Lessons from a Year of Freelancing

Today, I celebrate my Freelanciversary: it’s been one year since I quit my day job to make my living as a freelancer — and all the thrills, chills, and Ramen that entails.

I’ve learned a lot over my past 12 months of ups and downs, so I thought I’d share what worked well for me, what didn’t, and what I plan to do next.

But first, a clarification.

This isn’t my first go-round as a freelancer. Back in 2005 I quit my day job to freelance for a living, and that lasted for almost 7 years until I took a day job in 2012. So no, this wasn’t a year of trial by fire and me figuring out how the freelance world works. Instead, it was more like, “did I learn my lesson the first time around, and am I any better at freelancing now than I was then?”

The answer is yes… and no. But I’m learning, and that’s what counts.

See, having done this before, I knew the challenges. I knew what mistakes I had made last time. And I knew myself a little better — or at least I thought I did.

But, as always, life always has a few curveballs to throw.

So here’s what really happened.

Freelancing Lessons: What Worked?

Through a mix of talent, experience, and the help of my network, some things went very well for me this year, and I managed to keep myself (mostly) afloat in the feast-or-famine freelance world. Here’s what worked, and why.

Stability Is Key

You can’t work if you can’t eat. And for freelancers, eating isn’t always a guarantee.

The most important part of adulthood is ensuring that you have enough money coming in to cover all your necessities on a monthly basis. When you have a day job, that paycheck is automatic and guaranteed. But when you freelance, those paychecks are intermittent and arbitrary — you literally never know when you’re going to get paid, or where your next job is coming from.

How do you solve that?

Get retainer contracts.

When I left my day job, my former boss retained me on a contract through the end of the fiscal year. The hours weren’t guaranteed, but the rate was. And because they hadn’t replaced my position, I inevitably got a little work from them each month, which they paid reliably and quickly.

I also had one freelance client I’d worked with before, who rehired me on a monthly retainer that he paid in advance. That was super helpful… although it had a catch, which I’ll explain in the next section.

Between those two clients, I wasn’t making enough to clear all my bills and save for taxes, but I was pretty close. And anything I made beyond that would balance me out, or help me get ahead.

Keep the Pipeline Moving

New work is the lifeblood of your business. It’s also your key to peace of mind.

I knew my contract with my former job had an expiration date, so I kept my eye out for a client that I could replace them with when the time came.

When that contract ended, I began working with a new client under the same arrangement — no guaranteed hours, but a standard rate and a flux of work on a monthly basis.

Granted, it’s impossible to budget against a varying workload of hours. And yes, being on a flat retainer that’s not tied to an hourly wage, or a tally of hours worked, would be ideal. (My preference for project-based pricing over hourly pricing should be its own blog post.)

But having these types of arrangements is critical for making sure there’s something coming in at all times. The real key is scaling your revenue up, so there’s always more money coming in than you need. I’m not there yet, but that’s a goal for year two.

Mining My Network

Everyone I worked with this year was either someone who hired me before, someone who knew me for awhile, or was the result of someone recommending me. I didn’t get one single job that was a complete cold contact.

I’m not complaining, either. I enjoy working with the people I know. I’m just pointing out that when you offer a service, it’s far more likely to be purchased by people who already trust you — at least at first, before you’ve built a portfolio that speaks for itself.

Your network is your most important business growth asset. Make sure your network knows what you love to do so they can refer you to their networks.

Owning My Time

One of the main reasons I returned to freelancing was because I wanted more control of my time. I felt like there were more things I could be accomplishing if I weren’t trapped in a rigid 9-to-5 structure. This turned out to be a double-edged sword, and I’ll go deeper into its downside in a moment.

But first, I must admit: controlling my time has actually been one of the biggest upsides of my past year, when I’ve been able to take advantage of it. Some of those benefits include:

• Working on what I want, when I want, and where I want
• Working from cafes, rather than being stuck at home alone
• Reading or watching movies in the middle of the day
• Waking up when I’m awake, rather than with an alarm
• Being outside a lot more often (since I walk everywhere)
• Naps (boy, do I love naps, let me tell you…)

But the most potent upside to controlling my own time has been this: I don’t need to work constantly in order to survive.

When I crunch the numbers, I need to earn X every month in order to break even.

Right now, I’m not quite making X every month… but I’m close. And I’m doing it by working fewer than 40 hours a week. And I can work those hours when I want, depending on the project — which means I can bulk them all up at the beginning of a week, if that makes sense, and then I can buy myself a few days to do other things.

This is exactly why I wanted control of my own time again: so I could make the things I was passionate about, and build a new career for myself.

Now, here’s why that hasn’t quite happened… yet.

Freelancing Lessons: What Didn’t Work?

