I have a opportunity to make a pretty decent living at this safe job. I would much rather chase my dream job, but ive been failing at succeeding for 2 yrs now. Im 29y/o and at square one due to unfair life circumstances. So i feel im behind and need to start my career now. What is the best choice to make? Keep trying to be successful with what im doing or get the safe job until i retire?

28 comments
  1. If you’re able to support yourself, you don’t live with mom and dad, your dream job is attainable and will afford you a better quality of life, and you have no dependents, fuck it. Life’s about risk.

  2. Is your dream job something you could do as a side hobby and have more fun at with the freedom of not having to make money with it?

  3. Can your dream job be a hobby? If so, take the safe job until you master the dream job. Then make the switch when it starts becoming sustainable.

  4. there isn’t really a safe job imo. anything can change in this world over the course of a few years. so i would go with the dream job. “behind” is not really a thing in terms of someone’s work life. i’m sure you’ve seen the memes about such and such person only got started doing [thing they are respected for] at an older age. it’s true.

  5. If you wanna chase your dreams, you had better have a pretty solid safety net. I wouldn’t personally do it unless I had enough money in the account to cover all of my living expenses for at least a year ( including fuel at $5 a gallon, mortgage/rent, food at Double its current price, electricity at Double its current price, and about 10 grand in savings just in case something happens)

  6. Hard to make a balanced suggestion with the limited information given.

    It’s always ok to chase your dream job… as long as you accept the consequences, if, for whatever reason, you are unable to reach/fulfil it.

  7. Life is short dude. Life is really really short. Do you want a safe comfortable life, or do you want a fulfilling life? The choice is yours. It’s your life and you actually can do whatever you want with it. It’s your choice

  8. Too little info……. If your dream job is to be a rock star and you are 29; take the job. If your dream is to manage a coffee shop; follow the dream!! The real basic question is realistically, how likely is the dream to come true at your current age and progress………….

  9. When you make big bets, try to capture as much upside as you can while making sure your downside risk is hedged.

    Like, if you dream of being a rockstar, you need to make sure you’re positioning yourself such that there’s somewhere to land on if that falls through. If you’re a truly fantastic guitarist, then maybe you can make networking for your band also be building the network to position you as a viable session musician. Or if you are really good at mastering your own tracks, maybe you can position yourself to be able to fall into audio engineering.

    I built startups when I was younger because I dreamed of running a high end tech company, but I also knew that experience would position me far better to create a lot of value at other people’s tech startups and earn a better income than I could have otherwise, so there was actually no real risk.

    I explained this to people at the time who thought I was taking some unhinged risk. Then when my startup died I did just that and it worked well, I immediately made a lot more than I would have with a job under my major.

    Idk what other people call this, but I call it taking advantage of asymmetric risk.

  10. If you want to ponder “what if” when you’re in a wheelchair many years from now then keep the safe job.

  11. When your career sucks, my 12 year career sucks, its reliable and will always be there for me but fuck it, might as well try for what you want, but always have the “just in case” option. That maybe the most important thing you can do for yourself besides taking care of your health.

  12. Keep your job but see what you can do on the side, talk to your manager or boss or whatever and try to chase your dreams All my luck goes to you

  13. When you’re young and have time to course correct if the dream job doesn’t pay off

    As you age, you run out of bullets in the gun, and you need to make them count.

    At 29, you can attempt a dream job, but you absolutely need to hedge your bet and have a Plan B. You also need to be methodical and disciplined about your pursuit of the dream job.

    This usually involves working harder than you want to work or making sacrifices you don’t want to make.

    It’s worth noting that it’s quite likely that you have no idea what your dream job would be. I’m 44 and have my dream job, but I couldn’t tell someone how to get this job, and I couldn’t have predicted my job would even exist.

    While you pursue your dream job, your Plan B should involve gaining some kind of mastery in a profession that people predictably pay for.

    Mastery yields the dream job, not the other way around, as people commonly conceive of it.

    Once you have mastery, you will encounter people who “need someone who knows how to do X” and you can, to some degree, dictate your terms and be picky with your employer.

  14. Can you support yourself financially? Do you have any dependents? If you answered no to the first question and/or yes to the second stick with the safe job.

  15. You’re not behind. It’s not a race. Do what you feel you would regret less in the future. Money comes and goes, as does time, and goals. Determine what you really feel is important to you and pursue that.

  16. Always. You only live once. I’ve been chasing different dream jobs all my life and every 6 years I’m back at square one. I’ll never be rich, but who gives a fuck? It’s a hell of a ride.

  17. I guess sooner is the better, because you can always bounce back on other career’s opportunities

  18. You answered your own question. When it’s your dream job.

    When wifey and I got out of the Marine Corps, we went back to school on the GI Bill. I majored in Business, she majored in Accounting. Our family tradition has been the fire service since the the ’60s. Wifey and I had talked about it and she was ok with it. She was always proud of me and would even rub it in her co-workers faces! I was the only firefighter spouse in the whole firm. Our kids were the reality check, to them I was just dad.

  19. NONONONONONONONONOOOO!!! Chase the dream job. Chase it now. At 29 you’re not going to be the best at it, but find people who are, and learn their ways. Employers want specific experience, and if you take some other job, you will *never* get in.

  20. I did exactly that at your age. I had no kids when I went for it and still none now, so no huge risks. It has gone pretty well so far, so I’d say go for it.

  21. I can empathize with this. 26 now and wondering if I should go to school to get a degree in computer programming and possibly have my degree by the time I am 30 or just stick with a job a friend of mine is offering me. Only issue is that this job is very labor intensive and I am trying to avoid that. Jobs like that just aren’t for me anymore. If I go with his job, I can have a long career, but I will be more likely to be doing that labor intensive stuff for the rest of my work life. From my limited experience in life, life is short but it is also long, go for your dream. If you were to actually “fail” then at least you would never have to deal with the pain of regret and you can always find a safe job through the connections you make or have made.

  22. Dude, you’re 29. If you don’t have kids and other stuff, GO FOR IT!! You will never be as young as you are now. If you have those responsibilities, then talk with your partner. At the end of the day, working toward something with your whole heart and failing is infinitely better than never trying, you’ll always be left wondering “What If?” so avoid that regret. I’ve done my best to follow that sort of stuff, and though I’ve failed more often than I’ve won, the wins were sweeter and more valued for the struggle. Life won’t had you things, you gotta work for it.

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