Diving Into Freelancing vs. Starting On The Side

Title Photo by Greg Rosenke on Unsplash

Getting into freelancing as a Product Manager usually doesn’t just happen ‘en passant’ — in our space, it usually follows some elaborate evaluation of your professional (and/or personal) life’s priorities and at least some upfront groundwork. 

Accordingly, there’s a spectrum of options to realize this foray, with the extremes being playing it safe with a side hustle and taking the plunge going all-in, as well as some middle ground in there.

So, what are my choices?

a. Going all-in

Quitting your employed job and going full-throttle into freelancing is obviously the most direct road to success — given that 

1. you actually use all the time you just freed up, 
2. you didn’t completely miscalculate your chances and 
3. you’ve got a financial buffer to last you at least 3 (rather 6 months) while you figure things out.

b. Side hustlin’

If you pick up freelancing as a side hustle next to your full time job, you really minimize the risk while building up; however, most contracts for PM freelancers will exceed your remnant capacities, so you’ll need to make a more substantial choice eventually. Also, working a second job next to a 40 hour work week (and more importantly, actually being any good at it) will take a toll quickly.

I’ve taken that all-in route, and I don’t regret it one bit. A few comments on this, though:

• I was privileged enough to be able to build up a couple of month’s worth of buffer to carry me through the initial drought, plus living in Germany, I had the option of claiming unemployment benefits, which would’ve given me over a year of runway. This will make a temporary dent in your lifestyle, but the last thing you’ll want is to try something new, and before you know it, you’re broke and homeless — and it’s not even the actual chance of that happening, but also the anxiety that the prospect of that induces.
• I already had so many things going on outside of my regular job that I had to come to terms with the fact that a day can’t have more than 24 hours and thus, I’ll need to make an all-in decision. I would’ve loved to go in & come out of this as the guy who managed to build this new career while he was still going at the current one, and was able to do it all at once, but I had to accept that it wouldn’t work. So, ask yourself what the compromise between how you want to and how you can do it is.
• As a product manager, picking up freelance gigs will quickly produce a conflict with your employed job. There just aren’t a lot of freelance PM gigs out there that require less than 10 hours per week. If you’re looking to freelance e.g. as a designer, the demand landscape makes a gradual segue much more feasible.

So, what other options do I have?

c. The Segue

As a middle ground, you can reduce your full time job’s hours to part time, investing the other half of your time into building your freelance career; this is definitely the most weighted middle ground between risk and opportunity.

Depending on your domestic labor legislation, you might be entitled to reducing your hours, so definitely go and check that. Beware though that aside from the fact that most employers will only begrudgingly tend to this request, they’ll consider you on the long way out if you do that, so if you do this, consider it a point of no return.

While I mentioned that freelance Product Management contracts with less than 10 hours volume per week are hard to come by, contracts with 20–30 hours weekly volume are fairly common; with smaller projects, a client won’t require someone full-time, and/or might not have the budget for it. At the same time, it’s pretty hard to find on-staff Product Managers that are interested in working part-time (and harder to find for fixed-term projects). 

So if you’re lucky and you can coordinate the whole “dancing on two weddings”, you can run on two tracks for a while and basically A/B-test both experiences. Bear in mind though that:

1. Eventually, you’ll need to make a choice — as in personal relationships, double-tracking it is not a sustainable option. Make sure to use your time to evaluate and to help make up your mind.
2. If you end up opting to remain in the employed world, you might need to look for a different employer — if you’re lucky, your existing employer will “take you back in” and scale you back up to full-time, but (also depending on labor legislation) they might not be obligated to do so, and decide to not do it based on how they feel about you after everything.
3. If you’d intend to tap into unemployment benefits after parting ways with your employer, your benefits might also be reduced by half — e.g. in Germany, part-time employment only entitles you to part-time benefits.

Cool — what else do I need to consider?

Here are some Key Takeaways:

1. If you want to start, start early: even if you’re going down the side hustle road, you can get a head start on getting a tax ID/business license, building a website, starting client acquisition and other necessary activities. You don’t only want to be dealing with those when someone’s actually interested in your services!
2. Really think about what option works best for you: risk-averse, but have a lot of grit? Build it as a side hustle. More of an all-or-nothing-person? Just quit your job & go all-in — even if it doesn’t work out, you’ll easily find another employed job. Just make sure you’ve got a couple of months’ rent & basic living expenses set aside!
3. As for getting started, it’s all about that first client — but that’s another post for another time.

So, how about it?

Are you considering going freelance, and weren’t sure how? Has this piece brought you a bit of clarity? Do you have any more open questions? 

Or if you’ve already gone freelance — how did you start out? We’d be super interested in learning about others’ stories! Please leave us a comment below!👇

And as always,

Thanks so much for reading!

We acknowledge that with the 5 minutes, you could’ve literally done anything else, and we’re very honored that you decided to dedicate them to our piece! ❤️