What to do next, when you “made it”?

I am a guy in late 20’s, last few years I was freelancing with on/off success, always stressed about getting the next client to pay my bills. Recently I started a long-term remote work relationship with an amazing startup and suddenly all my financial worries are gone. I make multiple times more than the national average and make more than 10x more than some of my friends.

But here’s the thing, I lost my motivation and feel empty, I jumped ahead too fast. I don’t know what to do. And I can’t talk about this with anyone, people would think I am a jerk to complain about making so much money while still having so much free time left. I now feel like even a bigger outsider to people around me, than I already was as a freelancer working from home. Then I watch some youtube videos about chinese mothers getting paid peanuts to sustain their families and feel even more alien. I was always super passionate about learning and evolving, but now that I reached the financial stability, I don’t feel the same way anymore.

I am wondering if learning the skills I was chasing was just conditional on trying to achieve some financial success. This is not how I imagined finally not struggling financially would be. I really don’t like to hide things, but I can’t talk about this without alienating people around me either. I am lost. What do I do?


  • Looks like you got yourself a nice pair of golden handcuffs πŸ™‚ But in your post you mentioned something important: “free time”. If you have some free time available, simply find another area of your life were you can feel passionate and evolve too. It could be another aspect of your professional life such as starting up your own company slowly when you have time. Could be learning new programming languages, learning more about software architecture, product or project management and the list goes on.

    You could also find another aspect of you life that is not related to your work: traveling, new spoken language, volunteering, music instrument, etc.

    Finally, if you feel bad about making that much money, simple spread the wealth around on you family and closest friend. Invite them for lunch or the theater, etc. Or simply donate to some important causes.

    Passion and interests may shift over time, you simply need to find new ones.

    Good luck!

    • Look at it this way, if the startup went bust, where would you be? If it is not in a good place financially, use that extra time and money, to pay off house, invest well, set up side gigs,pay for courses to learn about things that are interesting/useful to you(money and time well spent) If you still have too much lots of charitable causes.

  • Build something great.

    Im raising a $3MM round to build a Clean-tech plant if your looking for something of substance. The Im going to build this energy device that will change the future of humanity – if i dont die from trying to escape the hollowness through substances. id like to share my email, but this is supposed to be an anonymous place.

  • Sounds to me like with financial pressure removed you are left with a pretty existential question of “What’s worth doing?” or perhaps, more pointedly, “What can I be committed to in my life that’s worth being committed to?” Or even pointed, “What do I want to stand for in my life?”

    Importantly, this is less about what to “do” and more about the kind of human being you want to be in the world – About meaning vs. activity. This can happen when we find ourselves somehow not caught in the drift of the familiar in our life (as in familiar everyday pressures or constraints, or habits we’ve fallen into for one reason or another.)

    It’s awesome that you have come to this place in your late 20s – Rather than having this show up, as it does for many people, in their 40s as a “mid-life crisis.’

    My suggestion: While you are clearly in an uncomfortable space, rather than relating to your situation as a problem, what if you related to it as a big opening for possibility in the direction of authenticity vs. necessity. What’s worth doing because it’s worth doing (in terms of contribution) vs. doing something because you need to. This is a chance to discover what it means to be truly generative in an authentic way vs. simply reacting or responding to your circumstances.

    Rather than hurrying yourself out of an uncomfortable place, the most powerful way to deal with this kind of transition is to let yourself actually experience the discomfort (the actual physical sensations and feelings of it!), knowing that as you do that, you are making way for something new to emerge. Sounds to me like you are in a transition that is developmental and related to maturity.

    It sometimes sucks to feel the discomfort, but it’s this kind of approach that supports real development.

    As you hang out in this space, something you can pay attention to is: What do you find yourself drawn to? What brings you joy? What seems to evoke curiosity in you? What seems to allow you to feel both excited and relaxed at the same time. While journaling isn’t for everyone, when in this kind of process, it can be really helpful!

  • {"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}

    You may also like

    >