The Joys And Perils Of Being Your Own Boss

What no one tells you about freelancing and entrepreneurship.

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| February 02 2017,

7:00 pm

June 2017 will mark my second year of stepping-out-on-faith-aversary. I totally made that holiday up, but it’s pretty unique to me. For almost four years, I worked as a morning news producer and on-air contributor for a top 25 news market. At age 23, I walked in the door as a rookie news producer and through many trying days, I finally rose through the ranks becoming a senior news producer. I met several A-listers, covered big stories for the city and showcased my personality every morning in a short segment. The highlight of my career was gaining access to see President Obama during his visit in Uptown. 

With all the perks, something was missing. I didn't feel fulfilled. On the surface, I appeared as a 20-something making good money and attending exclusive events. My Facebook friends and college classmates marveled at seeing me on TV. Meanwhile, I was sleep deprived after working overnight hours and 12-hour shifts without a lunch break. Could it be, I was burned out? 

Yes. Burnout is real.

Exclusive image of me every day when my alarm clock went off for work.

Photo: Popkey

I prayed. And prayed. Then cried. And prayed some more. My quarter-life crisis was settling in and I didn't like the person I was becoming. I went to Bible study, prayed with friends and put in extra tithes every Sunday. The only thing missing was the anointing oil, which I was close to purchasing off somebody's church website.

As I watched my friends advance in their careers, pursue higher degrees and start their families, I felt like life was passing me by. You see, I didn't become complacent. I actually put my faith into action. I applied and applied for similar news jobs, but nothing seemed to hook. Little did I know, the universe was shifting my interests and preparing me for a leap of faith. 

Eventually, I made peace with my current job situation and searched within to decide my next move. I prayed my last prayer. One morning, while I was preparing for my segment, I went inside the women's dressing room, looked in the mirror and said, “God, this is my last time coming to you about this. Should I stay or should I go?” After months of thinking, God had stopped listening to me. He finally gave me the confirmation. Thirty minutes later, I wrote my resignation letter and haven’t looked back. 

A few days before my last day on the job, I went to Bible Study and was introduced to a lady who had recently quit her job as a news anchor to start a production company. I asked her, “Forgive me for being nosey, but if you quit your job, how do you get money?”. When I put this forward question out into the atmosphere, I was expecting her to give me a “mind your own business or how dare you?" type response. She didn’t. Instead, she replied with the best advice ever. This stranger, who would soon become a close friend of mine said, “Tyler, when you need money and your bills are due, you’ll figure it out.” 


Archive image of how I looked at her.

Photo: Pinterest

Seriously, what was I supposed to do with that? Life is all about figuring it out, I get it. We’re all on a pursuit of knowledge, but come on now, I thought she was just being greedy. Little did I know, this simple guidance would be the bread and butter for the next two years of my life. 

I had my last day at the station, said my goodbyes, took a deep breath and went on to a different world (just like Whitley said in the series finale). My mind was so focused on not having to be at work at 1 a.m. on the following Monday, I couldn’t see anything else. I was confident that I would soon become this big-time Hollywood TV writer, therefore nothing else matters.

How I picture God laughing at my arrogance.

Photo: Jasira Monique

As I spent my time at home writing scripts and building my future, I didn’t see my part-time job fizzling out. I didn’t see the website I contributed for shutting down. I didn’t see friendships ending. I didn’t see what was ahead for the life as an entrepreneur. No one can quite prepare you for this lifestyle. Don't let Robert Frost fool you, there is no GPS for the road less traveled.

You can read as many books as you please, attend workshops, network for your life and freelance to make ends meet, but it's all about the situation you create for yourself. The price tag of entrepreneurship and passion comes with a cost. Late nights, extremely early mornings. No one understanding your vision. People wanting your best and only wanting to compensate you for less than your value. Broken promises. It can all be a lonely place. You’ll wake up with excitement and ride the wave of emotions varying from frustration, confidence, disdain and humor. You have to be mentally tough to get anything done for yourself these days.

 Here are a few things I’ve picked up along the way. As cliche as it sounds, there is a cost to being your own boss.

Photo: Tumblr

What I failed to tell you about my leap of faith, quitting my job, was that I saved loads of money. As a freelancer and entrepreneur, you will need money for rainy days because it rains a lot in our world. It is wise to at least keep one year's worth of rent on deck and then some. Consider getting a roommate. If you need to move back home, put aside your shame and go back home if that is an option. Cut down on necessary expenses. 

Do you really need a fire stick, cable, Hulu, and Netflix?

Photo: Tumblr

When I watched The New Edition Story last week on BET, the most poignant quote came from Tank’s character who played the boys’ shystie record executive. He looked Michael Bivens’ character (Bryshere Gray) straight in the eye, with little emotion and said, "People are going to say a lot of things in this business, but the only thing that matters is what's on that paper in front of you." 

Photo: Tumblr

That’s for every industry, even yours. Don’t put your name on anything unless you’ve had someone like a lawyer or someone with legal expertise review the document. Do get everything in writing. You are one signature away from becoming an Unsung episode if you blindly enter into deals without caution. Subscribe to newsletters and blogs with expertise about the industry you're pursuing. We're in the age of innovators and great thinkers. It's 2017, there's really no excuse for you to say that you don't know how to do something.

Find your tribe. Not just anyone, surround yourself with good people. I’ve been fortunate enough to encounter individuals with a genuine interest in my growth. They refer me to jobs all the time and vice versa. We look out for each other. If you can be the plug for someone else, do it with no expectation of getting something else in return.

Hell hath no fury than the tax man. Save your receipts. Familiarize yourself with tax codes and write-offs. Get organized and don't wait until the last minute to keep track of your finances. Invest in an accountant or find a friend who is good with numbers. 

Don’t be afraid to ask for help! When you’re steadily grinding and building for yourself, it feels like you’re out on an island alone. You cannot do it all by yourself. Ditch the idea of “Beyonce has 24 hours in a day, what’s your excuse?”. You know those dumb memes floating on Instagram and Facebook. Mrs. Carter has a team of 50+ people that help her walk to the car. Don’t play yourself. Find college students wanting to intern and gain experience or consult other business-minded individuals willing to barter services to help you in the areas that you lack expertise. 

Find the money. Millions of ideas go to waste every year (there are no actual figures on this, I made it up) because people are crippled by the thought of securing funding. Learn how to write grants. Solidify your pitch before seeking out solid investors. Don't rule out crowdfunding. A man once earned $55,000 from online backers to make potato salad via Kickstarter. Your dreams are valid.

Always remember, someone had to help you at some point or another in your career. Don’t be stingy with knowledge. A key business component to entrepreneurship is relationship building.  Take a genuine interest in seeing others around you win. Send thank you notes and "thinking of you" emails. Don't just contact people when you need help. You never know when and how you will need someone. Sure you’re bombarded with emails all day with leeches asking for something for free. You’ve worked hard to get to where you are and no one expects you to give your expertise away for free. But do, pay it forward. The email that you’re ignoring could very well be the next Barack or Beyonce wanting to put you on the team.

And finally, you must be willing to become a student of your craft. Starting off, you will be your own intern, accounts receivable, accountant, digital strategist, and publicist. The beginning is never easy, but the payoff is always greater than you can imagine. In the last two years, I haven't had one hungry day, all of my bills were paid on time (somehow) and I've unlocked new opportunities every day. I'm not a TV writer yet, but I do have a serenity by taking control of my career. You can't put a price tag on peace of mind.

Photo: Tenor

milennial entreprenuer
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