Penny For Your Thoughts: Things I Wish I’d Known Before I Quit My Job To Follow My Dreams

November 9, 2015  |  
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Lord help me if I see one more person on Facebook say, “I quit my job today to follow my dreams!” I want to virtually shake them by the shoulders via an inbox message that says, “Nooooooo, girl. Noooooooo! Wait! Turn around! Go back! Tell your boss that you were just kidding! Get your job back! Pleeeeeeeease.”

Eight years ago (or was it nine years?), I quit my magazine job as a junior editor to follow my dream of writing full-time for magazines. Sometimes I think it was the worst mistake I ever made.

Too often, stories of entrepreneurship are divided into two sections a) wild success or b) epic failure. But there are tons of stories in between and, chances are, that’s where you’ll be. At some point, maybe you’ll transcend from being in between to wild success, or you’ll plummet to epic failure. But you’d be wise to consider what it will feel like to live for many years—longer than what’s comfortable—in between.

That sounds depressing. And it is. But it’s not. (But it is.)

Rather than philosophize about why being in between is or is not depressing, I have drafted this list of things I wish I’d known from the in-between place. Some of us make it big when we strike out on our own, and some of us barely make it. But it seems the only people doling out advice nowadays are those who wildly succeeded and those who failed epically. I wish that someone who was holding down the middle ground had shared a word or two with me when I made the leap to entrepreneurship and non-traditional employment. So here goes.

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You have not arrived. And you will not arrive next year (or anytime soon or soonish, for that matter).

In fact, you may never arrive. This is a conundrum, because, in essence, you have arrived. Here’s list of some of the things that I’ve done since I’ve gone freelance: my work has been nominated for a National Magazine Award; I’ve hosted national events for O magazine; I’ve appeared on national morning shows to discuss stories that I’ve written; I was selected for a national leadership campaign for The Limited. If I die today people will talk about those achievements, I’m sure, but they’ll also lament the possibility of all that I could’ve been.

No matter how much you do, people expect more. In some folks’ eyes, we will never arrive. On occasion, my 85-year-old father will tearfully lament that he may not live to see me “be who I can become.” My mother has at times scolded me by saying “Every time you’re on the threshold of greatness, you wither.” When you are one of the folks who boldly attempts to chart her own path, you may come to feel that your path is always woefully short of the finish line. Take the Oscar-winning actress Jennifer Lawrence. Some people think that even she hasn’t arrived. Quentin Tarantino suggested that she has a little more work (and aging) to do in her career, saying, “I think she could end up being another little Bette Davis if she keeps on going the way she’s going.” So, be forewarned, the thrill of awards and achievements is fleeting. No matter what, people judge you by what you’ve yet to do, and you will judge yourself this way, too. Just do me this favor: Judge yourself less frequently, and with a little less disappointment, than everyone else does.

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People will say that they’ll put you on. They may or they may not. Don’t take it personally.

We entrepreneurs can’t help looking for that big break in our endeavors. A couple weeks after I went freelance, I met with an editor at my favorite publication who said “My dream for you is to be one of our contributing writers on our masthead.” In eight or nine years, I’ve followed up with that person in more ways than I can count and, while I still write for this publication from time time, my name is not on the masthead. This is not a sob story, like the rapper who loses a record deal. Or the singer whose first album gets shelved. Or the top model who wins a competition but doesn’t actually get a career from it. Big breaks don’t always happen when, where and with whom you think. Just when you think it’s only White people who string you along and make promises they can’t keep, a Black person will do it, too. Just when you think it’s only Black clients who support you and come through on their word, a White client jumps in with an alley-oop. Don’t let the disappointments (and there will be many) keep you from believing in the goodness and helpfulness of others. Which leads me to my next bit of advice.

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There are no guarantees.

My biggest disappointment in my career? A feature story that was killed due to some personnel shifts and a major redesign at a top women’s magazine. It was my first long-form narrative piece, a love story about a cancer widow. I was certain that it would be a defining moment in my career. It would show editors who only knew me for writing so-called “fluff” and service pieces that I could do serious journalism. It was my first time traveling on assignment, but I felt like an imposter, not a real-deal journalist. What I’m saying is there will be opportunities and promises of opportunities. Many of them will happen, some of them will not. Just remember that some is not all, and many is more than some.

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At some point, you may need to ask yourself, “Does following my dream require not having a job at all or just not having a job like the one I had?” And that’s OK.

Secure some kind of immediate income, supplemental or otherwise. Just because you quit your day job doesn’t mean that you don’t need a job. In other words, you may have to get another job. You had a 9-to-5, but maybe you can work a 5-to-9 and still follow your dream. And no, getting a job while you chase your dream is not a failure. Sometimes you have to quit your job to take the plunge, but you might have to get a job to stay afloat. I was a full-time magazine editor, which sometimes meant working long hours and came with restrictions about what other magazines I could write for. But when bills and rent were due, and the writing money wasn’t coming in, I took on freelance magazine work as a fact-checker where I could work a couple weeks out of the month and still pursue writing opportunities.

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Don’t believe the hype.  

Be careful when you pat yourself on the back and when other folks pat you on the back, too. People will congratulate you on your courageousness for making this big leap. When you have your first big success post-leap, people will say, “Go, girl! Look at you!” Enjoy it, receive it, say thank you. Just don’t let it go to your head.

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Finish one thing a day.

There’s a lot you want to do. But if you try to do too much, you might do nothing at all. Just do one thing at a time.

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Write down your dreams and big ideas. Review them once a week. This will keep you motivated.

For nearly a decade, one of my motivating dreams has been how awesome I’ll look wearing a colorful vintage kimono at my book release party. I want to look like Black girl cotton candy, but to do so, I have to write the book.

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When people ask you what your plan is, and you say, “I’m walking by faith,” don’t get defensive when they seem dubious.

You are not the first person to quit a job and follow their dream. Yes, you’re determined to prove the doubters wrong. But have the self-awareness and good sense to know that not everyone is as convinced of your inevitable success as you are. Don’t hold it against them.

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Keep your eyes on your own paper.

The comparison game is a bummer. I’d guess that entrepreneurs play it more than others. Essentially, we entrepreneurs are chasing a kind of stardom, to set ourselves above the rest, so we look to see who’s already shining brightly in our industry. This is a necessary practice. But it’s a dangerous one. Do it sparingly and deliberately. When you find that you’ve been down a comparison-based rabbit hole for more than 20 minutes, come up for air.

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Never be ashamed of where you are.

Don’t be ashamed of your success (wild or otherwise), your failure (epic or otherwise), or your in-between-ness. Life is long. Who knows if or when you’ll arrive, but the good news is that you’re on your way.

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