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  • Writer's pictureLiz Breen

How I Knew It Was the Right Time to Go Freelance

Updated: May 10, 2020

I'm pretty much the Diddy of the blog world. I wait for you to forget about me completely, then BOOM. I bust back onto the scene.

It's been a while, huh? The past 7-odd months have seen a lot of change, the biggest of which being that I left my full-time job to pursue freelance.

Frankly, freelance is something that's been in the back of my mind for nearly 4 years now, and something I've come close to pulling the trigger on a few times before this past summer. But I never did. Something kept holding me back or diverting me. A full-time opportunity would present itself, and I would take it. And in those moments, I couldn't help but feel a little cowardly. Was I just playing it safe? I knew I wanted to make this move, so why wasn't I doing it?

Short answer: It wasn't the right time.

Years ago, I had a kind of serendipitous conversation with a man I'd never met before and have never seen since, who advised there was no such thing as the "perfect" time to do anything, and if I sat around waiting for things to be "perfect," I'd never get where I wanted to go. It's a conversation that (clearly) has stuck with me and one that I tend to agree with. But I would amend his statement to say that while your timing can never be perfect, it can be right.

Perfect timing assumes that a decision carries no risk, which isn't realistic. Right timing, on the other hand, assumes that risks have been identified and mitigated as much as possible.

For me with freelance, the right time meant I had done a few things:

1) I'd taken advantage of what full-time has to offer.

I think that freelance work often gets overly romanticized while full-time work gets unfairly demonized. Does freelance life offer things that full-time doesn't? Certainly. But the same is true of the reverse, and especially as a young person in a creative field, I think it's important to understand how putting in your reps at a full time job (or jobs), especially right out of school, can benefit you in the long-term, even if your ultimate goal is to leave the world of 9-5s.

Yes, full-time jobs often offer things like health care and 401k matching that freelance doesn't. But more than that, full-time jobs (good full time jobs) offer mentorship.

As a freelancer, I don't have a whole lot of room to screw up. Clients expect high-quality work, and if I were to deliver anything less than that, they would simply drop me and move on. When I was coming up through the full-time ranks, though, I had bosses who would sit down with me, talk me through the work and show me how to do it better. When I could do it better and do it better consistently, I was rewarded with bigger opportunities. At times, some of these opportunities were well beyond my current skillset, but that was okay. Because even if I failed, I still had the larger creative team to fall back on; even if I failed, my bosses knew there were other, more experienced people on the project who would deliver. They were just being good mentors and giving me a chance.

Now, as a freelancer, there aren't a whole lot of "chances" given. There are jobs I'm being hired to carry out, and the client needs to know I can deliver. Which brings me to...

2) I'd built the portfolio.

The world is flush with freelance opportunities. Some of these opportunities are really exciting, others are essentially creative clerical work. Not only is one a whole lot more fulfilling than the other, one is a whole lot more financially tenable than the other. And at the risk of repeating myself, clients aren't going to give you the juicy, high-paying stuff unless they know for certain you can deliver. AKA a couple of spec pieces for a college class probably aren't going to cut it.

Luckily, my time in the full-time world and the opportunities I was afforded there gave me a solid portfolio of work, work for real clients who paid real money and expected some real results to come from it. And knowing that something was real -- that there were stakes involved -- is important to a potential freelance client. Moreover, the work my portfolio features some client names I wouldn't have been able to work with had I not been full-time (at least not before many, many years in the freelance world), working on behalf of an agency they trust.

3) I'd made the connections.

Snagging those big-name clients as a freelancer has come down to my portfolio and my connections. Big-name clients don't hire freelancers often, and when they do, trust plays a big role. So it's helpful when someone on a client's internal team can recommend you.

I've had the opportunity to work with some pretty incredible people at each full-time job I've had thus far, and many of them have gone on to do even more incredible things. I haven't even been freelance for 6 months now, and I think I've reconnected with at least one person from every one of my former jobs and they've either given me work through their company or passed my name along to someone they know at another company who is in need of a good freelancer.

4) I knew my numbers.

Before I made the jump, I did the math. I looked at my expenses, saw how much I would need to make each month to break even and determined if that was feasible, given my assumed day rate.

And I didn't assume I'd be working every day, either. My estimated take-home was calculated based on 10 working days a month. I've (luckily) always worked more than 10 days thus far, but I'm glad I was conservative in my estimate. It's taken a lot of the anxiety out of finding work and allowed me to actively pursue the kind of projects I'd like versus taking the aforementioned "creative clerical work" out of desperation.

5) I'd brushed up on the business-side.

I'm running a business now. Sure, it's a business with one employee (me) but there's a lot to understand in terms of bookkeeping, taxes, etc that I had to educate myself about.

6) I have worthwhile ways to fill my down time.

Because there is a lot of downtime. Much of my work is now remote, and without the distraction of meetings and office snacks and other coworkers, it's amazing how much I can get done in only a few hours.

While I could just watch YouTube videos of people falling for the remaining hours and my business wouldn't suffer for it, my personal growth would definitely be stunted. Though freelance has been a goal of mine for a while, it's not the ultimate goal. I'm young, and there's a lot more I'd like to do and accomplish. Freelance is only the next step in my journey.

Eventually, I'd like to have original content account for at least a portion (if not all ) of my income, so in my downtime, I'm often working on my own stories and sending work out to publications. And even then, most of my work days end around 4, which is around when my husband picks the baby up from daycare, meaning that's another hour+ I get to be with the family, another incredibly worthwhile way to spend my time (or so they tell me...).


Long story short, I'm so glad I finally made the jump and went freelance. It took 4 years, but they were 4 necessary years that (I hope) set me up for success in the long-run.

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