2019 Year in Review: Freelance Wins, Disappointments, and Goals

Dec 31, 2019

I’m just now realizing that I haven’t actually written a blog post since last year’s recap. Yikes.

Much of my radio silence is owed to the fact that I’ve been more focused on other efforts and resources (like my weekly newsletter and Facebook community).

But, there’s a big part of me that misses blogging regularly, and I definitely need to be better about investing some time and sharing information and advice here. Perhaps you’ll see that on my list of objectives for 2020, huh? How was that for a dramatic teaser?

Anyway, I’ve said it before and I’ll recite the same caveat again: I struggle with these year-end recaps. I’m all about being transparent (yep, even about my income), but I think these reviews can easily lean more toward, “YAY! LOOK AT ME AND HOW WELL I’M DOING!”

The thought alone makes me feel icky. But, I always dedicate some time to reflection and intention-setting at the end of the year—and, I figure if I’m going to do that anyway, I might as well share it with you, right?

Plus, I wish I had this sort of visibility into the ups and downs of the freelance life when I was just getting started.

I’ve probably justified and explained way more than I need to. So, let’s cut my rambling short (well…err…short-ish) and get into the good stuff.


Freelance Recap: 2019 By the Numbers

Before we jump into all of the highs and lows, here’s a quick look at some key digits from the past year.

Not all of my numbers from 2019 are in yet, so some of these are estimates. But, I think they’re still helpful—and they shouldn’t end up being that far off from reality!

  • Number of Years as a Full-Time Freelancer: 5.5
  • 2019 Total Income*: ~$120,000 (I haven’t had a chance to do the detailed calculations yet!)
  • 2019 Expenses: ~$9,500
  • Number of Clients I Worked With: 24
  • Clients Who Were New This Year: 7

*Remember when I said I was all about transparency? I mean it. This is an estimate of my total gross income for the year, but it’s not technically all freelance income. There are two part-time W-2 positions included in here.

Until April, I worked as a part-time staff writer for The Muse and was considered an employee rather than a freelancer. I’m also adjunct faculty at a local technical college, which is another W-2 position.

Things That Went Well in 2019…

In all honesty, 2019 feels like a bit of a blur. When a year moves so fast, it’s easy to move into the next decade (uhh…what!?) and just skip over celebrating your wins.

But, in thinking back, a lot of great things happened in the past 365 days. So, let’s dig into a few of the peaks, okay?

I felt better about my work-life balance than I ever have.

When it comes to cold, hard cash, this was the biggest year in business I’ve had (more on that in a little bit). But, while I’m proud of those digits, I’m even prouder of the fact that I feel like I really mastered the art of working smarter and not harder this year.

I made a conscious effort to set boundaries, carefully evaluate opportunities, and focus on working exclusively with clients who understand my value.

The result? My highest income to date, yes. But also more time to relax and even focus on non-career-related things that I love.

Here’s just one example: A little over a year ago, I joined a choir in my community. I’ve become even more involved with that group, and it’s seriously been such a joy to spend some time each week making music with a bunch of talented vocalists. Below is a photo from one of our recent Christmas concerts.


I had my byline printed by The New York Times.

Yes, you read that right. The New York Times. I’ve admired the Smarter Living section for quite some time, and I finally gathered some courage to pitch the editor (after a hefty amount of Twitter stalking).

Much to my surprise, he got back to me. And, he ended up commissioning me to write some advice for the “Tip of the Week” blurb that appears at the bottom of the weekly Smarter Living newsletter.

It was only a couple hundred words. But, for a small-town Wisconsin writer who only got started a few years ago, it felt like a major accomplishment.

As if that wasn’t cool enough, my advice was just re-published as one of the top nine tips (gah, out of over 50 tips!) from the entire year. You can read it right here. Seriously, how amazing is that?


I had my biggest financial year ever.

I already hinted at an impressive year income-wise, so I’m sure you figured this would appear in my highlights somewhere.

At an estimated income of around $120,000, this is the highest-earning year I’ve had since starting my business. As strange as it can feel to blatantly share my income, I’m proud of that.

