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Started By
Message
Working for yourself
Posted on 12/31/25 at 6:30 am
Posted on 12/31/25 at 6:30 am
Dear tOT,
As I've gotten older, it has become increasingly more difficult to hold a job for more than 2 years. I get fed up easily. Even when I do a good job, there's a sense of meaningless that creeps in. This wasn't the way it used to be in my teens and throughout my 20s. Even working shite jobs like unloading trucks, when I did a good job I felt good about it. As if I was doing my duty. Lately when I do a good job, my stomach drops and I feel like I'd be better suited doing the same good job for myself.
It seems I can't manage to work for others. I want autonomy to set up my own systems and do things my way. I'd like the ability to choose what work is worth my time. I think that's the most pressing matter. I feel like I'm wasting my own time as the years tick by.
I don't like this sensation. I'd like nothing more than to work a normal job and be happy. But I can't. And not in the "work sucks" way. It's more of "My body is rejecting this and I need to change my situation."
I've started small businesses in my 20s and made a couple bucks here and there, but never really followed through because I was always happy with my main source of income. That's not the case anymore, and I feel like I am going to be forced into sink or swim entrepreneurship sooner than later.
Thank you for reading. Please discuss.
As I've gotten older, it has become increasingly more difficult to hold a job for more than 2 years. I get fed up easily. Even when I do a good job, there's a sense of meaningless that creeps in. This wasn't the way it used to be in my teens and throughout my 20s. Even working shite jobs like unloading trucks, when I did a good job I felt good about it. As if I was doing my duty. Lately when I do a good job, my stomach drops and I feel like I'd be better suited doing the same good job for myself.
It seems I can't manage to work for others. I want autonomy to set up my own systems and do things my way. I'd like the ability to choose what work is worth my time. I think that's the most pressing matter. I feel like I'm wasting my own time as the years tick by.
I don't like this sensation. I'd like nothing more than to work a normal job and be happy. But I can't. And not in the "work sucks" way. It's more of "My body is rejecting this and I need to change my situation."
I've started small businesses in my 20s and made a couple bucks here and there, but never really followed through because I was always happy with my main source of income. That's not the case anymore, and I feel like I am going to be forced into sink or swim entrepreneurship sooner than later.
Thank you for reading. Please discuss.
Posted on 12/31/25 at 6:32 am to Odysseus32
After reading this, if you do strike out on your own, how are you going to keep from becoming "fed up" with your clients?
This post was edited on 12/31/25 at 6:33 am
Posted on 12/31/25 at 6:33 am to Odysseus32
Pretty common feeling. But working for yourself is also a skill, and a lot of people do not have it.
The same way some people can’t work from home effectively, but on steroids.
The same way some people can’t work from home effectively, but on steroids.
Posted on 12/31/25 at 6:33 am to Lonnie Utah
quote:
After reading this, how are you going to keep from becoming "fed up" with your clients?
This is a fantastic question, and one that I've had to ask myself and part of the reason I am not jumping.
Posted on 12/31/25 at 6:34 am to Odysseus32
How old is older just retire baw
Posted on 12/31/25 at 6:34 am to Odysseus32
Realize that there is a lot of value in knowing you will get paid every two weeks (or regularly). Working for yourself means you may not get paid, or worse yet, just see your money disappear into the void. Big question - are any other people dependent on your income?
Posted on 12/31/25 at 6:35 am to Odysseus32
Go start that business. With you leaving every 2 years you’re not exactly the picture of stability. Dealing with clients might give you perspective. You’ll either enjoy it or possibly develop peace with just doing a job and going home.
This post was edited on 12/31/25 at 6:36 am
Posted on 12/31/25 at 6:35 am to Odysseus32
quote:
This is a fantastic question, and one that I've had to ask myself
It seems like to me what you need is emotional intelligence and discipline. In your case, that is what's going to help you thrive in a business environment (either working for someone or working on your own).
This post was edited on 12/31/25 at 8:20 am
Posted on 12/31/25 at 6:37 am to Odysseus32
Having worked for myself, as well as for others- all i can say is that everything in life is a trade-off…. For me, ill take the trade-off of dealing with clients and having a lot on my shoulders, in order to ‘be my own boss’… for other people they might be willing to put up with some micro-manager or having to punch a clock, in order to feel like they have more “security”.. i think job security is usually a myth though .. We are all wired differently, sounds like you’re the type of person who would value autonomy and independence, and think it’s worth the risk.. i am the same way .
Posted on 12/31/25 at 6:40 am to Odysseus32
It's rough.
I'll take the regular hours and paycheck even with the aggravation.
I'll take the regular hours and paycheck even with the aggravation.
Posted on 12/31/25 at 6:43 am to BK Lounge
quote:
for other people they might be willing to put up with some micro-manager or having to punch a clock, in order to feel like they have more “security”
I think this is where I literally will not function. If I'm being micro-managed at a job, I make plans to leave. I haven't come across it in accounting so much, but when I was younger if I started a warehouse job and there was a micro manager, I would leave sometimes immediately. I can't deal with it. Not "I don't want to put up with this". I will literally just leave the situation. I have faith I can find something else, and at the end of the day I always feel like I'll be fine.
Even when we lived 2000 miles away my mindset has always been to evaluate the situation, if the reward is not there for what you're dealing with, you can find something else. You'll be okay.
