How I built a six figure side income

In two years, I tripled my income.

Let’s set the clock back 3+ years to April 2020, when I was let go from my day job leading content for a startup. I was making an upper five figures salary, but working 80+ hours a week and completely burnt out. When I was let go – in the midst of a pandemic – it shook me to my core. Who was I outside of my day job? I didn’t have a clear answer.

I started to reach out to friends and pick up some fractional work while I searched for a full-time replacement, and I was able to land a few steady clients. That process opened up my world to steady fractional work, and a career made of many parts rather than just one linear trajectory. And it’s only continued to grow since those early pandemic days.

Tips for starting to build your side income

My experience is my own, but I often have friends who tap me for advice as they are looking to build out a freelancing business. I don’t have all the answers, but I wanted to outline seven important things to consider as you get started.

1. Find a specialization and go wide, not deep

My expertise is in brand and content, but it’s multifaceted. I’ve written press releases and I’ve written campaign copy. I’ve ghostwritten white papers and I’ve drafted scripts. I’ve done everything from UX copy through to penning my former CEO’s speeches.

And I’ve done this across industries, in everything from advertising to hospitality to fintech, entertainment, and beyond. I’ve found that honing in on an expertise is more valuable than an industry, but dialing that expertise up or down is so important. I don’t expect every client to need a script, a go-to-market strategy, UX copy, email campaigns, SEO audits, and more, so I first try to understand their goals, then make strategic recommendations based on where I can be helpful, and lastly take their queue on where the most acute needs are.

I’ve found that I’ve had more success with this approach than friends who specialize more deeply in copywriting. Because I have a wider breadth of content offerings, I can be more flexible with freelance programs for a client, and it makes it that much easier for my clients who don’t have to find a separate person to conceptualize their website versus write their pitch deck copy. As a result of saving them that added legwork, I can charge a higher rate than I would if I was just offering content writing, for example.

2. Consider the right day job for yourself

As I mentioned earlier, before I started freelancing, I worked a job which often started at 5:30 a.m. and didn’t end until 10 p.m. There’s no way to freelance in that environment, no matter how much I loved it at the time. If fractional work is part of your personal goals, you’ll want to find a job that gives you space for that. Saving freelance for the weekends will make for a pretty brutal existence where you are working seven days a week.

If fractional work is part of your personal goals, you’ll want to find a job that gives you space for that. Saving freelance for the weekends will make for a pretty brutal existence where you are working seven days a week.

There is obviously a certain amount of privilege that comes with this statement (and this article as a whole), but to the best of your ability, you’ll want to select a job where you can work 40 hours or less, and so you have a couple of hours in the mornings or evenings to take on freelance. Part of my initial financial success was because I was weaning off of my 80 hour work weeks, so I didn’t mind working 60-65 hours a week. Now I never work more than 40, but that’s due to a blend of (1) seniority in my role and efficiencies I’ve developed because of it, (2) finding a flexible day job, and (3) purposefully containing the time in which I work.

3. Be great to work with

There’s not much to say on this point, but just be really, really great to work with. Be the kind of freelancer that everyone wants to recommend to their friends. Be exceptionally attentive to your client’s needs, responsive over email, and kind in meetings and communication. State your deadlines and stick to them or beat them.

I don’t agree with “underpromise and over deliver”. Rather, just promise you’re going to do best-in-class work and deliver best-in-class work. Don’t ever let your personal frustrations with a project affect how you communicate with the folks on the other side, even when they are difficult (that’s the kind of stuff you vent to friends or family for!).

4. Ask your friends for help

For help and for help with your rate! When I first started freelancing, I felt so embarrassed about asking anyone for assistance; it felt desperate to me. The thing that I forgot, and I find that many others do too, is that people want to help you. Your friends love being of assistance. When I landed my first two retainer contracts (10 hours/week at $150/hour, which is my standard rate), it was because:

I asked my former Founder of the company that let me go if he had any friends he could introduce me to. He did, and I worked with that client for over a year.
My next boss (and now friend) saw my work and asked if I could take on freelance assignments. I said yes, and that contract lasted for about a year as well.

