How I Started and What I Gave Up to Be a Freelancer

Six months ago, in early March 2019, I quit my job to pursue full-time freelancing. Here’s how I conquered my fears.

Daisy Quaker
The Startup
8 min readSep 30, 2019


Photo by Rodion Kutsaev on Unsplash

It began as a seed of an idea roughly six months before. I felt stuck. My career had started to feel like it was hitting a plateau. And although I liked the people I worked with (well — some of them, at least) I didn’t feel like I was learning or growing as much as I wanted to.

Most troubling of all, I felt that a big move or a shiny new job wasn’t going to get rid of this gnawing feeling that I was unhappy at work. A new job would be helpful and offer a change of pace, but it would mean trading my time. I wanted to own all of my time, I realized.

The idea of not having a safety net overwhelmed me at first

I was nervous. I had not invested enough in building my visibility and professional brand online. I didn’t regularly pen articles to showcase my skills nor talk about my work. I had a small following on social media, mostly made up of friends and a few random connections. I didn’t have a roster of speaking gigs to point to, nor big-name employers to attach to my name.

I had none of the things I assumed freelancers should have in order to be successful. But I felt compelled to start down this new path.

I gathered my guts, and on a chilly February afternoon, shortly after the lunch hour when I knew my boss would be in his office, and everyone else would be slowly making their way back to their desks, I peeked my head in, sat down, and told him I planned to quit.

Photo by Victoria Heath on Unsplash

A month later, I opened my laptop and started my new role as a digital marketing freelancer. And you know what? Aside from a few freakouts, it’s been better than I predicted. If you feel like this is something you’d like to do, here are the steps I took to make the leap. They might help you, too.

First off, why do you want this?

What’s driving this desire? What is it about the freelance lifestyle that inspires you?

Knowing why you’re doing this is vital because it will give you direction while everything else feels in flux. It will also help you build a business that fits your goal.

For me, it boiled down to freedom. This goal became my compass. It guided me through the transition, and each step became a way of making progress toward owning my own time.

Fears are OK and healthy

I had several gremlins.

What would I do about health insurance, I wondered? Having dealt with Lyme disease for over two years at that point, I wanted to make sure I wouldn’t be chewed alive by medical bills.

A second fear involved retirement. As an employee, retirement was something that would take care of itself. When you go into freelancing, you kiss retirement packages goodbye, along with all other benefits.

There was also the reality that I couldn’t hide anymore. It took a while to identify that fear. It had many disguises. Being a freelancer meant I would need to reach out, email, speak up, and write about my work. I would need to be seen to get hired. I hadn’t written about my work for at least four years. Where would I even begin?

I faced the gremlins by identifying my fears and tackling them one at a time. I set appointments with financial advisors and bookkeepers. I asked them who they would recommend I should also meet with. I made a list of all the things I wanted to do before I quit. A notebook worked fine for this, and each week I tackled one item on the list. The list was long, and in the end, not everything was crossed off. But it made my gremlins something I could reach around and hug. Hug and squeeze until they became a lot smaller.

I also promised myself that by the following summer, I would work from the beach. Something I couldn’t do at my job. The visual and setting a date made everything feel more real to me. My goal became months, not years.

Photo by Felipe Guandelini on Unsplash

Build a cushion, save money

I put half of my paycheck into my savings account for the six months before I quit. I had a small savings account. I worked my way up to putting half my paycheck into savings automatically. Thirty minutes with HR, and it was set up. This one move helped me grow my savings account significantly. Had I known how well this mental trick worked, I would have done it sooner. There’s a reason most financial advisors recommend it: seeing less in your checking account makes you spend less.

Calculate your cost of living, then carve it down

Maybe you’ll make more, but I knew that while I got my bearings, I would be making a lot less. So I created a spreadsheet where I plugged in all my expenses. Then I organized them into three buckets: Essential, Nice, and Luxe Life. Essential represented what I needed to make each month at a minimum. This would be my base salary, plus a commission on what I sold that month. It’s a little kooky, but it works.

I also whittled down what counted as essential. I moved out of my apartment to save on rent. I unsubscribed from a lot of shopping emails and cut back on eating out. All pretty doable, plus it made my savings grow quicker.

