4 Lessons In Entrepreneurship I Learned From Working So-Called Dead-End Jobs

Starting off doing grunt work could be just the motivation you need for a startup-worthy work ethic.

4 Lessons In Entrepreneurship I Learned From Working So-Called Dead-End Jobs
[Image: Flickr user Evan Blaser]

My journey in entrepreneurship began over a decade ago when I was 15 years old microwaving gas station food and scrubbing diesel off of the concrete slabs beneath the avocado green fuel pumps.


Over the years I took on roles as a dishwasher, a pizza delivery driver, a salesmen, a shoe stocker, a clothes folder, a cold caller, a boat cleaner, a landscaper, and a house painter. Each of these jobs taught me something valuable, but as I get older I realize just how much they’ve played a role in my path to becoming an entrepreneur.

Here are four things I took away from my years in these everyday jobs that groomed me for entrepreneurship:

1. Perspective

As an entrepreneur, things are likely going to be rough. Perspective is needed to slog through the hard times.

Someone who has a history of working overtime, saving money, and not getting paid benefits or sick days can generally appreciate the little things. Their pain points feel less significant because they’ve already been through numerous pain points..

As Chris DeVore, founder of venture capitalists Founders Co-Op, says: “Nothing helps you appreciate both the good days and bad as an entrepreneur than having been a cog in someone else’s machine.”

2. Empathy

The Shell Station I worked at was near an oil refinery, and so our customers were primarily tradesmen. Hands always stained a charred black, I thought they were loud and crass and different from what I was used to. Then one day, everything changed.


There wasn’t a magical moment; I just developed an appreciation for them. They paid more attention to me than the customers I would have expected to identify with and always had something to say. These were the customers I looked forward to seeing most.

Empathy is the ability to walk in someone else’s shoes and to comprehend their struggles as if they were your own. Work at the proverbial gas station and you’ll be able to empathize with the best of them.

“You have the opportunity to develop relationships with people you are unlikely to meet in the startup world and to appreciate their struggles in a way that going straight from college to startup jobs cannot show you,” said Rand Fishkin, co-founder of inbound marketing software company Moz.

3. Customer Service

People can be weird. The only way to get past this is to expose yourself to the weirdness.

Delivering pizzas or cold calling people will prepare you for working with customers at a startup better than any customer development course. For a while you’ll feel like you’ll never appreciate those whom you don’t understand. And then one day, on your 600th delivery to a person who always answers the door naked with a cigarette stuck to his lip, things will just click.

It’s not science and it’s not something that can be taught. It just takes time.


4. Drive

Drive fueled by perspective is a force and can push you to work harder then you ever thought possible.

Marc Nager, CEO and cofounder of entrepreneurial community nonprofit UP Global, says the foundations for work ethic and drive are set early on.

“In my experience, people who have excelled in fast-pace, customer service roles have a set of values that help them excel in their careers later in life,” he says. “Jobs that require you to work long hours, have you striving to be more efficient, and force you to keep customers smiling no matter what set the tracks for great characters of leadership, communication, and hustle.”

You’re likely too late in life to go back to a place where working at the proverbial gas station makes sense. So what are you supposed to walk away with here?

Perspective, I hope. The world is a rough and tumble place, even in the context of the first-world-problems we’re discussing here, and it’s important that we all take proactive steps back in order to see clearly what’s ahead.

Chet Kittleson is the Director of Strategic Partnerships at UP Global.