I never thought I'd be an entrepreneur

Honestly, I intended to actively avoid entrepreneurship. I’m an introvert, I like structure, and I don’t like asking people for things; running a business requires you to power through all three. Among the many reasons I picked a career path in computer science was that it was pretty straightforward what you did with a Comp Sci degree; you got a job as a programmer and people gave you money for it.

Then I unexpectedly lost my job and had to figure out something to do until I found a new one. I remembered that someone had asked me not too long ago about whether I knew anyone who’d be a good hire for a webmaster position, and got in touch to ask if it was still open, and that’s how I got my first regular freelance client.

This makes it sound easy, honestly. The problem is that freelance isn’t consistent; people you’re working for may need a lot of help one month and may have things running really smoothly the next. Ideally, you’ve got a handful of regular clients, but you need to wear several hats as a solo business, which means that you are suddenly also marketing, sales, human resources, and business development. I really like the freedom time-wise I get while working freelance, but it’s also time I spend worrying about the fact that I’m not making money for those hours.

It’s been a bumpy road, but I feel like I’ve learned a lot at minimum about how to make it smoother. Here’s some of my takes.

1. Your best clients are people you know

There’s a lot of people who list part-time contract gigs on places like LinkedIn; I can’t say that I’ve ever heard back from any of those. The fact of the matter is that as a solo freelancer, you don’t have the manpower of an agency with an entire department to work on RFPs, and if you’re a solo freelancer who’s good at your job and having to pay for your own health insurance, you’re probably expensive to hire.

In general, like with most work stuff, a lot of it is about networking. It’s a fine line to balance between making people feel like you’re only in their spaces to shill and not getting any leverage at all, but it’s good to keep an ear out for what people mention around you. If someone mentions that they need help with something in your field, mention that if they can’t get it figured out, you do that kind of thing for freelance and can figure out how to work with their budget.

2. Speaking of which: don’t adjust your rates, adjust your approach

Being able to figure out how to work with people’s budgets is key—small business isn’t always going to have a lot of money, but they might come back to you a lot over time if they’re comfortable with you. Maybe they don’t need the most cutting-edge solution, or the cleanest code; they just need something you can put together that’ll hold up for a long time, and that isn’t hard to explain to new hires.

Okay, yeah, maybe they don’t have the budget for a full $3000 overhaul, but what can you do for them in the time $300 will get them that’ll make things easier?

3. Start keeping an eye on taxes immediately

At least if you’re in the US, you will have to pay estimated taxes, and the best time to do that is to start with the current quarter so that you don’t have to pay back taxes when April rolls around. Estimated taxes are based on a guess of what you’ll earn each quarter in income without withholding, and they can be pretty steep. Make sure to build in space to be able to pay them. (State and Federal also have separate estimated taxes, so that’s fun.)

At the same time, also keep track of your business expenses. You can claim deductions for them, up to a point, and it can make the difference between paying hundreds or thousands and getting a refund. You can do this with office equipment, educational expenses, sometimes utilities if you use a certain percentage of your home as an office.

4. You will also probably have to register as a business

I discovered this because my payment processor stopped processing my payments until I could verify I wasn’t doing some kind of shady thing, which meant I had to register an LLC in my state, take a selfie, take a picture of my ID, etc. for them to approve within a couple-week turnaround or they’d shut down my account. If you’re only doing a little business, it might be fine, but “a little” stops somewhere around $10k.

5. Don’t invest a huge amount of money right away

You don’t know what the future holds, but you should know that you can always scale up if you need to, so start with free or cheap. Maybe you won’t actually do that much freelancing; maybe you won’t turn out to like a particular product as much as you thought. Also, if you’re a solo operation, most of the time you don’t need a paid package, and the free tier on something will work just fine.

So like, yeah, I know I just said to keep track of your expenses so you can deduct them from your taxes, but also don’t spend just for the sake of it; see if you can get by with something inexpensive or free first.

6. Start it up while you’re employed

Do it in your off-hours while you still have a salaried income. Then go full-time once you have a decent client base; you’d have to be pretty lucky or pretty well-connected to go right from layoff to being full time self-sustaining freelance. Keep in mind that most businesses that hit it big have a lot of investment of venture capital, and it’s incredibly hard to pitch if you don’t have a new or trendy idea.

Is it worth it? I think the answer will be different for everyone. I’d love to not freelance—for one thing, I like having a solid separation of work and rest hours because I’m not good at enforcing the division myself. I’m also not great at business networking, so it’s hard for me to close on potential leads. But there’s also a lot of upsides to the contractor life—a lot fewer meetings and a lot more latitude with organizing your life. You just have to be ready to either slow-roll it, or to really hit the ground running.