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I've been my own boss for ~ 7 years. 2 of those as a contractor, the other 5 as a SAAS founder.

I've been able to take any day off I want, but I have NEVER been able to switch off. It took me about 4-5 years to finally be relatively OK with it. Annual leave is far better.

I've taken a bit of a "holiday" this year by taking a full time role for ~8 months and it's been a great opportunity to recharge and work with amazing people that are much smarter than me, but I'm already feeling the pinch to go back and do my own thing.

Having said all of the above, I'm very lucky that I'm 10+ years in the software industry and I've always got the option of a great full time role to fall back on.

All in all, so far I'm not sure it was worth it. I wouldn't have been as successful and fulfilled if I kept my full time role, but I'd be a hell of a lot happier.




I know what you mean. My support demands are quite low and just 9 to 5 and Monday to Friday but I can never completely switch off. I'd like to go on holiday without a phone and laptop.

Having said that I've never had the same level of autonomy in previous jobs. This has outweighed all the downsides.


Did I read this right? You took a full-time job as a "holiday" from the stresses of being your own boss? I guess the grass truly is always greener.


Yep, and it's been great!




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