However, I do want to mention a couple of things. First, I think it’s way too easy to look at your income as your only benchmark for success as a freelancer. While it certainly can be a great indicator of how things are going, it almost never tells the whole story.

Did you have better work-life balance? Did you find clients who are more suited to your interests and expertise? Did you develop a new skill? Those are all indicators of a wildly successful year, too.

Secondly, I never want to seem overly aspirational. Earning over six figures as a freelancer is amazing, but it’s certainly not something that happened overnight (seriously, I started out earning pennies). I’ve been at this for years, and the money situation hasn’t always been like this.

Don’t believe me? Here’s a peek at my estimated total gross income every year that I’ve been in business:

  • 2014 Income (half a year, since I started my business in July): $5,300
  • 2015 Income: $32,000
  • 2016 Income: $80,000
  • 2017 Income: $102,000
  • 2018 Income: $98,000
  • 2019 Income: $120,000

I found a passion for higher education.

Toward the end of 2018, I did something that made me a little uncomfortable: I accepted an adjunct faculty role as an Employment Advisor at a local technical college.

I was excited, but the idea made me a little uneasy. Would I have enough time? Would this make my identity as a freelance writer seem confusing or illegitimate? I only wrote about career advice for years…so did I really have the expertise these students needed?

I think being nervous about this change was totally normal, but I’m pleased to report that I’ve really thrived in this position.

A few hours each week, I get to put on some real pants (gasp!), leave my house, and work with students on a variety of employment and job search challenges.

It’s been so rewarding, and surprisingly I’ve found a real passion for higher education. Who knows…maybe one day I might even pursue a master’s degree myself.

I invested in my mental health.

I’m almost embarrassed to admit that, prior to this year, I had never been to therapy.

It’s not that I had anything against it. I just never thought it was something that could be helpful to someone who wasn’t in a major crisis.

I was wrong. After experiencing some major stress toward the beginning of the year (I promise, we’ll dig into that in the next section), I decided to give therapy a try and see if it could help me find better ways to cope with some of the anxieties that I’m sure we all deal with.

Seriously, it was a huge help, and I actually started to look forward to heading into those sessions every two weeks. By working through some things, I felt way more collected and had some tools to recognize the things that I could control—and the things that I was just needlessly stressing about.

I would happily encourage anyone (whether they think they’re struggling or not!) to take some time to prioritize their own mental health and even talk to a professional if they think they could benefit from doing so. I was surprised by how much it helped me in both my personal and professional life.

I took some amazing trips.

I love any reason to take a break from my normal routine and explore new places or return to spots I love.

This year, I took full advantage of the flexibility of the freelance life and went on numerous amazing trips around North America. These included:

  • New York City, March (we even crossed something off my husband’s bucket list by seeing the Red Wings play the Rangers at Madison Square Garden)
  • Las Vegas, NV, May
  • Georgia and Alabama, June (it was ridiculously hot and humid, but worth it to visit some of our best friends who moved there)
  • The Porcupine Mountains, upper peninsula of Michigan, July (this is one of our favorite places on earth, and we go every year)
  • Banff National Park and Yoho National Park, Canada, August (seriously, go if you get the chance—it’s gorgeous)
  • Duluth, MN, November (my husband and I always take a little fall weekend getaway here)

Plus, we took four different trips to lower Michigan to visit my husband’s family. Whew!

Next up? We’re hoping to cross some more international travel off of our list. Let me know if you have a place you’d recommend!

Things That Didn’t Go So Well in 2019…

Life isn’t always sunshine and rainbows, right? This year treated me exceptionally well, but like anybody, there were a couple of valleys I had to trudge through. Here are a few of the memorable ones.

I started the year feeling totally overwhelmed.

I’ll be honest: The start of the year was pretty brutal for me.

I was just getting into the swing of things in my adjunct faculty role at the college, and balancing that commitment with my client work proved challenging. I also bit off way more than I could chew in terms of projects, and ended up completely overwhelmed.

I’m not exaggerating. We’re talking a full-blown panic attack sort of overwhelmed. Not fun.

