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Side Hustling Tips

How to Be Successful in Your Life: From Freelance to Fortune 200

What is Success?

 

“What are your career goals?” My manager asked, a look of genuine concern on her face.

“I want to do what I’m doing here, from anywhere,” I said. “I want to be with my family at home, and I want a career. I want to be happy.”

“What you want to do can be done. But, I want you to know it’s extremely difficult.”

“I know,” I replied.

“I just want to make sure you fully grasp the great opportunity you have here,” she said, that same look of concern on her face.

I knew what a great opportunity I had: the chance to redo the voice of a Fortune 200 brand. And, I was about to get up and walk away from it all.

 

The Concept of Success

 

When I was a kid, I wanted to be an archaeologist, like the great Howard Carter, who discovered King Tut’s tomb. I knew if I accomplished that as an adult, I was officially successful.

Fortunately, I matured a bit as time went on. In the sixth grade I saw “What Women Want” in theaters and said to myself, “If I have a job like Mel Gibson’s, writing the slogans for brands, I will be successful.”

Success has a funny way of shifting on us, transforming as we age and discover different passions and talents. While I’m unable to read women’s minds and I don’t write ad slogans for brands like Nike, I do write copy for brands and help them define their identity with great copy. I’d say that’s pretty close to Mel Gibson’s character in “What Women Want.” So, am I successful?

 

College: Redefining Success Three Times in One Year

 

My dad worked a lot when I was a kid. It’s something I will always be grateful for, as he helped put a roof over our heads, and he taught me the value of hard work. For him, success in life meant working hard and providing for his family, no matter what.

When I went off to college, I pinballed around, bouncing from one major to the next my first year. I knew I wanted to do something that would make my family proud, and I knew I wanted to be successful. But what did success look like? I knew to my family, success meant working hard and working a lot.

I could get my business degree and go the traditional route. Or, I could study marketing and get into the professional world that way. After much internal debate I did what anyone in my shoes would do: major in English with a focus in creative writing.

“Are you going to teach?” My family and everyone else asked, hope in their eyes.

“No,” I began, “I’m going to be a writer.”

And the room goes mild.

“Enjoy working at Starbucks for the rest of your life,” became both the most-said greeting from my friends and served as a constant reminder that I better not mess this up.

 

Post-College, or “Oh shit, what have I done?”

 

A few months after graduating with my English degree, I was in the most likely of places: Best Buy. I had been there for most of college and found myself the lead of security and safety. A noble position, but not what I had in mind when I set off from high school. Still, it kind of paid the bills and I was getting decent leadership experience that would surely carry over into something. Maybe?

Only a few months into my lead spot, the company restructured and I had to step down, passing the torch to someone with more experience so they could lead that department and more. I didn’t mind, and the pride and joy this newfound position brought my coworker gave me happiness and envy. At their young, barely post-college age, they had found success with a retail company they planned on staying with for life.

I was back at square one, with a smidgen of leadership experience under my belt and no professional writing experience. Then it happened.

 

Freelance: The Gateway to Professional Writing

 

It had been several months since my graduation when an acquaintance asked if I’d like to take on a freelance client. She was too busy and I was desperate for experience. A day after I gave her an eager “Yes” I had an email in my inbox asking for a description of my experience and an inquiry about my usual rate.

“Usual rate?” I thought. “College credit? Pity?”

I called my friend, who told me to, “Tell them something reasonable, John. Say $15 an hour, and settle for $13 if they can’t do that.”

My jaw dropped. Fifteen an hour? I was making several dollars less than that at my full-time job. I was rich!

Was this what success felt like? Had I finally made it?

For a moment, yes!

I wrote article after article, week after week. The money was steady and the experience was incredible. I had no idea what the hell I was doing, but by God I was doing it! I was a real, paid writer!

 

Redefining Success, Again

 

A little more than a year after starting my freelance position, the emails stopped coming. And with the email shortage, the work stopped coming, too. That was it. Game over, man.

But there was hope. A job posting for a sales job at a local publishing company. I hated sales, but my then girlfriend had the great idea of applying for the job, but making everything on my resume about writing. It was a risky gambit, but I wasn’t about to let success slip through my fingertips. So, I applied for the sales job, making sure to mention only my writing background and none of my sales experience.

It worked.

A few weeks later I was starting my new job as a copywriter for a publishing house. If I was officially a writer with my freelance gig, then I was REALLY official now. Success, meet eager writer.

 

A Mundane Success

 

Fast forward one year. I was still a copywriter, pumping out 20 press releases every week with no end in sight. There was nowhere to go, I’d reached the top of my department. My skills felt like they’d plateaued and I was simply earning a paycheck and making my years of experience a larger number on my resume. (I’d appreciate the importance of this later.)

Was this really success? Working all day simply to work?

Like a bad late night TV ad I thought to myself, “There has to be a better way!”

 

A Promotion in Success

 

A few months shy of two years into my stint as a copywriter and I found my out: an opening for an email marketer in corporate marketing at the same company. Bingo.

A few good words put in with management by a coworker, some mocked up samples of emails I’d never before created, and a great inteview later, and I was officially an email marketer in the corporate marketing department. I’d reached the top!

