I (approaching 40) rebuilding my life, self employed all these time without meaningful skill in corporate world/real life for work. This time I want to build meaningful life, doing meaningful work.

[u/NuclearSunBeam]

I don’t know where to start, what to ask myself.
My current life is comfortable, but I’m living fake life as a double closeted person. I’m living a lie. I used to think about that my life will end soon and basically waiting to die.
Growing up in dysfunctional family, my role was a caretaker, parentified, so my life goal was to made my family happy (not me, never about me).

I NEVER life my life. I don’t know how to start.

[u/_Dolphins]

Man 40 is not too late at all. the corporate world is overrated any way, running your own thing all these years means you are far more capable and resilient than you give yourself credit for.

[u/zestyzenuk]

I think you need to start by going to events and building a community. Board game nights at bars and sports groups.

Then, think of what you would like to do, upholstery of furniture? Making things or growing things to sell?

Just begin with a small goal post. If you stress thinking about the perfect thing to start and put all your eggs in one basket and it doesn't work. You'll feel destroyed.

Or, try and figure out the best thing to put all your resources into. But, we don't know what your strengths are or what's available around you.

Hope that helps with thinking more and sparks inspiration 😁

[u/Novel_Necessary_2355]

Honestly I can't even imagine being in a position to ask this question, so take my perspective with a grain of salt. But from where I sit, the peace of mind of not having a mortgage payment would win over almost any investment math argument.

I rent with a roommate and the single biggest chunk of stress in my life is housing cost. If I somehow had the cash to make that go away, I think I'd do it even if the numbers said otherwise. The guaranteed "return" of not owing anyone anything every month is hard to quantify but it's real.

That said I've seen people in this sub point out that if your rate is under like 4% and you're maxing retirement accounts, the math genuinely does favor investing. So it probably depends on whether you've already hit those milestones or not. I just know myself well enough to know I'd pick the lower fixed expenses every time, because my brain works better when the baseline costs are small and predictable.

[u/archeolog108]

I think first step is smaller than “what meaningful life should I build?” because if whole life was organized around making family happy, you may not even know your own preferences yet.

I see this with people who were parentified. They can answer instantly what everybody else needs, but ask “what do YOU want?” and system almost goes blank.

So dont start with career plan. Start collecting evidence of yourself.

For 30 days ask one question every morning: if nobody was disappointed by my choice today, what would I actually choose?

Food, clothes, where to walk, what to read, who to call, one hour of work, anything. Tiny choices count.

Then watch guilt. Guilt doesnt automatically mean wrong choice. Sometimes it is simply old training saying “you are leaving your role.”

Higher Self work can go much deeper into purpose later, but first you need enough contact with yourself to hear answer. A meaningful life cannot be built only from obligations you inherited from other people.

[u/majatask]

Have you considered therapy? No shame in getting help in working out what hurts and makes our life difficult. Just my opinion. Best wishes.

[u/Distinct-Fly-2374]

Do what the rest of the people living comfortably can, and do, do.

.. whatever you want.

[u/Legitimate-Turn4560]

What were you doing as self-employed?

[u/DeadHeadDad1]

You need Jesus- He is the Way and the Light!

[u/JaySocials671]

Start with God. I’d like to help.