But, that was the breaking point I needed to realize that I needed to make some serious changes and avoid packing my life so full of work commitments. I managed to get that in check after the first three months of the year, and then felt much more balanced for the rest of 2019. Whew.


I had to make some difficult business decisions.

There’s nothing like a series of panic attacks to make you seriously evaluate every single commitment and obligation in your life.

When I finally came to the realization that I needed to shove some stuff off of my plate, I knew I needed to make some really tough decisions. As a freelancer, it’s so counterintuitive to think about letting go of any work—you figure you should hoard it while you can get it.

But, at the very end of March, I made the incredibly tough decision to leave my gig as a part-time staff writer for The Muse. I had worked in that position for a little over three and a half years, loved the team, and was so proud of everything I had created.

However, it was also a huge commitment in terms of time and energy, and I knew that wrapping up that position would not only mean less work each week, but also one less email account, less weekly meetings, and less instant messages. It would free up time, while also reducing a lot of the mental clutter that was stressing me out.

So, I put in my two weeks notice and wrapped up that long-standing position in April. It was a heartwrenching decision, but looking back now, I know it was the right one for me.


I struggled with some priorities.

I had some major wins this year, but I also fell short on some bigger-picture goals that have been looming in my mind for quite some time.

For the past couple of years, I’ve wanted to invest even more into this passion project of providing resources and advice for fellow freelancers. Specifically, I really want to launch an online shop where I can offer templates, worksheets, and more.

I definitely made some strides toward making that happen this year, but I wasn’t able to cross the finish line on actually rolling out the shop. It’s just so gosh darn challenging to prioritize personal goals like that (especially when they’re currently unpaid!) over client work, but I want to be better about that in the coming year.

What I’m Looking Forward to in 2020…

It’s a brand new decade, and I’m kicking it off with a refreshing sense of optimism—mostly because I know I have a ton of exciting stuff in store. Like what? Here’s a sneak peek.

I’m becoming a mom (whoa).

Did you miss the big announcement? My husband and I are expecting our first baby in May of 2020.

We’re so excited (and admittedly slightly terrified) about becoming parents and bringing life into the world.

Navigating the uncharted territory of breaking the news to my clients and planning my impending maternity leave has been an interesting challenge—which I’m sure will provide lots of fodder for future blog posts.


I’m making more time for the work that excites me.

I’ve been at this whole freelance thing for five and a half years, and I feel fortunate that I genuinely still enjoy what I do.

But, even so, I’d be lying if I said it doesn’t feel like a job most days. If you do anything for long enough, the shine wears off and it can easily become monotonous.

I’m trying to pay more and more attention to what work excites me, and I know that I always feel energized by this passion project right here. So, I really do want to sink more time into my personal blog, newsletter, Facebook community, and yes, even getting the shop launched in 2020.

Is it overly optimistic to plan on doing that in the same year that I have a baby? Probably. But here I am speaking it into existence anyway.

I’m starting the home-building process.

About five and a half years ago (yep, right around the same time I started my freelance business), my husband and I bought our first home.

It was always intended to be our “starter” home…somewhere we’d be for a year or two before moving on.

Well, we’re creatures of habit and we’re still there. However, we also own two and a half acres of wooded land just outside of the town we live in. We bought the property with the intention of someday building our dream home there, and that idea is finally becoming a reality.

As of right now, we aren’t planning to break ground until the spring of 2021, but we’re starting the process of working out finances, talking to builders, and drawing up some initial plans. It’s so exciting (and intimidating) to finally have that far-away dream seem like it’s within reach.

Plus, don’t these adorable doggos deserve a cozy house in the woods? I thought so.


So, How Was Your Year?

There you have it—an in-depth look at some of the things I had going on in 2019, and some of the things I’m aiming for in 2020.

Now, it’s your turn. These year-end recaps always feel self-centered enough, so I want to know how your year treated you too.

Drop me a comment below with some of your own highs and lows from the past year. And, if you’re feeling extra ambitious, loop me in on some of your ambitions for the upcoming decade!

I have a feeling it’s going to be a great one.

Want to keep up with how this year goes for me? Outside of this blog, there are a few other places you can keep in touch (yep, this is a shameless plug):