Freelancer Spotlight: Krista Doyle on How to Build a Content Empire

In January 2019, I quit my promising, cushy full-time job at a growing tech startup to join the ranks of the full-time freelancers with my content business, Content Is Queen. That might sound crazy, but I’m not the only one. According to Forbes, the number of Americans freelancing has increased by 3.7 million people since 2014. Workers are jumping the 9-to-5 ship in droves in hopes of making it to the lifeboat that is a flexible, exciting, rewarding freelance career. 

Over the past year, a lot of people have asked me for advice on the “What, Why, and How” of quitting your job and starting your own business. Lucky for you, reader, I’ve gotten these answers down pat and can pass the info along to you. Interested in becoming self-employed? Here’s how I made it happen.

Why I Decided to Work For Myself

To be frank, I think I’m a little bit of a control freak. As much as I loved my job and the company I worked for, there was something that freaked me out about having to rely on other people to look out for me and my career. It bothered me that, for the rest of my working life, I was going to have to trust other people, other flawed human beings, to decide how much money I’d make, what job title I’d have, what work I’d do, and when I’d do that work. They’d decide what time I needed to be in my desk chair and when it was acceptable for me to leave that desk chair. 

I liked the idea of working for myself because, in that case, at least I would be the one solely responsible for my success (or lack thereof). How much I grew and how much I earned would be directly related to how much effort I put in, not whether or not there was room in the budget that year for a raise from whatever company I happened to be at.

TL;DR – I highly value financial stability and security (likely a result of my less-than-stable 20s) and that was probably the biggest motivator in wanting to work for myself.

What Steps Did I Take To Begin? 

Step 1: I Made a Game Plan With My Wife

Not your typical date night conversation, but yeah, my first move was talking with my partner about this giant life decision I was making. She was very supportive and we both decided that because we were newly married, living within our means, and didn’t have kids, it was the right time for me to take on a little more risk. And since money problems are like, the Mayor of Divorce City, I was really adamant that we keep our finances separate for a while so that she is never footing the bill for my risky new job. 

Regardless of your relationship status, a game plan is necessary to make sure you know what you’re getting yourself into.

Step 2: I Took On Part-Time Freelance Work to Build a Client Base.

When I decided to start my own freelancing business, I had exactly $0 in my savings account and about $50k in debt (shoutout to Sallie Mae, girl, you wild!). I was in NO position to blindly quit my job and hope that potential clients magically appeared to give me money. So, I took on a few writing jobs on the side in order to build up a base of clients that made me feel comfortable enough to quit my job. 

To find these clients, I utilized local Facebook freelancing groups and the trusty ol’ network. Never underestimate the power of emailing a few trusted contacts and letting them know you’re open to freelance work. Someone ALWAYS knows someone who knows someone who knows someone. After I had three freelancing offers from clients who I knew needed my help for at least the next six months and covered all of my expenses, I felt safe enough to take the leap into full-time.

Note: To be honest, this step really sucked. The extra money was nice, but I spent a lot of nights and weekends being really stressed about the workload I had taken on. Ultimately, it was worth it because it allowed me to quit my job, but just know that it’s tough and is not sustainable long-term unless you enjoy working 80+ hour weeks. 

Step 3: I Had an Honest Conversation With My Company.

As I said, I didn’t hate the place I worked. I learned a ton during my time there and met people that I can’t imagine my life without. What’s to hate? As soon as I knew I had the ability to safely leave, I told my boss. I think I gave a month and a half’s notice. 

Having those conversations was scary as h***, but being honest allowed me to leave a job I cared about on good terms. They were very supportive and I even got to keep them as a client for a few months. Win-win!

Step 4: Consult an Accountant or Tax Professional.

Okay, this is something I did not do, but I really wish I had. Talking to an accountant or tax professional before you jump in head first to running your own business will help you so much when it comes to: 

• Knowing whether you should form an LLC or S-Corp;
• What items you need to track for tax purposes;
• What purchases qualify as tax write-offs;
• About a million other finance things I wish I had someone explain to me before I started.

I didn’t do this and tried to stumble through everything myself. It was a major headache and I wish I had just shelled out the money upfront to have someone help me and make sure it was done correctly.

TL;DR – Assess what you need in order to start and make a game plan. Build up a client base before quitting your job (unless you’re a richie). When it comes to your current company, go out in style, not down in flames. Talking to a money pro will save you a major headache.

How Do You Make It Work Long-Term? 

So, I’m actually still learning this. A year feels like a long time (especially in the thick of it), but it’s really not, and there are a lot of people who have been working for themselves for years and years and years. If they can do it, we can do it, right? 

Still, there are probably a few tips I can give you that have helped make running my business a little more sustainable: 

1. Don’t be afraid to hire contractors to help with major projects. I have a contract writer who’s worked with me for a year and I don’t know what I’d do without her! It can be tempting to try and do everything yourself, but knowing when to partner with other freelance writers has really helped.
2. Use accounting software like Quickbooks, Wave, or Freshbooks. I prefer Quickbooks because it integrates with a ton of other business tools and having it track purchases, invoices, receipts, mileage, etc is so very helpful. Plus, it makes me feel like a business wizard.
3. Project management tools will help give you structure that can sometimes be hard to maintain as someone who is self-employed. I use Trello to keep track of clients, projects, and contractor assignments. There is no greater satisfaction than moving a Trello card from “In Progress” to “Done”. 
4. Having benefits and retirement savings is still possible. Luckily, companies are innovating to keep up with the growing freelance workforce. Startups like Catch.co help freelancers get access to health insurance, set aside money for taxes, and build up a retirement nest egg. We really can have it all, you guys!
5. Always be planning. I started my business without having a longer-term plan in place and it really made things difficult for the first several months. I didn’t know what I was working toward and it really messed with my head! Having a plan in place for your business helps give you clarity and direction. What industries do you want to work with? Do you want to be a solo freelancer forever, or eventually hire a team? What annual salary would you like to eventually earn? These are types of questions that can help guide your actions today to get you where you want to be tomorrow. 

TL;DR – Hire help when you need it. Utilize helpful tools and software. Always have a plan for the future of your business. 

Since starting Content Is Queen last January, I have gone from solo freelancer to aspiring agency owner who manages a team of contractors and has hopes of building a successful boutique content marketing company over the next few years. My team and I have gone from working with a million different industries to narrowing our focus down to the travel & outdoor space and rebranding as Backpack Content to better meet that niche’s needs. 

Working for myself has been a wild ride so far. It’s been wonderful and terrifying and I’d be lying if I said I didn’t sometimes wish I was back in a more stable 9-to-5 job again. And maybe one day I will be, but right now I’m enjoying the ride.