Having years of freelance experience plus years of self-awareness doesn’t necessarily mean I’m an expert at freelance or life. Here are all the lessons I had to learn (again) the hard way.

Stability Requires a Cushion… and I Don’t Have One

You can’t work if you can’t eat, and this has definitely been a year of beans and rice.

When I left my day job, I had a small nest egg. That, plus my two initial clients, plus a third gig I picked up in my first month, all contributed to a nice early windfall.

And then that nest egg got steadily chipped away, until it was gone.

As I mentioned, one of my clients pays me a reliable retainer in advance, which is great… but it’s based on a batch of hours to be worked. Some months, there isn’t enough work in their own pipeline to require my help, so those hours spill over… and over… and over. They always get used eventually, and the retainer always gets refilled, which is good. But the frequency isn’t as frequent as it needs to be in order for me to budget for it as a reliable monthly guarantee, so I now view it as a nice bonus when it comes around. And that means I need other clients to fill in that stability gap.

I also got whacked with an old debt that I wasn’t expecting, and that ate over $3000 of my nest egg in one month.

I let my health insurance lapse because I couldn’t afford the premiums anymore.

And when my former day job contract ended, I hadn’t quite lined up its replacement — and certainly not at the frequency of hours I was losing — so I had a very thin summer.

How thin?

In July, I earned $150.

Granted, I did much better in other months. But when I look back at my ledger for the year, I see that I only reached my break-even point twice. In every other month, I came close… or less so. This explains why my nest egg is nonexistent, and why I’m spending more time hunting for new gigs than I am producing work: my pipeline is still being built.

But this instability also creates a second problem.

I Haven’t Slept This Poorly in Years

When you have steady income, you can focus on what you’d like to do with your expendable cash in your free time.

When you don’t have steady income, you spend all your time thinking about where your next check is coming from.

This means I have less time to create — or to relax, or plan my future — than I would like. Because every time I take a break from hunting down jobs, a little voice in the back of my head reminds me that I may not be able to buy groceries next week. It usually reminds me of this at 3 AM, as I lie awake and contemplate the seeming futility of my existence.

But then the sun comes up and I have a cup of coffee and anything seems possible.

So, yeah, it’s a crap shoot. What I need to do is make it a little more stable than a rigged game where the house always wins.

Part of my challenge is that I’ve realized I have no natural inclination for sales. Maybe it’s just my inherent distrust of commercialism, but I have great difficulty explaining why someone should hire me. This is why I get most of my jobs from my network — because I don’t have to cold sell them quite the same way. And that means instead of learning new sales techniques, what I really need is a portfolio that helps explain my value proposition to the people I’m already interacting with.

There’s just one problem.

My Portfolio Is Strangely Empty

One of the most surprising hurdles I’ve had to clear is that, after 12 months of freelancing… I actually have nothing to show for it.

Of all the hours I’ve logged for clients, the vast majority of them were internal or procedural or other behind-the-scenes work that doesn’t result in a finished product or a specific case study.

Even the media I did produce is absent, because the finished product is out of my hands. I wrote scripts for two multimedia projects a year ago that still haven’t been released to the public. I wrote another video script in March and I still haven’t seen the finished piece. And a project I’m working on right now is shaping up well… except it’s intended for internal distribution only, which means I doubt it’ll even be made available in excerpts for the sake of portfolio reference.

All of this makes it very difficult to get new clients, because when they ask what I’ve been working on, I literally have nothing to show them. It’s a strange paradox, and I haven’t quite found a solution yet. But when I do I’m sure it’ll make landing new clients, and more work, much easier.

If I have time for them.

But boy, do I ever.

That Nebulous Time Thing

Remember how great I said it was to have complete control of my time?

Here’s the problem with that: it means I need to have a goal, momentum, and willpower.

Without those three ingredients, my endless expanse of free time turns into a terrifying abyss of sameness, in which entire months can slide off the calendar without me even feeling like a day has passed, and suddenly it’s October and I realize I still haven’t done half the things I planned to do this year… or this lifetime.

Where does the time go?

Online. Surfing. Using Twitter and Facebook as a social outlet, because I don’t quite have the spare cash it takes to be social in person.

When most of my work is digital, it means my computer is both my office and my playground — and that means I can sit down to work at 10 AM, realize it’s now 5 PM, and discover that I’ve only done 2 hours of billable work and spent the rest of my time going down Twitter rabbit holes and reading “just one more article” on Aeon or Grantland (RIP).

So, yeah, having complete control of my own time is great… but it means I actually need to be responsible for that control, and to control myself as well.

Which leads us to…

What’s Next in Freelance: Year Two?

Well, it’s complicated.

