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I Left My Full-Time Job to Start a Business. Here’s What I Would (and Wouldn’t) Do Differently

2018 was a pretty exciting year in my life. I visited eight states. I moved into a cute little townhouse. I paid off my biggest student loan. Oh, and I left my full-time job to launch and grow Lightning Media Partners.

As I explained in this blog post, the leap was a long time coming. A few years ago, I started actively seeking freelance writing clients to earn extra income. I joined Upwork and found a couple of steady, recurring projects. They didn’t pay the bills, but it was money I didn’t have before.

At first, my side hustle let me do the “fun” stuff I couldn’t justify while paying off credit cards and student loans — fancy restaurants, weekend vacations, new gadgets, etc. Then, my life took an interesting turn: I got divorced, and suddenly I had to pay rent on a new apartment plus mortgage payments while my ex and I tried to sell our house. A new freelance client helped me do it.

After the house sold, I didn’t “need” my side hustle the way I did before. But I didn’t want to stop. I loved the thrill of chasing new clients and landing ongoing contracts. I loved being able to make sizable dents in my debt, and still having money left over to put in savings.

I realized that the only limit to my freelance earning potential was my own capacity to take on new work. Working for someone else full-time wasn’t going to give me that kind of growth, so around this time last year, I made a pact with myself to save up, quit my job, and make freelancing my primary source of income by the end of 2018.

With the help of my very supportive partner, I conceptualized and soft-launched Lightning Media Partners. His background in SEO and marketing helped round out my editorial skills, so we could offer a fuller range of services to clients. What started as solo freelance work doing occasional blog posts and copy edits evolved into a two-person team of polished, ambitious content marketers.

I started reaching out to connections and letting people know I was looking to grow my new agency, and the floodgates of opportunity opened. In September, I was earning enough to drop to part-time at my corporate job, and shortly after that, my partner was able to quit his full-time job, too.

What I’d Do Differently

I’ve learned so, so much in these last few months of self-employment. If I had to do it all over again, there are a few things I’d approach differently:

I would market myself more aggressively.

If I had put my current level of effort into client acquisition when I started freelancing, my whole timeline probably would have moved up by a year or two. My priorities and goals were different back then — my 2015 self wasn’t necessarily expecting to earn a living as a freelancer. Still, I might have been able to get out of of debt sooner if I’d done some more business development!

I wouldn’t undervalue myself.

Like many new freelancers, I had no idea what “fair” pricing was for content work. I was also desperate for clients, so I lowballed myself and worked for far less than I could and should have been earning based on my skill and experience level. I later realized that many clients were willing to pay more than what I was charging — I just had to confidently ask for it and back it up with my past results.

I would have planned better for taxes.

In 2017, I was hit with a massive tax bill that I wasn’t quite prepared to pay. I had been saving a portion of my freelance checks all year for self-employment taxes, but it’s reeeeeally easy to start dipping into that savings account when your laptop crashes or your dog has an expensive vet visit. If I’d made quarterly payments instead of waiting to pay it all at once when I filed my taxes, I’d have been able to manage that money better (and yes, I learned my lesson for 2018).

What I Wouldn’t Change

To be honest, there isn’t much else I would have done differently in getting to this point. Here are a few things I’m glad I did in my entrepreneurial journey:

I waited to leave my job until I could fully pay my bills with client work.

I definitely wasn’t out-earning my full-time corporate job when I left, but I had enough steady work to cover my basic living expenses plus self-employment taxes. Could I have left sooner and stretched my budget? Probably. But I’m glad I didn’t.

I asked for help.

I was burning out HARD in the months before I left my job because I was trying to do everything by myself. Delegating some work to my partner helped, but what really freed us up to focus on our strategy and growth was hiring a few talented freelancers to take on our spillover projects and administrative tasks. It’s a tough paradox to accept, but spending money to hire help lets you go after bigger contracts and earn more in the long run.

I trusted whole-heartedly that I could do this.

Fear and self-doubt stop so many would-be entrepreneurs from going after their dreams. I wasn’t going to let myself be one of them. I knew what I was getting into and worked hard to prepare for the challenges ahead. Because of that, I had — and still have — the utmost faith that I did the right thing for myself and my career.

I chose to live by my own definition of success, and I will keep defining it for myself as Lightning Media Partners continues to grow in 2019.

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