Breaking up with your startup: Why I chose contracting

Before I start, a quick disclaimer; I have been contracting for all of one month! I’m about to tell you why I made the switch and some first impressions, but to be honest I have no idea how long I plan to do it, or if it’s a good idea for you. Hell, I barely even know you.

I’m going to dispel with any boring backstory about myself; suffice it to say that I’ve worked at a few startups of varying sizes over the last 5 years, and I’ve learned a few things. I worked with some great people, I had some great times, I made some money, and then I left. Why?


Working on a product you believe in is great, really it’s the best. But once in a while you also have to ask yourself, am I still learning, am I still growing? Here’s something you already know — the pace of change in the tech industry is mind-boggling, particularly in web development. It seems like every few months a tech giant releases “the new hotness”™, some library or framework that we all have to learn or be left in the dust. I’m being glib but in all seriousness, usually these are worth learning because they are meant to make your life as a developer easier and introduce new possibilities. The flip side of the coin, unfortunately, is if you aren’t learning then you’re not really staying level as a developer, you’re getting worse. As a full-time employee at a company, especially a large compartmentalized one, you run the risk of becoming siloed and acquiring a great depth of knowledge in one aspect of development, say database optimization, while your other skills go unpracticed and slowly fade. But what happens when you decide to leave, only to learn that a tech giant has just released the “new hotness database” which is self-optimizing? That would be putting your eggs in one basket, which is not a great idea, regardless of the basket’s quality.

Contracting allows you, with some persistence, to find projects where you can use the tools you want to learn. If you’re great at backend development but middling at front-end, you can take concurrent contracts for fewer hours at different rates and bring your front-end skills up to speed.

Of course sometimes you also get to choose to work on products you love, but as a contractor that should be secondary to making sure you’re learning, which in itself is secondary to getting a good rate. Being a contractor is not about falling in love, unless it’s true love. More on that later.

Work / Life Balance

Here’s another poorly kept secret — the tech industry has a culture of masochism. This is especially prevalent in startups, where 60 hour work weeks “aren’t really that bad” and red-bull (or adderall, let’s be real) fueled all-nighters are glorified, as long as the bug got fixed, or the demo worked, or whatever. Don’t get me wrong, sometimes that kind of behavior is necessary, fun, and rewarding, especially when there’s a lot at stake. But when you get funny looks for leaving the office at 5 on a Friday, it’s gone too far. And peer pressure is not even the most insidious problem—that would be caring too much. There is always a feature you can improve, a bug to fix, and more test coverage to catch up on. As a salaried employee in the age of instant access and remote working, you will find yourself working at all hours out of the best of intentions — a sense of responsibility to your customers. It’s not sustainable! Some of the most dedicated people I’ve worked with were also the most likely to burn out, and when that happens the costs outweigh whatever benefits were gained every time.

As a contractor, I commit to as many or as few hours as I want. I can work one big project or several small projects. I can take no time between contracts or a month off. I’ve also found that my at work time is more focused — I almost never browse the web or check my personal e-mail while I’m on the clock, since my efficiency is more closely tied to my earnings than as a salaried employee.


Lets talk dolla dolla bills y’all. Suppose you work a full year contracting at $50/hr. Assuming you work 40hrs/week and take 2 weeks off, what is your equivalent yearly salary? If you said $100k, you’re right. If you thought “whoa that’s more than I thought”, then that’s what I thought too. Now lets take a few other factors into effect.

As a salaried employee, how often can you expect a raise in compensation? I would guess about every two years on average. But what if the market for your skills is adjusting at a much faster rate? As a contractor, you can work a 3 month contract at $50/hr, then try to increase the next one to $60. Now that is a pretty palatable sounding increase to an employer, its only $10, but its a 20% raise in compensation, so your equivalent salary is now $120k. Next time maybe you can go up to 70, or you have to go back down to 50, but you have the option of adjusting your rate at the speed of the market, rather than the speed of your employer’s choosing.

Then we can come back to the point of flexibility and work / life balance. Lets say you’re an experienced developer making $100/hr, or $200k/yr. That means you could work 20 hours a week and still make $100k. What salaried job in tech that pays $100k can you take where you won’t feel guilty working 20 hours a week?!

Finally there are the tax benefits. These are tedious, but basically you get to write off a whole bunch of stuff and potentially slide down a tax bracket by setting up an LLC or Corp.

So with all that, would I go back to being a salaried employee at a startup or tech giant? Of course! As long as it’s…

True Love

Being a contractor is like being single. You meet new people, you learn interesting things, you do some good work together, and then you say goodbye. Being a salaried employee is like being in a relationship. At its worst a bad work environment can have the qualities of a bad relationship — abusive behavior, crazy expectations, and the like. Then there’s the in-between job, something that you’re comfortable with… but every day is the same and after a while the job hasn’t changed, but the passion is gone. And then there’s true, burning love, where every day is an adventure. That will mean different things to different people — maybe its an opportunity to work on a product that you believe will help a lot of people, or work at the largest data center in the world, or build a team for a young company, or pursue your own startup idea. Sometimes you‘re not expecting love to comes along, but you have to be open to it when it does. The point is you should fall in love at least once. And when you’re single, you never know if the next person you meet is the One.