Anonymous
Post 06/10/2025 15:22     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:I became self-employed at 37 and had about a million saved. Now I am 42 and bill 20-25 hours per week. Last year I earned about $175K, which is enough for my needs.

I’m on my spouse’s health insurance and we have 1 young child. If it doesn’t work out, I’ll have to go back to the office one day … but I’d rather not!


What do you do for 20 hrs a week and bring in $175k?!?
Anonymous
Post 06/10/2025 15:19     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:OP here: I already have a side business that brings in 55k a year. If I were to partially retire what I mean is that I would try to scale up that business. I think I can get to over 100k in 6 months.

I have 850k in retirement. I have 375k liquid. I don’t have property (I just sold) and feel priced out of the area. I can’t move now. I also have kids. I feel like I have enough cushion to take the risk of working for myself but was wondering what others would think. I am late 40s. I have also considered switching careers but the ROI on retraining does not seem worth it.

The biggest issue is healthcare. ACA insurance is very pricey. You'll also want to coverage for your kids, I assume. Wherever you think of moving to, check the ACA marketplace first.

We were self employed for many years and had ACA insurance. While ACA has enabled many, including us, to become self employed, it is very expensive.

At 40something, you have like 15 to 20 years of needing private insurance.


My kids don't need insurance--they have it. Most people I know who do this pay $400 to $500 a month. That is not that much.


Exactly. DCUM has this absurd fear of healthcare costs because they’re all W-2 employees who only have to interact with the private insurance marketplace when they retire early at age 61, at which point health insurance *is* fairly expensive.

The thing is that insurance does become significantly more expensive as you age. For example, you should probably plan to pay over $1,000/month from age 60 to 64, so you cannot plan your future healthcare budget in the same way that you plan your future food budget, i.e., by considering what you pay today and adjusting for inflation.

But it’s really only a five-year period when insurance really is expensive. Notwithstanding that fact, you have a bunch of people on DCUM with $300K HHIs and $3M in the bank who think they cannot retire because of healthcare. It’s totally absurd; it’s like they don’t even realize that there are self-employed landscapers earning $75,000 a year who purchase their own health insurance their whole lives.

I’m 43 and pay $240/month for my ACA plan. Such a ridiculous blind spot that DCUM has.
Anonymous
Post 06/10/2025 14:27     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:That's not retiring. It's just getting paid less with the side business. Makes no sense.


My job is actually disappearing. One employer is very risky. I don't think it is going to last until retirement. I can work for my own clients and I can ramp up to make more. I would love to change careers and retrain but at my age, the ROI is really not there.
Anonymous
Post 06/10/2025 14:25     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:
Anonymous wrote:OP here: I already have a side business that brings in 55k a year. If I were to partially retire what I mean is that I would try to scale up that business. I think I can get to over 100k in 6 months.

I have 850k in retirement. I have 375k liquid. I don’t have property (I just sold) and feel priced out of the area. I can’t move now. I also have kids. I feel like I have enough cushion to take the risk of working for myself but was wondering what others would think. I am late 40s. I have also considered switching careers but the ROI on retraining does not seem worth it.

The biggest issue is healthcare. ACA insurance is very pricey. You'll also want to coverage for your kids, I assume. Wherever you think of moving to, check the ACA marketplace first.

We were self employed for many years and had ACA insurance. While ACA has enabled many, including us, to become self employed, it is very expensive.

At 40something, you have like 15 to 20 years of needing private insurance.


My kids don't need insurance--they have it. Most people I know who do this pay $400 to $500 a month. That is not that much.
Anonymous
Post 06/10/2025 14:02     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:OP here: I already have a side business that brings in 55k a year. If I were to partially retire what I mean is that I would try to scale up that business. I think I can get to over 100k in 6 months.

I have 850k in retirement. I have 375k liquid. I don’t have property (I just sold) and feel priced out of the area. I can’t move now. I also have kids. I feel like I have enough cushion to take the risk of working for myself but was wondering what others would think. I am late 40s. I have also considered switching careers but the ROI on retraining does not seem worth it.

The biggest issue is healthcare. ACA insurance is very pricey. You'll also want to coverage for your kids, I assume. Wherever you think of moving to, check the ACA marketplace first.

We were self employed for many years and had ACA insurance. While ACA has enabled many, including us, to become self employed, it is very expensive.

At 40something, you have like 15 to 20 years of needing private insurance.
Anonymous
Post 06/10/2025 13:50     Subject: I want to be self-employed/be partially retired.