Start attending networking events and introducing yourself

I had an aversion to doing sales work. I felt like people would find me pushy and run away as soon as I asked if they were looking for digital marketing help. They didn’t.

Photo by HIVAN ARVIZU @soyhivan on Unsplash

I landed my first client about three months before I handed in my notice. I kept the client for six months, which helped me grow my savings and eased the transition into being a full-time freelancer.

If you want to pursue freelancing sometime soon, sign up for a local networking event, bring your business card, and introduce yourself to people. Ask them how they run their business, and if it feels appropriate, mention you take on clients. Suggest meeting up for coffee to follow up on some of the ideas that come up in your conversation.

Accept that you will have to make trade-offs

Owning your time comes with sacrifices. Some I expected, others surprised me. It comes with the territory. Here are the challenges that took me off guard, but actually turned out to be blessings in disguise:

Seasonality > Stability

For me, for now, being a freelancer is not as stable as having a steady paycheck coming in every two weeks. I don’t know what my tax bracket will look like at the end of the year. Some months I’ve done well, and some months I haven’t. The first year, this is inevitable.

I’m learning to embrace seasonality. I don’t want to be busy all the time, and too much freedom leads to boredom — it’s a balance. Accepting the highs and lows of freelancing has helped my emotional and mental health. When I have a lull, I use the opportunity to take stock of what I’m doing and envision where I want to take things next. It’s also a chance to work on projects that will diversify my income and build my business.

The discomfort of learning every week

I’m not competent as a freelance business owner yet. I still have a lot I’m figuring out. Each week, I’m doing something that I wasn’t doing the week before, and boy do I wish I could go back and fix that email, proposal, or meeting I had last week. But I can’t.

Even my version of what success looks like has changed. It’s not just a monetary amount. It’s the types of projects I get to do and who I’m collaborating with. It’s also about what I’m learning, and how much growth I’m getting from each new experience.

It’s been helpful to not beat myself up over an unsuccessful pitch and to keep moving forward after not getting that callback. Eyes ahead.

You have permission to do whatever you want — use it

A few months into freelancing, I had a realization:

“It’s my business, I can build whatever I want.”

It was liberating.

Whatever gets you jazzed, build with that in mind from day one. I decided I didn’t want to be the kind of freelancer who is chained to her desk, never investing time in hanging out with the people she loves or taking time off. So my schedule became Monday through Friday, nine to five.

I also took a long vacation to see my family and to visit my boyfriend’s family. Five weeks in total spent travelling this year, and it’s only September. Irresponsible, perhaps, given how young my business is — but taking things slow during this first stage of building a new business gave me much-needed clarity on how to move forward with care.

Write yourself a permission slip, if it helps. I’m not kidding — it helped me deal with my guilt over not being productive all my waking hours.

Photo by Daisy Quaker

Stress less over making money

There have been times I’ve thought about how nice it would be to not worry about making a sale or tracking my billable hours. There have been times I’ve thought back to my job before freelancing. How safe it felt.

I don’t know what the freelancing vision looks like for you, but for me, it has been the ability to choose exactly how I spend my time. And that has been pretty wonderful. The perfect day starts with a morning yoga session followed by walking to everything I can (instead of paying for an expensive gym membership). And most importantly, as I got to savour just this morning — breakfast with my partner before we both start our days.

I did it — you can too if you want to

If you work at a job that feels soul-sucking, you don’t have to stay there. Not everyone has the luxury of quitting when they want to, of course — I know that. Quitting wasn’t a luxury for me — it was scary. But there were a couple of things that made it less scary, and hopefully reading this can make it a little less scary for you, too.

And yes, I did get my day at the local beach.

Photo by Daisy Quaker

I’m sharing what I learn each week on this freelance biz path via email. It’s like a tête-à-tête. Sometimes it’s inspiring, other times there’s a cautionary tale or a riff on crucial learnings of the week. But always 100% heartfelt.

Interested? Signing up is a pretty good place to start.



Daisy Quaker
The Startup

Digital content marketing freelancer. I work with startups and small to medium-sized businesses. Web: ->Grow with me: