have paid leave, benefits, steady cash flow and no bookkeeping or invoicing. That’s probably not going to impress an interviewer so I told them I was eager to work for them and learn something a little different for me.

  11. Practice. Keep practicing.

    I think it was Carol Dweck who said people like the idea of learning but they hate the process of learning because it feels like failing.

  15. I mean, if you haven’t even tried at this point – the answer is clearly to start applying to positions that interest you and see how it goes. And to brush up on your skills where you reasonably can and figure out how to sell yourself for the things the positions you are interested in are asking for.

    ———–

    If you’re getting desperate for a position and are actually unable to find one:

    > And I haven’t done whiteboard interviews or LeetCode stuff in ages.

    You’ll find a lot less of this style of interviewing if you interview for tech roles at places not really considered to be “tech companies”.

    I’ll also add that the talent pool in secondary markets is a *lot* thinner and if you’re willing to live in them there’s (in-person/hybrid 3+ days in office) roles with a lot less competition and that are a lot more willing to gamble on someone with an atypical background.

    ——–

    It may not be very sexy to be doing this stuff for an insurance company or whatever that’s on the cutting edge of nothing technically. But reality is they still do write some code and they still do have projects and systems and maintenance and all that.

    And it may not be your dream to move to Omaha NE or Fort Wayne IN or Rochester NY.

    But if you reach a point where you can’t be out of work longer and you’re unable to get what you want, if you’re willing to move for the job – start considering those kinds of markets + positions if you weren’t before. It may not make you rich, but it’ll probably at least pay you a middle-class salary for the area and it beats an ever-growing <nothing> on your resume.

    Again, doesn’t sound like you’re at that position now – I’m just saying there’s a whole world of positions that many of the people I see complaining about the job market refuse to consider at all.

  16. For starters, be proud of your accomplishments brother. I’m proud of you. You’ve come along way. It takes a lot of courage, intelligence and conviction to do what you’ve done.

  17. I feel like I just wrote half of this shit in my journal. You’re not alone. A lot of us millennial tech people are at a similar inflection point.

    The only aphorism I have to offer is that “action is the antidote to anxiety.” The only way to handle the fear is to confront the fear.

    Good luck friend.

  18. You are luckier than 99% of people in the world, and just need to find a highly salaried job in technical sales, which you are already qualified for.

  19. My business failed at 37. It took me 2 years of failed attempts and 1 year of making it to the final two candidate innumerable times before something just landed in my lap, and now im onto the second thing that landed in my lap. It’s a tough spot , i wont lie, but it won’t last forever brother. You’re a smart resourceful person, you’ll land on your feet. Best to you!

Leave a Reply