OP, you say you’re in your late 40s. Have you factored in Health insurance? That can be big monthly expense.
Anonymous
Post 06/10/2025 13:27     Subject: I want to be self-employed/be partially retired.

That's not retiring. It's just getting paid less with the side business. Makes no sense.
Anonymous
Post 06/10/2025 08:52     Subject: I want to be self-employed/be partially retired.

OP here: I already have a side business that brings in 55k a year. If I were to partially retire what I mean is that I would try to scale up that business. I think I can get to over 100k in 6 months.

I have 850k in retirement. I have 375k liquid. I don’t have property (I just sold) and feel priced out of the area. I can’t move now. I also have kids. I feel like I have enough cushion to take the risk of working for myself but was wondering what others would think. I am late 40s. I have also considered switching careers but the ROI on retraining does not seem worth it.
Anonymous
Post 06/10/2025 08:47     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:I became self-employed at 37 and had about a million saved. Now I am 42 and bill 20-25 hours per week. Last year I earned about $175K, which is enough for my needs.

I’m on my spouse’s health insurance and we have 1 young child. If it doesn’t work out, I’ll have to go back to the office one day … but I’d rather not!


This is different: you are married and have back up. I don’t.
Anonymous
Post 06/09/2025 22:09     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:
Anonymous wrote:I became self-employed at 37 and had about a million saved. Now I am 42 and bill 20-25 hours per week. Last year I earned about $175K, which is enough for my needs.

I’m on my spouse’s health insurance and we have 1 young child. If it doesn’t work out, I’ll have to go back to the office one day … but I’d rather not!


Oh be quiet. You became a stay at home mom and your husband supports you.


There was no gender specified and they earn 175k. Learn to read.
Anonymous
Post 06/09/2025 21:54     Subject: I want to be self-employed/be partially retired.

Anonymous wrote:I became self-employed at 37 and had about a million saved. Now I am 42 and bill 20-25 hours per week. Last year I earned about $175K, which is enough for my needs.

I’m on my spouse’s health insurance and we have 1 young child. If it doesn’t work out, I’ll have to go back to the office one day … but I’d rather not!


Oh be quiet. You became a stay at home mom and your husband supports you.
Anonymous
Post 06/09/2025 21:48     Subject: I want to be self-employed/be partially retired.

I became self-employed at 37 and had about a million saved. Now I am 42 and bill 20-25 hours per week. Last year I earned about $175K, which is enough for my needs.

I’m on my spouse’s health insurance and we have 1 young child. If it doesn’t work out, I’ll have to go back to the office one day … but I’d rather not!
Anonymous
Post 06/09/2025 21:22     Subject: I want to be self-employed/be partially retired.

I’m planning on doing something similar, except I am already self-employed. The good thing about being self-employed (at least in my case) is that you can scale the business up or down to work the number of hours you want.

I’m 43 and plan on semi-retiring at 45 with a paid-off $500,000 condo and $1 million in investments. However, I plan on keeping my business but just working 1-2 hours per day and earning about $50,000 per year.

I estimate I’ll pay around $10,000 in taxes and be left with $40,000. I further estimate I will end up spending about $50,000 per year, so I’ll just have a gap of $10,000 to fill. That would amount to a 1% withdrawal rate from my portfolio.

I consider that pretty risk-free and expect that my portfolio will continue to grow. If you do have an entrepreneurial/self-employment bent, it’s much less risky to semi-retire because you can always ramp up your income in the future if needed. In contrast, if an employee decides to semi-retire at 45, there’s no way they’re getting their job back at 55 if they need it.
Anonymous
Post 06/09/2025 21:09     Subject: I want to be self-employed/be partially retired.

That's me. I need $4k to live. $2k for housing and $2k for spending. Easy.
There's plenty of money in investment accounts in case I go over budget.
Anonymous
Post 06/09/2025 20:22     Subject: I want to be self-employed/be partially retired.

I don't want to work for employers anymore. I just want to have my own clients or change careers.
I am late 40s. College is funded for kids.
I am not a fancy person.
I may even move to a LOC area when my kids go to college in 8 years.

What would your number be (retirement savings, cash on hand or home equity) if you wanted to just take a risk and work for yourself and not be a member of the full-time rat race. I have a decent amount in retirement and cash. I sold my house. Divorced (not married).

Anyone want to share their number if they were me in this scenario?