The Startup Junkie #3: Solo Flight

In the first two Startup Junkie posts, we discussed some reasons to work for a small company instead of a larger, established one. In this third edition, the Junkie poses the question: if you’re going to take the plunge, should you work directly for a startup — as a full-time employee — or might it be better to sign on as an independent contractor?

I should note first of all that 1) I’m talking independent contracting here, not working for a recruiting agency; and 2) this option is not for the newbie. Don’t even think about freelancing if you don’t have at least one solid full-time stint under your belt. Few people will be crazy enough to hire a freelancer without a resume. Right out of college, you have no contacts anyway. Who are you going to ask for a job?

Let’s assume you meet the criteria. Going solo might not have crossed your mind. You can probably rattle off plenty of good reasons to stick with full-time employment, but let’s list some here, just for the sake of argument.

  • Benefits. If you work directly for a startup, chances are good you’ll get benefits. Not guaranteed, but good. However, you can ask a higher hourly rate if you’re on your own. If you have any experience, you ought to be able to ask enough to cover the cost of your health insurance. You’re young and healthy; you might be carrying too much health insurance anyway.

  • Work environment. It’s nice not to have to run down to Staples every time you run out of Post-Its or printer paper. Your coffee will probably be free. Your soda may even be free, and I bet you don’t have a snack machine installed in your living room. Balancing your checkbook is bad enough; the idea of setting up a corporation and bank accounts for your own business is probably making your ears bleed. Did I mention taxes?

  • Security. If you’re a full-time employee, you are guaranteed a paycheck every couple of weeks, and maybe even a yearly raise. As a contractor, you’ll be sending invoices monthly or biweekly. Startups are notoriously finicky about when they pay their bills, and their schedule might not match up with your wallet’s. You’ll spend a good chunk of time pinging your clients and bugging them to pay you.

If you’re like me, though, you’ve had one or more paychecks show up late — or not at all. Contractors may get cut first when downsizing time comes — but when things go south, you have fewer ties to the company. The relationship is B2B, not personal. Not getting paid on time? Go look for business elsewhere. One good thing about being on your own is detachment.

Closely related to detachment is freedom. As a full-time employee, you’re committed to spending all day — every day — working for someone else. If you work for them on a contract basis, at least you can take the time to go out and look for more secure work should the need arise.

Which leads us to work environment. If you work for yourself, you own your schedule and your workplace. Usually you can work from home where interruptions are fewer, and your boss’s boss isn’t treading the halls to see if you’re actually working. There’s no conflict of interest in taking a personal call or a few minutes of time to pay your bills online. Working from home can be dangerous if your time-management skills aren’t sharp, or if you have little ones at home.

Which path you choose depends a great deal on your judgement and the specifics of the situation. How well do you know and trust the ones in charge of that small company? Are they going to look after you and your career, or are you just going to be a resource to them? As a contractor, you represent less overhead than a full-time employee. You don’t take up office space, they didn’t buy you a computer, and the tax situation is better. That’s a good position to be in if the money dries up. Regardless, you’re perfectly justified in shopping around when that happens. Your time is spent making you — not your client — money.

So what do you really gain by signing your life away? Is that full-time position at a startup that much more secure?

You’ve worked a job or two, right? Count the people you know in your field. If you’ve been working five years or so, you have some contacts you can hit up for work. Every company I’ve ever worked for hired me, not because I made a cold call or resume submission, but because someone I knew got me in the door. Flying solo is not for the faint of heart, but it’s a big step towards owning your own career.


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