See, I’m skeptical of establishing goals just for the sake of having goals.

My past experience has proven to me that I don’t take arbitrarily assigned goals seriously, unless they’ve been assigned to me by someone else. I have no trouble meeting deadlines, but I’m terrible at giving myself structure when the only person who suffers if I stray from it is me.

So instead of clearly-defined, data-driven goals, here are the four areas of my freelance life that I intend to improve in the next year.

More Money

Holy Jesus, yes, more money.

Where does more money come from? More work. And let me tell you something: I love to work.

I actually overlooked this at my day job, because — quite frankly — there were long stretches where I felt like I wasn’t really doing as much as I could. But when all the deadlines converged, and the pressure skyrocketed? That’s when I felt most engaged.

It’s always been that way, at every job I’ve ever had. Or the events I’ve organized in the past. Or the web series I’ve produced. Or pretty much any instance in which I’m so busy that I don’t really have much free time.

I’ve realized that as much as I enjoy having control of my time, what I enjoy even more is solving problems and being useful to others. And money is the byproduct of being useful.

So, naturally, my next area to improve is to be…

More Useful

Nothing makes me happier than making someone else’s life better.

When I’m writing video scripts, my goal is to deliver information in an entertaining way — and I like producing videos that help people learn things that make their lives better.

When I’m project managing, or brand consulting, or market researching, or product launch planning, or conducting a digital media audit, my goal is to help other people understand how they can accomplish their own goals faster and more efficiently by removing unnecessary steps and clarifying their own value proposition — and I like helping people do the jobs they love more effectively.

And when I’m blogging or speaking, I enjoy the performative aspect — but I also strive to deliver insights that help people think differently and lead them to make improvements in their own lives, so they can be more competent, more confident, and more satisfied.

So, yes, I’d like to do more of all that in year two — and for a wider variety of clients. (If you’re reading this and you haven’t hired me yet, now’s your chance. Contact me and let’s figure out what we can do together.)

More Making

Before I started writing this post, I thought about my rationale for leaving my day job. I wanted more control of my time, yes, but what did I want to do with that time?

I wanted to do less marketing and more making — specifically, of media.

In thinking about what I’d really like to be doing, it all revolves around media and entertainment. It always has. But in preparing to write this post, I accidentally honed in on what aspect of that field really interests me. Yes, it’s the storytelling. And yes, it’s the creation of media and characters and experiences that become cultural and generational touchstones.

But what I really want to be doing is helping talented people create something amazing together. And that means I want to do two things:

I want to run my own live event brand, and I want to own my own production company.

Now, no one’s going to pay me to do either of those things for them. That’s not freelancing; that’s entrepreneurship, and it’s a distantly-related subject to the topic at hand here. (It’s also not something I can do tomorrow, given that my main diet right now is essentially peanut butter and Craisins.)

But knowing that about myself helps me understand what kinds of skills I need to learn if I want to be successful in those fields, and who I need to network with, and what kind of value I need to bring to the people who would pay me to do those things — by sponsoring or investing in me.

And that means I want to do more work that results in media that the public actually engages with, so I can hone those skills and expand my network and achieve these latent career goals that have been in the back of my head for the past 20 years or so, and which I keep deferring.

If sitting in front of a computer screen for the past year and feeling like only a month has passed has taught me anything, it’s that life moves fast, and I can only keep telling myself “I still have time to do this” before I’m either lying or dead.

And that brings us to the final area of my life that I need to improve:

More Self-Control

I almost said “more willpower,” but that’s just a subset of self-control. It’s a tool that can help you stay on task and see it through, and that’s great. But honestly, the better you are at self-control, the less willpower you really need, because you won’t be straying off the path in the first place.

To me, more self-control means doing things like blocking out distractions, staying ahead on projects, pitching new clients, hunting down work, meeting new people, and maximizing all this free time that I sacrificed my stability and my revenue in order to have control over.

If all I wanted was more stability and more money, I could get another day job. And that might even be the smart choice. Believe me, I’ve spent a LOT of time thinking about where I’d be right now if I was still at my old day job — and while I’m convinced that I made the right choice, the hollow echo in my bank account isn’t.

But when I envision who I want to be, and how I want to get there, I realize that time, money, and networking are — like willpower — just tools.

What matters is what I’m using those tools to build.

I didn’t have that clarity when I quit my day job. I had a vague plan — or at least I thought I did — and then reality intervened and that plan dissolved. That’s a story for another day. But as a result of that change, I spent the past year floating adrift without committing to a course of action.

I’d say a year in the wild — or a year of endlessly refreshing Twitter — is enough.

It’s time to get back to work on building the me I want to be.

There’s still time.

Now I just need to use it.