Six Things I Learned In My First Freelance Year

At this time last year, I walked away from my steady, reliable job. I was excited. I was terrified. I wrote about it here. Inspired by Glennon Doyle’s Untamed, I set out to create the “truest, most beautiful life” I could imagine. 

Although I can’t say I achieved that lofty goal, I have kept my little business afloat for 12 whole months. Kristin Hanson Writes has grown beyond anything I could have expected in its first year. At the same time, I’ve been schooled in some of the less fun things about being your own boss. 

On this first anniversary of my “great resignation,” here are six of the most important things I’ve learned—and will continue to learn—about changing careers and striking out on your own.  

Asking for help opens lucrative doors.

Long before I took the plunge into full-time freelance work, I began working with a career counselor. She encouraged me to make a list of people I knew who had made a similar transition in their careers. Some of them I knew well, like a former boss. Others were acquaintances at best; a friend of a friend, or someone I met at a conference years ago. But when it came time reach out, I wasn’t comfortable making the ask. I don’t like asking for help, and I really don’t like feeling rejected or ignored. My career coach simply replied, “What do you have to lose?” I didn’t have a good answer, so out the emails went. 

To my surprise, each of the eight people I wrote to wanted to speak with me. These are all busy folks, but they didn’t hesitate to spend an hour (and sometimes more) on the phone, sharing their warnings, recommendations, and encouragement. Months later, to my even greater surprise, a few of those people reached out to me with connections to job opportunities. Putting aside my discomfort—and my fears of a bruised ego—has literally paid dividends. 

Be professional, not a pushover.

When you run your own business, you need to put your interests first, always. Because I was new to freelance work, and I’m someone who in general likes to be liked, I made a lot of early mistakes in this area, including: 

  • Underestimating the time some projects would take and, therefore, undercharging clients for the quantity and quality of the work I performed. It sucks to be underpaid, and it’s worse when you know you caused the situation.
  • Failing to realize the time a project would take and agreeing to be paid in full upon the completion of the project (instead of requiring a deposit and interval payments). It sucks to do thousands of dollars of work only to wait weeks (or months) to be paid because your client drags out the review process. 
  • Completing work that’s outside the scope of a contract or moving forward on projects despite the client being behind on payment. It sucks to feel like you’re being taken advantage of—but at the same time being afraid of alienating a client when your business is so young.  

These situations have been painful, but they’ve been great teachers. Although I haven’t completely shed my “people-pleaser” personality, I am more professionally assertive (and writing much better proposals and contracts) with a year of experience under my belt.  

Administrative work is *work.* Don’t do it for free.

The beauty of freelance work is being your own boss. The curse of freelance work is … being your own boss. I am responsible for everything that surrounds the core work I do—business development, meeting scheduling, proposal writing, contract writing, billing, tax preparation, and more (a.k.a. overhead). When I worked in-house, these tasks were out of sight and out of mind, handled by other people or departments in my organization. I had no idea how much time administrative work would take (surprise! it’s a lot), but I learned quickly. 

About a month into my full-time freelance career, I noticed my hourly rate was far below what I calculated it to be in my previous roles. I decided to start tracking the administrative hours I spent on each project. I realized I was drafting several versions of proposals, responding to tons of emails, taking multiple calls and meetings, and I wasn’t incorporating any of that time into my pricing estimates. I was doing a ton of work essentially for free. Armed with that knowledge, I began including these costs in my estimates. My proposals and contracts better reflect all the time I spend working for my clients, whether it’s putting pen to paper or picking up the phone.  

Taxes suck, and they’re worse when you work for yourself.

News to me when I started down this road: When you’re a freelancer, you get double taxed—income tax and self-employment tax. And, to avoid paying a penalty, you have to pay your taxes four times a year. It sucks, but it is what it is. 

Full disclosure: I have an ace-in-the-hole in this regard; my mom is an accountant. Before I officially launched myself as a business, I got a lot of free education (and, ahem, free help) on all things taxes. With her guidance, I’ve done a few things to make paying the man less of a pain, functionally and financially. (If you don’t have an accountant for a parent, a simple google search for “independent contractor taxes” or “freelance taxes” delivers *lot* of useful information.) 

For all projects, I estimate the tax that I will pay on that income and ensure it’s at least partially included in the price I quote. Second, I take a certain amount of money out of each check and put it in a separate bank account from which I pay my taxes (trust me, this makes the bite at tax time hurt less than taking the lump sum out of your checking account). Third, I’m starting to pay my quarterly taxes online whenever possible (it’s a hell of a lot easier than schlepping to the post office four times a year and paying to send tax checks via certified mail). 

Get comfortable saying “no.”

Whether it’s imposter syndrome or fear of the unknown, it’s easy to enter self-employment with a scarcity mindset. There’s a strong drive to say “yes” to every job in the interest of business-building or getting a paycheck. I still feel that urge sometimes, but I also know the consequences of saying “yes” when you shouldn’t: frustration, stress, and burnout. Saying “no” is easier when I keep three questions in mind:

  • Is this a client I want to work for? I like having control over who my “bosses” are. Before I onboard a new client, I try to do due diligence through research and conversation to determine whether this is someone I’d be happy to support. If they’re not, it’s a “no.”
  • Is this a project I would enjoy? I’m capable of doing a lot of things, but I don’t necessarily like them all. If the work doesn’t challenge or interest me, or seems like it’d be a big pain, it’s a “no” (or at least I make sure the contract’s terms make the job worthwhile). 
  • Does this project have the flexibility I need? I chose freelance work in part because I wanted to parent my toddler (and soon-to-arrive newborn) with less stress. If a client has strict requirements that don’t allow for flexibility in an emergency (like a random toddler fever or daycare shutdown), it’s a “no.” 

Change the way you measure yourself.

In our society, we’re trained to climb ladders. We’re addicted, even as little kids, to external validation. If and when you decide to step off that treadmill, it’s disorienting. There are no more ladders, and—at least in my line of work—relatively few opportunities for external validation. No promotions or job changes to share in a LinkedIn post. Few, if any, awards to aim for or celebrate winning. In many cases, I’m contractually prohibited from sharing my work, whether it’s a great white paper I put together, a multibillion-dollar proposal I crafted, or a popular trade magazine article I ghostwrote. 

Freelance work (especially in a pandemic) can be lonely. Working for yourself can be draining. It’s easy to start questioning your decisions and doubting your worth. Over the past year, I’ve had to revise my definition of “success:” How can I feel worthwhile without having a new title, office, raise, or award to announce to the world? How can I feel valuable when there’s no one to reassure me I’m doing a good job? I don’t always have satisfying answers to those questions. But going back to the beginning and asking myself another question helps: When I decided to make this drastic career change, what did I want to gain—and am I getting it?  

I wanted autonomy. I wanted less drama. I wanted more of the work I like and none of the work I hate. I wanted the freedom to be the parent I know I can be. And I wanted to keep writing. 

By that measure, it’s been a very successful year. 

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