Asking friends about your rate is important, too. I believe in rate and salary transparency and I’ve had at least a few jobs where I’ve undervalued my rate because I didn’t know who or how to ask. Now I talk openly about what mine is in the hopes that it might help my friends or former colleagues know how to set their rates or be more open about their operations to others.

5. Mostly say yes, but know when to say no

Most of my success is because I say "yes" to a lot of the offers that come my way. I’m also lucky here; most of my work has come in from friends or friends-of-friends, former collaborators, or even current colleagues, so I know it’s generally good people to work with.

In the very few times where I’ve been a little uncertain about whether or not I will jive with the client, I either state my concerns out the gate and set up some exit strategies for us both (“let’s try a trial project and see how we like working together”) is a great one and it’s not disingenuous at all.

It should be a mutual fit (not just about my own sense of fulfillment) or I simply don’t take the work. I also have a few principles under which I absolutely would not take on freelance work (i.e., something doesn’t align with my ethics), which has only once been an issue with incoming work.

I would recommend writing down those principles somewhere and returning to them every so often. It can help in those moments of scarcity when we feel like we might want to take on work because the money is there, but in your heart-of-hearts you know that the output will suffer from your distaste for the company. Don’t set yourself up for that! Know your no’s, but aim for more yes’s.

6. Don’t be sketchy

This might seem like an obvious one, but it’s so important to me. I have always been up front with my employers that I freelance on the side, and I’ve always told my freelance clients that I have full-time work. I don’t book over work or meetings time with freelance work. I never work with a freelance client that is competitive with my day job (and I never work with a freelance client that is competitive with current freelance clients as well).

This might come from my own high propensity for feeling guilty 24/7, but I also know that it’s valued by my employers and my clients. It also helps solve for the earlier note of finding a day job that works. If I tell an employer that I freelance on the side and they have an issue with that, I know it’s not the right place for me to work.

7. Talk to an accountant early

Know your options when it comes to building out your freelance business. You may want to file as a sole proprietor or set up an S-Corp or LLC. Far be it from me to explain any of the nuances there, but talking to an accountant early on can help you prepare for financial planning and taxes. When you’re a freelancer, you shift from paying taxes annually to paying them quarterly, so there’s quite a bit more to plan for. As the old NBC public service announcement goes, “the more you know.”

While these seven tips are helpful to keep in mind, I also recognize that they don’t pave a pathway towards immediate side income success. Unfortunately, I can’t do that for you because so much of that relies on your unique talents! I can tell you a few of the key actions I took in the wake of being let go that helped me build a thriving freelance business:

I got my materials together, including a personal website and portfolio
I reached out to former colleagues with wide networks and I asked them if they knew of anyone who needed help
I offered some of my services pro bono to support local businesses that I loved (for my own personal gratification, because I had the time, and for the network effect)
I prepared for each intro from those friends and proactively drafted some suggestions for how I could improve their brand presences. In short: be prepared!

The other caveat I’d like to add is that when I started building my side income, it was April 2020. I had a lot more time indoors and, as mentioned above, I was starting to wind down my expectations of working 80+ hours every week. That is to say, I had ample time indoors to work and an outsized expectation of how often I should be on the clock. In the ensuing years, I’ve slowed my freelance business some and will likely take in mid-five figures this year. The tips above helped me get started and I believe will help me if/when I choose to ramp my business back up. I hope they help you, too.

The very first place to start was with a personal website. If only Polywork had existed in 2020 when I was building mine! You can also get your personal profile and portfolio started in minutes on Polywork.

Disclaimer: This is based on my own personal experience. I’m not an accountant or a lawyer, and if you’re thinking about starting a business on the side, you may want to consider consulting those professionals.

I built a six figure side income in 2 years: Here’s how I did it