After eight years of higher education he landed a dream job, then left it all to be his own boss.
I was 26 when I graduated law school, and landed a job at one of the largest law firms in the country. My parents were proud, and I didn’t have to stress about the bar exam anymore. I felt accomplished and successful. Then I started working.
My job wasn’t anything sexy. I was drafting oil & gas title opinions for energy companies looking to drill for natural gas in Appalachia, frequently traveling to remote locations to conduct title searches at local courthouses.
Some of my friends thought, “Oh, you get to travel all the time. That’s so awesome. I don’t get to travel for work.”
My reaction was usually, “Dude… you get to go to Chicago… Pittsburgh. Have you ever spent a day in Wetzel County, West Virginia? Noble County, Ohio?”
Nothing against those places. They were beautiful actually. But I usually had to spend four hours a day in the car to commute, or stay at the cheapest remote hotels. (Big shout out to my regulars, the Super 8 in Saint Clairsville, OH & the Microtel in Washington, PA.)
I sometimes got to work out of an office. But when I did, there were several things that really rubbed me the wrong way. For one, I had to keep my mouth shut. Even when I offered advice, or asked questions, I was brushed aside or put in my place by a senior attorney.
Those who played that little game of brown-nosing and laughing at their (awful) jokes were routinely treated better. If you were politically correct, and talked crap behind people’s backs, it was worth it in the long run because only so many attorneys were made associate each year.
Secondly, people were getting fired every week. Nobody felt safe, because we were at the mercy of the client. If oil prices dropped, and their budget got reduced, we saw less work, and the firm trimmed the fat.
Luckily, I was an extremely hard worker, so I was seen as an asset. I was never worried about getting let go, but I romantically fantasied about it, like, “What if I just got fired today, wouldn’t that be amazing?”
And worst of all, I was bored. Luckily this was the type of job where I could have headphones in all day, so podcasts kept me company.
One day, toward the end of my time at the law firm (spoiler alert: I quit), I remember hearing Jeff Sanders from “5AM Miracle” say that humans weren’t meant to sit in a chair 10 hours a day. I knew he was right. My back hurt, I ate like shit, and I was depressed — mentally and physically.
“Entrepreneur on Fire,” which is still another one of my favorite podcasts, made me realize that I wasn’t the only person to ever feel this way. I heard story after story of entrepreneurs being in the exact same situation I was in, pivoting, working hard, then succeeding. I resonated with all of them, and I knew deep down I was meant for so much more.
Instead, I was still waking up every morning and apologizing to myself in the mirror for not maximizing my full potential in life.
It was toward the end of 2014 when I realized something was seriously wrong. My eyesight wasn’t perfect anymore, I was out of shape, and I was depressed. I had no clue where my career was going. I would yell at myself at random times, “What am I doing?” I constantly heard a voice in my head saying, “I have to quit my job, I have to quit.”
But was I really going to press the reset button after spending eight years in higher education and landing what most new attorneys would call a dream job? I had sold things online before, but I had never been a full-time entrepreneur.
Sure, I’m a huge risk taker, and I’m really good at networking. But how am I going to make money for myself? Could I really be a success story like all the entrepreneurs I heard on “Entrepreneur on Fire?”
When my girlfriend and I contemplated the pros and cons of quitting my job, here are the bullet-points we struggled with, with a pro & con for each. (Keep in mind, my girlfriend teaches first grade, so she was done in June, and she was looking to change schools anyway.)
Quit so we can move wherever we want.
Pro: Mobility, happiness, more time together.
Con: Moving is expensive, and we would likely move to a bigger city, so higher cost of living.
Quit so we will be happier.
Pro: We wouldn’t argue over stupid things. Our depression over bad work-life balance triggered arguments over nothing. We were both stressed, and it affected our relationship outside of work. And another pro, we would spend way more time with family.
Con: We might have new problems- financial, smaller living space, etc.
Quit because there’s something better out there.
Pro: Flexibility to do whatever I want. I knew that if I just had a little time off to figure things out, I could start a business and replace my paycheck within a year or so.
Con: I had no idea what I wanted to do. I was doing a bit of real estate investing, so I thought I could make a podcast about it. But beyond that, I figured my networking skills and hard work ethic would take me where I needed to go.
Quit because we’ll be healthier.
No pro & con list needed here. I was absolutely sick at work. By quitting, we could get into a better sleep cycle, keep a clean home, eat healthier, and get back into working out consistently.
Stay at my job because we need money.
MONEY. No matter how compelling the previous four arguments were, money was the kicker.
Understanding the Value & Valuing the Understanding
Money always rules as the most important factor in these situations. Why? Well, here’s my professional opinion — it’s hard to quantify things like having to give 30 days’ notice for time off, working with an amazing boss, or a 10-minute commute. Sure, they’re factors, but you can’t really put a numerical dollar value on them.
Really think about it. Now make these decisions in 5 seconds.
Would you take a $5,000 pay cut RIGHT NOW to have an incredibly cool, understanding boss?
Would you take a $10,000 pay cut RIGHT NOW if you could work five minutes from home?
Would you accept a $10,000 raise RIGHT NOW to work with a superior that harasses you?
What about if you had to stay at work until 7:00 PM every Friday?
See how hard this is?
The fact of the matter is most people rank a job’s quality in terms of salary — a number. Oh, $30,000, that’s a bad job. Wow, $140,000, that’s a great job.
Americans, especially those young ones coming straight out of school, are so primed to look at that number and rank it as “better” like that’s the only factor that matters! They don’t see the intangible forces that devalue quality of life, and the collateral side-effects that result.
You want to pull in a six-figure paycheck? Stuff your fat face with Chipotle, then go back to work at 8:00 PM on a Thursday while your friends are out grabbing cocktails. Get used to apologizing to your parents, because your other siblings will make time for them, and you won’t.
These are the sacrifices you make when you surrender to a number.
On February 6, 2015 I quit my job.
Since then, I have jumped into a sea of like-minded entrepreneurs who want the same thing I want — to create something for themselves. I have leveraged my people skills into actual business relationships. I have amped up my real estate investing, grown a successful podcast, learned social media enough to start charging consulting fees, done legal work on the side, and currently I’m working on launching my first online course. I’ve even landed coaching clients and a speaking gig.
During my TEDx-style talk at Podcast Movement, I said, “The corporate world robbed me of my time, but worst of all, it robbed me of my voice.”
Well, I have a say in everything now. As an entrepreneur, I don’t ever have to live by someone else’s rules, kill my physical health to crank out a paycheck, or sacrifice my core values to adhere to some American model of success.
What is success anyway? Success can only be defined by you. Not your friends, your parents, or your spouse. Everybody has their very own personal idea of what success means to them.
My best advice to someone struggling with the decision to quit their job is to know yourself. If you understand what success means to you, then it’s easier to chase.
So, sit down with your family and take a broad perspective look at your life. Write down the good and bad results that your career change might have on each aspect. Focus on your mobility, flexibility, happiness, health and money. If you can get over the money aspect, you’ll value the other four variables of the formula a lot higher.
I understand leaving a good job is a lot harder than leaving a bad one. But the opportunity-cost is extremely high for not doing what you love for the rest of your life. Assess yourself, your current situation, and your values, and you should come to the answer you’re looking for.