Well, the top at that moment.

See, a funny thing happens when you get something new – it eventually gets old.

 

Moving Southwest, Moving Up

 

One-and-a-half years into my time as an email marketer, my wife and I moved across the country, got married, and had a baby. It was a busy year, to say the least. My company was nice enough to approve me for remote, something they never do, so I was able to take the job with me to Texas.

During that time I also found myself in the new massive job market of Austin, applied for countless positions, and found a whole bunch of disappointment.

Then our little guy arrived and suddenly I found a whole new motivation to kick some major ass. One billion job applications later and I found a better-paying job with a startup, and left my email marketing job.

 

Sacrifice Does Not Equal Success

 

A few months into my job at the startup I realized something: remote life was awesome. Granted, I realized this after giving it up and moving into an office. The new job was really great and I was getting some great experience, but along the way I’d exchanged that huge chunk of freedom remote grants for more money and more stress.

What once felt like success, was now feeling like something else: regret. But why? I never felt this way with my previous jobs?

Having a kid really does change everything. Don’t let anyone tell you otherwise.

My definition of success was changing before my eyes, turning into something else entirely. What was once, “Climb the ladder and become a badass writer,” was changing. But what was it changing into?

 

Deja Oops: Going Back to Go Forward

 

Several months into my job at the startup I realized I needed some stability in my life. I trusted my instinct, and for the first time in my life, I walked away from a great writing position to go back to old faithful: my email marketing job with the publishing house.

I was working from home again, and appreciating that part a ton. But, there was the work. It was the same as it was before, and  I once again felt like my resume was stagnating. Even worse, I felt like my skillset was stagnant. A few months prior, at the startup, my boss had asked me for a piece of writing advice to inspire the team. I told her, “Never get comfortable. The worst thing writers can do is let themselves get comfortable. Comfortability kills creativity.” She loved it.

“Never get comfortable. The worst thing writers can do is let themselves get comfortable. Comfortability kills creativity.”

Now, I was going against that. I was comfortable, sure, but I wasn’t doing my own skills any favors. And, I no longer felt any semblance of success in my life. I had to get back to that. First, I had to figure out what success meant to me.

 

The Big Kahuna: Fortune 200 Success

 

After ten months of creating emails, I was ready for a big change of pace. I filled my creative urges with the occasional freelance project, but even that only does so much. To put it simply, I needed a new career.

I needed to find the success, again.

As if the employment gods heard my pleas, I found what looked like the key to success in a very large way: a job redoing all of the copy and branding for a fortune 200 company. This was the biggest of big breaks any writer could ask for. Especially one with only five years of experience.

I would be able to provide for my family, just like my dad did, and I would have the portfolio opportunity of a lifetime. What more could I ask for?

 

Three-Step Success Program: Quit, Panic, Enjoy Life

 

I started my job at the Fortune 200 company as a contractor. It was a three-month period where either party could terminate the relationship, no questions asked. The perfect way to test out being in an office again. A very corporate office, at that.

The first few weeks were great. The people were wonderful and the work was fun enough. I was getting to pitch some new ideas, a rarity in a company that big. But still, something didn’t quite feel right.

Then, one morning while I was at my desk it hit me: I wasn’t happy. I was driving an hour to work, working at my desk, driving an hour home, spending two hours with my family, and going to bed to start it all over again. I was working for the weekend more than ever before.

My dad worked a lot when I was a kid, and I appreciated that. But, something he’d said to me a year earlier stuck with me. “John, I wish I was around more when you were little.”

Me too, Dad. Me too.

That morning at my desk, staring at the grey walls of my cubicle, I finally understood the weight of my dad’s words. I was already missing my son, and no paycheck or big opportunity was going to change that. In that moment, I realized what success meant to me: being home, being happy, and doing what I love — writing.

As much as I didn’t want to accept it, I knew in that moment I would have to leave that job.

 

Defining Your Success: A Job for You

 

Leaving my last job was both the easiest and hardest decision of my professional career. That final drive home lasted forever, and numerous times I contemplated turning around.

Finally, I was home.

My wife’s smiling face greeted me, along with the untamed and wild yell of my son. I dropped down to one knee, bracing myself for the surprisingly powerful collision his little body elicited everytime he slammed into me and hugged my head. In that moment, I knew I’d done the right thing.

The next time you wonder how to be successful in your life, remember the most important thing: it’s your life. Nobody can give you the definition to success except you. Is creative fulfillment your goal? Do you want to climb the corporate ladder? Run your own business? Ask yourself what being successful in life means to you and forget about everyone else’s definition.

I’d never find success in a small cubicle, a hip startup office, or a corporate palace. I’d only find it with my family, where I was able to do the one thing I didn’t know I wanted to all along: be a dad.

Now, I’m working full-time for a great marketing agency, pumping out content marketing for numerous brands, and writing emails — all from home. And like the words of my dad, the price of success and my final conversation with my last boss will always be there to remind me of how I can be successful in my life.

 

“I just want to make sure you fully grasp the great opportunity you have here.”

“I know,” I began. “This is a truly great opportunity. But, it’s not my great opportunity, it’s someone else’s.”

 

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