In June 2022 I quit my last full-time salaried position at Loom and since then I haven’t looked back. The timing was right: things were more or less back to “normal” after peak Covid, I had a pent-up desire to get out and travel, and I had just about reached the limit of my ability to tolerate corporate culture. I spent the summer traveling in Europe and Mexico before ramping up a new career as a freelance analytics consultant.

On top of Brač island in Croatia - no KPIs here

In Sarajevo, eating ice cream where they shot Franz Ferdinand. We'll never know his opinions on the Modern Data Stack.

I must stress that I have been gainfully employed this entire time; “I’m freelance consulting” is not a euphemism for “I’m unemployed.” I’ve been fortunate enough to be able to work with a diverse set of paying clients and make a living this way, and eventually I was able to take the opportunity to help build a product of my own, Zetta. At the same time, working freelance isn’t quite “living the dream” and it came with its own surprises and downsides that I’m still wrapping my head around.

Working a salaried job is a simple proposition: you punch in for your nine-to-five and in exchange you get the same paycheck twice a month. Of course it’s not quite that simple, especially in the tech industry. How hard do you actually work on any given day? Is nine-to-five more like eight-to-six plus answering emails at night? Can I get away with skipping company all-hands? These are all choices that you have to make, but individually they don't feel particularly consequential.

By contrast, when you’re working contract gigs you become all too aware of the value of each hour. When I was juggling multiple contracts, I found myself scheduling out each of my days to bill the precise number of hours I needed to. Sure, you have the freedom to work whenever you want and to take time off in whatever big or small increments that you want, but if you’re like me it’s easy to get distracted trying to figure out the optimal arrangement in any given day, week, or month.

I see three key advantages working contract vs. working salaried:

1. You can get paid more: when you swap your stagnant corporate salary for an hourly rate the pay increase can be substantial
2. You can work a more modest number of hours per week: you’re not tied to the standard 40+ hour work week; you have the flexibility to scale down to something a bit more sustainable
3. You can go on vacation whenever you want: we all know the tech industry practice of “unlimited vacation” is a scam. As a contractor, you can actually go on vacation as much as you please without having to get approval from anyone or feeling guilty

Starting out, I definitely pursued the high-earnings, high-vacation strategy. It felt nice to indulge in my desire to travel frequently while also sticking it to the man by making more money than I ever did full-time. But, the longer hours at home became stressful. It’s also difficult to have to rationalize your free time when you know that you could be working instead, which adds to the stress. It can even bleed into those vacations when you start wondering if the opportunity cost of taking 1-2 weeks away from work is really worth it.

Eventually, I transitioned to more of a lower-earnings, high-vacation, low-workload lifestyle which feels more sustainable (however, that was undermined a bit by founding Zetta). My original goal for shifting to freelance work was to work less, so it felt counterproductive to be putting in so many hours. I also didn’t feel like I had anything to prove by earning more money - If I can work enough to stay afloat while having more freedom and leisure time, that’s worth a pay cut to me.

As the above section illustrates, the new stressors that come with contract work make it all too easy to start looking back on full-time salaried work with rose-colored glasses.

The most salient aspect of contract work is just how hard you end up having to work. If you’re being honest with yourself, how many hours a week do you actually spend working at a salaried position? It can be hard to tell, but if you actually tracked it I bet it wouldn’t be more than 25. Yet, when I started working freelance I had the 40-hour workweek as my anchor. So, imagine my surprise when I realized that working anything over 30 hours in a given week is actually a lot of work!

Granted, I did have the tendency to work quite hard when I was a salaried employee. But, working freelance has made me realize how little incentive I actually had to put in that effort. After working contract for a while, I imagined that if I did ever go back to full-time I would make a concerted effort to slack off way more than I did before. What are they going to do, fire me? Not to mention the additional stability that comes with full-time employment. Sure, they can lay you off whenever they want, but at least there’s not a defined contract end date from the start and you’d probably get some severance.

So, my time spent as a freelancer has given me a different appreciation for the things I took for granted as a full-timer. But, that’s ignoring all of the things I take for granted about freelancing. I would honestly rather put a bullet in my head than attend another company all-hands meeting. Setting BOUNDARIES is much, much easier as a contractor and it feels so, so satisfying to ignore my inboxes when I’m off the clock. Yes, working contract can be more difficult on a per-hour basis, but its also more tangible and satisfying. On paper getting paid a salary to browse Reddit all day sounds like a good deal, but I know from experience that zoning out in your home office eight hours a day day after day just doesn’t feel good. I’m happy to be able to work for myself, strip out a lot of the bullshit, and feel like there’s a bit more cause-and-effect with my time spent working.

That lack of cause-and-effect is one of the things that really makes salaried work frustrating. You can work hard, distinguish yourself, take on extra work, but none of it is really correlated with compensation in a meaningful way. The oligarchs would like to convince us that the tech industry is some kind of meritocracy, but that’s an obvious load of crap. Most promotions are just based on tenure, not performance, and they’ll always come up with a new excuse to keep the annual raise pool as small as possible.

Working for yourself offers an opportunity to escape all of this, but it comes with its own traps:

• You can negotiate your own rates for projects, which will generally be a lot higher than the equivalent salary, but you have a lot less data to rely on when setting those rates. When I was first starting out, I tried to be aggressive with my rates but I still wonder if I left money on the table by not pushing the envelope a bit more
• Getting paid by the hour, if you choose to go that way, can turn into a slog because you’re committing yourself to a certain number of hours regardless of how much work you get done. There’s still an incentive to work efficiently because you want to demonstrate value to the client and earn or maintain their trust, but you lose the significance of actual project milestones.
• A lot of people will encourage charging on a per-project basis to avoid the issues with hourly billing. While it makes sense, I’ve had a hard time applying this to analytics specifically just given the amount of scope creep on the average project and the nebulous nature of any analytical projects. I’ve found an okay balance by negotiating flat monthly retainers of hours, but this still leaves me with a decoupling of progress vs. compensation

Building Zetta has given me a third perspective - I’ve sunk a lot of hours into building a product, and my own compensation is directly tied to the success of the company (especially because we have not and will not be taking outside investment). But, the optimization here is even murkier: with a product like Zetta, there’s always something new I could be working on that could pay dividends, but it’s not clear what will have the best returns. In the meantime, most of my marginal effort goes uncompensated. If the product proves successful I’ll reap the benefits of my hard work, but there’s also a lot of luck involved and the market does not necessarily reward the best product (that’s not sour grapes, it’s just reality - something that we knew when we started).

I like to think that building a product from scratch has given me a better perspective on my experience working freelance. When I committed to Zetta, I knew that I would be putting in a lot of unpaid work over the first couple of years, and this has helped me realize how wonderful it has been to be able to earn any amount of money for part-time work in tech. I've also learned to relax a bit and stop optimizing my time so aggressively.

Going forward I hope that I can continue to sustain my freelance business even if (or perhaps especially if) that means working fewer hours. It’s possible that circumstances will compel me to seek full-time employment again. In fact, I'd be curious to jump back into a salaried role in the future just to see how my perspective may have changed. Who knows: maybe I'd actually enjoy it! Until then, I'm happy to just keep my options open.