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Ask HN: I love freelancing. Then why do I hate it?

2 points by overthinkerJS ↗ HN
I've been freelancing all of my working life and thus have (luckily) built a solid reputation & network that allows me to ask for generous sums of money for project without me working long days. So I am earning a nice living that I'm very very thankful for.

However... why for the last 5 years have I tried launching a gazillion projects with the hope of leaving my clients behind and create a more 'passive' and more scalable source of income?

Why do I on one hand, love working with people. But at the same time don't want to abide by their rules anymore and do my own thing.

Is there anyone around here that managed to successfully transition from that level of freelancing to being a business owner of some sorts that is earning them more from freelancing AND is actually more enjoyable?

I'm torn by the daily switch of love/hate of my day to day work.

4 comments

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verdverm
I hear you, trying to do the same thing. I have my own company I work on, on the side. One thing I do is take some time off of the freelance, like only work 20 hours for a week, or take two whole weeks off.

To move off of the freelancing, there needs to be other income, which I also expect to be less. So revenues or investment will become the milestone.

overthinkerJS
How do you currently go about investing? (If any)
verdverm
You mean seeking investment and how I go about finding investors? I'm currently gearing up to seek a seed round this fall.
bytemode
Loving it because you're making money and working at your own convenience.

Hate it because your clients or mostly shitbags and you sometimes end up working on projects you don't like.