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Why Everybody At Least Needs A Side Gig

I recently listened to a very interesting radio interview with the drummer from Aerosmith, Joey Kramer. As I live outside Boston, it’s not unusual to hear Aerosmith band members on the radio when they pass through town since they’re from the area. What made this interview particularly interesting was the topic—gourmet coffee. Kramer was there to talk about Rockin’ and Roastin’, a business he launched in 2012. The interview started out covering the basics of the business—organic/eco-friendly grow methods, and the differences between the handful of coffees his company produces. Then the question of “why” came up. Why did Kramer start this business?

Was it because he needed money? Was it because he was bored? Nope. Aerosmith is one of the top-grossing rock bands in the history of the universe and they’ve been touring for more than four decades. He has plenty of money and too little free time to be bored.

Nor is it some sort of celebrity endorsement where he lends his name to the brand and merely shows up for advertising shoots and the occasional appearance. “When I have a business meeting with a potential client they always seem surprised when I walk in the room…like they expected to be meeting with a representative,” says Kramer, whose hands-on leadership of the company begins with bean selection and ends when a cup of his Guatemalan, Ethiopian, or Sumatran coffee hits his customers’ lips.

Then why would one of the most successful drummers from one of the most successful rock bands of all time start a side business? Aren’t Aerosmith’s monumental accomplishments enough? They’ve gutted their way through some very dark days and emerged victorious with over 150 million albums sold and too many awards to list. Why would someone with that track record start a side business from scratch and work so hard to make it profitable?

“Because I needed something of my own,” shared Kramer.

If you understand what he means, then you’ve already won half the battle. We all have an inherent desire to create something of our very own, to call our own shots and make all of the major decisions as we nurture that creation. You might already have a “good” job and no real reason to strike out on your own, but you still relate to Kramer. It’s a declaration of independence of sorts—a statement that your current job does not define you and the company doesn’t own you.

This is a very easy concept for unhappy employees to grasp. They sit at their desks all day and dream of being somewhere else doing something they want to do instead of what they have to do. And they long for the day when they can walk out of the office for the last time and never look back. But if you’re otherwise happy with your job you may feel no such pull toward starting something of your own and staking your claim. Why bother? The money’s pretty good, right? And you don’t have to worry about all those pesky details that come with being the boss instead of working for one. Or maybe you’re kept there by the “golden handcuffs” (i.e. good money for relatively little work/stress), have job security, and might as well ride it out where you are until retirement. That may sound nice but here’s the thing—you are probably going to be fired.

All business relationships—without exception—will end. The only question is will it end on your terms or someone else’s?

If the current economy teaches us anything, it’s that the chances of things ending on your terms are lower now than at any other time in history. Globalization and technological advances are extraordinary phenomena that can add great value to our lives, but they are also double-edged swords. The same technology that keeps us connected to friends and family can put entire industries out of business seemingly overnight. How many travel agents do you know? How about mom and pop hardware store owners? Even highly educated professionals like lawyers are feeling the squeeze from websites like that can accomplish virtually the same thing for a fraction of the price. These are just a few examples of market forces’ effects on jobs. What about the human factors?

As an adjunct educator, much of my income depends on how well I can get my foot in the door at a university and tee up teaching contracts. Over the years I’ve always been struck by the relative ease with which I’ve received contracts and assignments at the expense of other instructors who, in some cases, had been teaching those courses for years. And it’s happened to me a few times as well. That’s just life and business – everything is competitive. At least in those cases, you have the chance to get up to bat and take a swing. But there are other times when things go “poof” just because your boss who used to “take care of you” or the purchasing agent you spent years wooing moved on to greener pastures and was replaced by Genghis Kahn. Basically, Genghis has a new vision for the company and you aren’t in it. He has his own interests and people to take care of.

What then?

Young people seem to get this more than others. Too often we beat them up complaining that they are apathetic slugs that lack commitment and want everything handed to them. First, that describes a lot of older folks I know so I don’t think it’s unique to Millennials. Second, who can blame them? They grew up hearing the same things the rest of us heard from our parents and teachers—work hard, get good grades, go to college, get a job and be a loyal employee. Your employer will then take care of you, and after 30-40 years you will retire with a pension.


My grandfather worked as a machinist for General Motors for his entire adult life. When he retired he was rewarded with a cheap gold watch and a pension that barely covered his bad habits. And that’s the way it was supposed to be, steady work was respectable. My father got a degree in engineering and worked for GM for 10 years before he left to join a software startup. My grandmother jumped out of her knee-highs when he told her. “Nobody leaves GM! That’s a guaranteed job for life!” Years later, when my mother introduced my soon-to-be stepfather to her mother she asked him what he did for a living. He told her he was an orthopedic surgeon. “That’s nice, but are your working steady,” she asked. That was the mindset. Get a job and don’t rock the boat.

But as the Millennials grew older they didn’t see this play out very well. Instead, they saw their parents, grandparents, teachers, and neighbors buy into that narrative, put all of their eggs in one basket, and get royally screwed for their efforts. Can’t say I blame them for asking what’s in it for them before committing to anything. And this experience of getting unceremoniously canned overnight is not reserved for blue-collar jobs or positions that don’t require a ton of education and skills.

A few years ago I was sitting in a Boston pub with a buddy talking about the economy. I had just returned from six years of living in the Dominican Republic and my economic timing couldn’t have been worse.

“How bad do you think things will get before they start getting better?” I asked.

“The cream always rises to the top.”

He was implying that those who bring value will always be safe and he wasn’t being arrogant about it at all. But it was a bit naïve. When we spoke he was safely entrenched as a very high-level sales executive for a billion-dollar company—beautiful wife, two kids, McMansion in the suburbs and a Golden Retriever. About a year later he was recruited away by another huge firm and given his “dream job” (his words, not mine). His wife was able to immediately quit her job and all was well in the universe. Until about sixty days later when he was canned overnight with no explanation. Done. Gone. Out. Things were rough for him for a while but he eventually landed on his feet. Lesson learned—only tax collectors and funeral directors have job security.

Other people can see the writing on the wall and know the end is near, but they still don’t act until forced to do so. Then they panic and scramble to replace the job they hated with another job that probably won’t be much different. After all, they just got canned. How much bargaining power does that give them with the new job? Typically, not much. Left with few other options, they ride that wave until it also crashes on the beach. Rinse and repeat. In the process they are paying the bills and putting food on the table (always a good thing), but also selling themselves way too short.

Schlepping along at a job that we hate comes at a price. We put our dreams and aspirations on hold and never end up getting to them. Big mistake. We have a finite amount of time in our lives and the clock is always ticking. The least we can do is nurture a side project, especially while there is relatively little pressure to monetize it. If that’s not enough motivation, consider the research results of Bronnie Ware, an Australian nurse who spent a few years working with people in the final weeks of their lives.

“When questioned about any regrets they had or anything they would do differently,” she told The Guardian, “common scenes surfaced again and again.” Can you guess what the #1 regret of the dying was?

#1: I wish I’d had the courage to live a life true to myself, not the life others expected of me.

“This was the most common regret of all,” said Ware. When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realize, until they no longer have it.”

How many times have you heard the phrase “timing is everything?” But in most cases the only way to tell if your timing was good or bad is after the fact because too many things are completely out of our control to know in advance. So the phrase might as well be “it’s good to be lucky.” Here’s the truth when it comes to timing – the perfect time to start your project/business, write your book, fight for your cause, start a movement, or change habits is right now. You owe it to yourself to get started.

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