4 Lessons I’ve Learned Since Being My Own Boss for Three Years

That said, freelancing wasn’t a cake walk from day one. Over the past few years, I’ve learned a lot, made mistakes (still do!), and grown my business more than I ever could’ve imagined. In honor of my third freelance-aversary (yes, I actively celebrate this day), I’m sharing some of the best lessons I’ve learned since becoming my own boss. Whether you’re looking to go out on your own or want to finesse your business, I hope the lessons below will help you pursue a career that you love:

Diversify Your Revenue Stream

ICYMI, a full roster of dream clients doesn’t happen overnight. Finding clients and building your relationships takes time, and I’d be lying if I said every client I have came easily. That’s exactly why it’s so important to diversify your revenue stream — especially when you’re starting out. Sure, you take the leap of faith to follow your dreams and pursue a career that gives you meaning, but you’re also here to make money. Instead of sticking to your dream work and settling for nothing less, figure out how you can market your skillsets differently.

For example, I might prefer interior design and lifestyle writing, but I also fill my calendar with SEO articles, branded content, ghostwriting, media consulting, and even some social media work when I was first starting out. (I also took on writing that was outside of my beat, but came with a great paycheck!) That said, don’t put those diverse sources of income on the back burner as soon as you land that dream client. Nobody knows what tomorrow holds — hello, 2020 — so it’s important to give yourself some options.

Hold Yourself Accountable

Let’s be real: Mistakes are inevitable. While I’d like to think I do a lot of things right every day, I also do a lot of things wrong: I have typos, I forget to add an important piece of information to an email, and I’ll have so much on my plate that I submit a story to my editor a little late. I’m human, and I’m doing the best I can. That said, I firmly believe how you handle mishaps is more telling than the mistake you make in the first place. Take ownership of your mistakes, apologize, and move forward.

Have a client who gives you some harsh feedback? Take it in stride and think about how you can be a better you. (After all, they’re giving you feedback because they believe in you.) Running late on a deadline? Let your client know. Things happen, but having a good attitude will help you come out on the other side.

Be Bold, Be Kind, and Say Yes

As a freelance journalist, I’ve always thought your current paycheck is the key to your next paycheck. People want to work with people who are respectful, kind, eager, and can deliver — and that’s been my recipe for success. I muster up the courage to cold pitch editors, a topic that deserves its very own newsletter. I try to foster a positive, yet professional, relationship with my editors. I jump at (almost) every opportunity that comes my way and figure out how to balance it all. (My freelance philosophy is “make it work” a la Tim Gunn.)And, I try to do it all with enthusiasm and humility.

Quite frankly, I don’t subscribe to the idea of being pushy, rude, or demanding to feel like “a boss.” It feels archaic and, honestly, counterproductive. It doesn’t matter if you’re a journalist, career coach, or social media guru, a good attitude, enthusiasm, and an up-for-anything mentality goes a long way.

Find Your Normal

Once you take the leap of faith to become your own boss, you are in charge of everything from where to work to how you structure your days. However, all that autonomy can be a blessing and a curse. The first few months of being my own boss were hectic. I’d spend so much time jumping from a café with subpar WiFi, to a press event, to another café with subpar WiFi that I couldn’t focus.

One of the best things about being your own boss is that no two days look the same. Some days (okay, most days), I’m neck-deep in deadlines, while others are spent answering emails and submitting invoices. That said, it’s important to have some structure to your days. I know I’m more productive when I wake up early, head to a dedicated space (be it my dining room table or co-working office), take a mid-day break to exercise, and end the night with some social plans. Of course, finding the right structure requires some trial and error. Go ahead, switch up your work routine until you find a system that makes you your best self.

Hustler of the Week: Elyssa Goodman

I’ve always admired how much you do! You have a monthly non-fiction reading, an amazing photography portfolio, and are writing a book! How do you balance it all?

Thank you! The writer Ada Calhoun once said to me, if you want something done, give it to a busy person. I can do anything if I have a deadline. It’s all about time management, and it gets easier once you know how long things take you. It’s still a process I’m learning, too! There’s always room for improvement in anything we do.

What’s your favorite thing about being your own boss? Least favorite?

My favorite things are that I set my own hours: I take vacation whenever I want and I don’t have to ask anyone for it. I can take breaks whenever I want, I work on projects and stories that actually bring me joy, and there’s (hopefully) nobody who gets in the way of me doing my best work. I love that I get to do it myself, that I have built and continue to get to build something that’s honestly and truly mine.

My least favorite is that I also have to do it all by myself. (It would be great to have paid time off!) There are some days where it would really help to have, you know…some help. But even on those days, I take a deep breath and I say, “It will get done.” Because it has to. And that’s it! And you just keep going, keep building, keep giving yourself goals to achieve and make yourself happy. That, to me, outweighs anything I don’t like.

What is the best lesson you’ve learned since becoming your own boss?

You must be productive, but being productive has many forms. That comes from my dad. If you have downtime between gigs, it’s time to hustle to get more of them. Listen to what’s happening in the world and tune your ear to notice what stories are missing. Generate ideas. Read the publications you want to write for. Find out who the editors are. See what books, albums, movies, are coming out for you to write about. Things like that. And being productive also includes taking time off. If you work too much and get sick…you can’t keep working!

Working so hard like that actually ends up being unproductive. Since I started writing my book, I’ve made a conscious effort to take time off on the weekends because I know myself: I will just keep working, I’ll burn out, and then I won’t be able to work when I want to. So, I relax. I take time for myself doing something that brings me joy, and then I start again on Monday. Remembering to breathe, in all senses of the word, is important.

Give Elyssa some love by following her on Instagram, reading her blog, and checking out her website.

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