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Comment by sheepdog | Hacker News Reader

I'm 40-ish and have been self-employed for about 5 years now. I have no plans to go back to full-time employment. You should consider that route.

There are very few benefits to being a full-time employee that you can't obtain yourself. Plus, having a wide portfolio of freelance clients helps insulate you against business downturns and future age discrimination.

Granted, it's a lot of work to curate a good client list and network yourself. But it's actually the same amount of work as jockeying for promotions and good projects at a corporate job.

And there is some risk involved in working for yourself. But at a corporate job there is similar risk; you are always one bad quarter away from being laid off.

Working for yourself IS a career. Consider fortifying your position and staying the course.

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I find freelancing to be a lonely experience. I don't get to talk shop with co-workers as well.

>I have no plans to go back to full-time employment. You should consider that route.

Just because that is your preferred experience, you want me to follow it? Okay but my personal goal is to be employed full-time and you seem more interested in making me more like you, and not like who I want to be.

If you want to help me on my goal to get employed full-time, I'm all ears. But I am not looking to be convinced to stay freelance.

My apologies. You have to be yourself, and there are some social benefits to going to the office. Assuming your freelance work counts as past experience, and that you are trying to stay in the same space, I'd offer these tips:

1. Tell prospective employers that you were very successfully self-employed, not unemployed. No one want to hire someone who is perceived as inexperienced, so you've got to make it clear that your freelance work was every bit as much "real work" as corporate projects.

2. Build a portfolio of freelance projects that are impressive. When talking about them, mention how you had to do "full stack" or "end to end" work. Make it clear that you deliver awesome stuff and work independently.

3. Sometimes getting a job is a "who you know" situation. Gently ask your freelance clients if they are hiring, even if it's temp to perm.

4. If you lack experience, try to get a "foot in the door" by taking a lower position. For example, if you can't get on the dev team, can you get hired as tier 2 support? It's not ideal, but you might be able to move to the dev team in 6-12 months if you are a good worker. Or you can use that as a stepladder to pivot to a competitor.

I hope this helps. Good luck!

Do you have any advice for making that transition? I'm a SWE with about 3 years experience. I'm hoping to make this type of transition in a few more years. Also, are you in the US? Does paying for your own insurance significantly erode your earnings?

I'd recommend moonlighting to get a feel for it. It's a good way to test drive without the "sink or swim" pressure. You can get gigs from your network, partner agencies, or Upwork.com. (The pay sucks on Upwork, but it's good experience and you'll build your confidence.)

Another (more risky) approach would be to deliberately work at a 5 or 10 person company. This will give you a feel for how to "hunt for your own food" but still have a team backing you up. (I subcontracted at a few small agencies during year one, just to keep some cash flow going.)

I'm in the US, so healthcare insurance is a big concern. But corporations aren't the only ones who can buy health insurance. Depending on a lot of factors, it costs roughly $500-$1000 a month to ensure a family. Some chambers of commerce have a group plan that you can buy into.

On the surface, that sounds like a lot of money. But in reality, it's only $12k a year. If you are a primo engineer making $100k+ per year, save up over several years and you have 2-3 years of runway to pay for your insurance. The moonlighting will help with this as well.

Good luck!

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