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by janetacarr 1249 days ago
Personally, as a freelancer/consultant, I never think there is a right time for anything in my life. Of course, you might feel differently (and it probably is different). I'm offering advice from my perspective only, and I don't have a home to make, or children to worry about. I've been freelance/consulting/whatever for about 2 years, so make of this what you will, but I'm still early stages having just been where you're at.

First I want to say, the risk might not be as big as you might think it is. You've a pretty in-demand skill set right now, more so than most SWEs. If things don't pan out as you expect, you can always get another full-time position despite the 'looming recession'.

That said, here is some unsolicited advice. Rebuttal as necessary :)

Regarding leads/prospects, if you do decide to make the jump, chances are you'll be tapping your professional network for leads, or pitching strangers if you happen to get on a call with them via cold email. This can work for a while, maybe get your first recurring clients, but I don't recommend working with a matchmaker like Toptal, Fiverr, Upwork, or an agency.

The platforms tend to have poor pay and bad clients. Agencies will limit your ability to build a direct relationship with the clients. I know people have built successful businesses using both of them, but for me having a direct relationship with high-value clients seems to have paid off doubly as I can set my own terms (fixed rate / value based) rather than the typical hourly model. If you can/want to build such a relationship, you should *get on the phone with a decision maker* (a huge unlock for closing work). Regular dev/engineer interview channels will yield regular dev work, pay, and circumstances (maybe that's a feature for you).

After a few sales calls for clients, You may realize getting leads to come to you is best, or at minimum people should have a reason to answer your emails like having some kind of branding or marketing, so start writing, coding, tweeting, or whatever regularly to get attention. Keep at it. It's hard work.

On top of everything, you will fuck up, and that's okay, so give yourself some breathing room financially and mentally.

1 comments

FWIW, I futzed with Upwork years ago. It became super clear that it wasn't where I could sell my skills (deep backend, sre) effectively and come out with outcomes good for me and the client.

I do FTE work but occasionally dream of the side income (less so these days ha). :)

I think we all dream of side-income, but honestly freelancing on the side would be too exhausting for me (and employers don't typically like it).

I see the control over my time freelancing affords as my ticket to eventually make living off my own products (some day ;)