This is where I have to be careful. Clients are your boss when you're self-employed. You have a lot more, and you have some flexibility to choose some of them, but if you're starving you might have to eat some shite. Can I deal with that?
Posted on 12/31/25 at 6:46 am to Odysseus32
Age? Current income? Number of dependents?
These 3 things help people who’ve done it before advise.
These 3 things help people who’ve done it before advise.
Posted on 12/31/25 at 6:47 am to BeerMoney
33
90k
Me and my wife.
Edit - I’m 33 not 32. Forgot.
90k
Me and my wife.
Edit - I’m 33 not 32. Forgot.
This post was edited on 12/31/25 at 6:48 am
Posted on 12/31/25 at 7:05 am to Odysseus32
Is wife supportive of your ambition? Does she have income and willingness to keep things afloat while you struggle to start up? Or is a divorce incoming in 3, 2...
Posted on 12/31/25 at 7:11 am to LA Lightning
The most supportive person in my life. Divorce isn’t coming. We’ve been through a ton together, it would have happened by now.
Posted on 12/31/25 at 7:11 am to Odysseus32
Dropped my engineering job in 1996 and started working for myself. Like anything, its great and not great. It takes a lot more time, effort but has rewards. Ive been doing it now for 30 years. Two different ventures for me and I would say both have been rewarding and successful.
I think the biggest issue is preparing for retirement. Its harder. No paid holidays, you control the raises and work.
If I could roll back 30 years, I would prep for retirement more than I did. Though I doubt I am going to retire anytime soon, baring a health issue, I still would have done more. I am not the kind of guy to just sit around but having that option would be nice. I got lucky and some other good things happened for me that took care of my retirement but it is still something I would have done a better job at
If you have the right mentality, it can work. As for your wife, she must be supportive 100%. I was lucky with that one but not every woman is going to be on board and its understandable. My wife trusted me and it paid off
I think the biggest issue is preparing for retirement. Its harder. No paid holidays, you control the raises and work.
If I could roll back 30 years, I would prep for retirement more than I did. Though I doubt I am going to retire anytime soon, baring a health issue, I still would have done more. I am not the kind of guy to just sit around but having that option would be nice. I got lucky and some other good things happened for me that took care of my retirement but it is still something I would have done a better job at
If you have the right mentality, it can work. As for your wife, she must be supportive 100%. I was lucky with that one but not every woman is going to be on board and its understandable. My wife trusted me and it paid off
Posted on 12/31/25 at 7:14 am to Odysseus32
What kindof business do you want to start?
Posted on 12/31/25 at 7:28 am to Odysseus32
quote:What is your skill set & initial plan? To start a business from scratch & need 90k as a base is a tall order for most.
33
90k
Me and my wife.
Posted on 12/31/25 at 7:43 am to Odysseus32
Certainly not impossible but certainly not easy. I decided to do this in my late 30s about 5 months before Covid hit. For 4 years I fought like hell to keep my people with families employed, all bills paid on time to any vendor and hustled my arse off to get us certain projects.
This shite is not for the meek. It helps that you have some Capital going into something like this but a lot can go wrong if you’re not thorough. Other than a strong work ethic, I sincerely believe you need to be a person with integrity. Sure, we all know some of these sleeze balls that have none and it seems they’re are getting by without repercussions but it will ALWAYS come back to bite them.
We’ve been incredibly blessed after struggling close to 4 years but we have been rolling the last 17 months. Have been blessed more than I could’ve hoped for (knock on wood).
There’s a lot of liability and responsibility you’re accountable for. That weight can feel pretty heavy sometimes. I’m not trying to scare you but there are a shite load of things you need review and pray about before just jumping in. I’m not saying don’t not do it because of fear of failure. If you’re scared of the horses arse you’ll never see his face. Just make sure you’ve done your due diligence.
ETA: And sometimes I do want to go back to consulting for big firms like I did in the past. When you own your own though, my downtime/ off time has been almost zero the past nearly 6 years. Some of that has to do with me though.
This shite is not for the meek. It helps that you have some Capital going into something like this but a lot can go wrong if you’re not thorough. Other than a strong work ethic, I sincerely believe you need to be a person with integrity. Sure, we all know some of these sleeze balls that have none and it seems they’re are getting by without repercussions but it will ALWAYS come back to bite them.
We’ve been incredibly blessed after struggling close to 4 years but we have been rolling the last 17 months. Have been blessed more than I could’ve hoped for (knock on wood).
There’s a lot of liability and responsibility you’re accountable for. That weight can feel pretty heavy sometimes. I’m not trying to scare you but there are a shite load of things you need review and pray about before just jumping in. I’m not saying don’t not do it because of fear of failure. If you’re scared of the horses arse you’ll never see his face. Just make sure you’ve done your due diligence.
ETA: And sometimes I do want to go back to consulting for big firms like I did in the past. When you own your own though, my downtime/ off time has been almost zero the past nearly 6 years. Some of that has to do with me though.
This post was edited on 12/31/25 at 7:48 am
Posted on 12/31/25 at 7:53 am to Odysseus32
Employing people is somewhat a giant baby sitting service. Personalities, conflicts and trying to create a good company culture is challenging….
If you’re going to employ people, go in eyes wide open…..
If you’re going to employ people, go in eyes wide open…..
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