When my family relocated to Florida a number of years ago, it was in part because my husband loved fishing and thought he wanted to make a living working on the water. Soon he was testing the adage, “Do what you love and the money will follow.” He secured his captain’s license, set up a fishing charter business and soon learned that the business of fishing was quite different from the sport of fishing. Needless to say, when he fishes now, it’s for pleasure, not work.
One of the biggest shocks for entrepreneurs is that when they start a business to do what they love, they often find out they don’t get to do what they love as much as they’d like.
“I didn’t realize how many different disciplines I’d have to learn quickly and competently,” says J. Colin Petersen, President and CEO of J – I.T. Outsource. “I had to become a marketer, PR guy, recruiter, bookkeeper, janitor, tech, counselor, coach, sales guru, logistics manager, purchasing and fulfillment expert, the list goes on.”
Kyle Taylor, founder of The Penny Hoarder, got into blogging because he liked the “science and analytics behind blogging.” But massive success forced him to confront the truth about running a business: “The one thing you really love doing may not be what you get to work on all day,” he warns. “You’ll find yourself in all kinds of meetings from PR to advertising to tech. You have to be prepared to wear multiple hats at all times.”
In addition to the role of CEO, many entrepreneurs often find they must also fill the roles of:
• CFO: learning how to manage cash flow, ensure employees get paid on time, researching small business loans and financing options, securing funding
• CMO: marketing, selling, advertising and public relations
• Human Resources Executive: hiring, firing and managing employees, researching and choosing benefits
If you are thinking of starting a business, you’ll want to keep in mind that those roles will have to be filled, whether by you or someone else.
Where’s the Glamour?
“What has surprised me – and what I still struggle with – is seeing the reality of being an entrepreneur beyond what’s in the media,” says Dimitri Zakharov, CEO of Impact Enterprises, a social outsourcing company that provides digital jobs for skilled youth in Africa. He’s helped build the company to 60 full-time employees in Zambia.
“With a lean team, everyone has to be a jack-of-all-trades, which means taking on responsibilities way beyond your usual capacities,” he says. “Most companies don’t have thousands of customers and are struggling to grow at all. It’s really very mundane, stressful work with little guarantee of success. But the idea that you can build something meaningful keeps you going.”
It’s also easy to forget, when starting a business, that ultimately someone has to sell what you have to offer, and at least in the initial stages, that someone may be you.
“I thought, when I was starting my own business, that my job was going to have a lot more exciting new roles I would be filing,” explains Mark Tuchscherer, co-founder and president of GeeksChicago.com. “My job is a lot of sales and trying to generate new leads. I love not having a boss, but I never thought I would become such a sales guy.”
Expect to Get Your Hands Dirty
“I discovered that in order to be a successful entrepreneur, I had to be willing to get my hands dirty,” says Ross Cohen, co-founder of BeenVerified.com. “That means picking up the phones and talking to customers, learning to code, or even taking out the trash.”
“As a co-founder of a startup, there is no single job that is ever above or beneath you,” he said. “For a long time, my job on a day-to-day basis was really just whatever resources we were lacking on that day. I’ve done everything from designing our website in Photoshop to coding our conversion funnels in html/css. Some days I was the sales force and others I was the customer support team.”
Yet despite these challenges, or perhaps because of them, entrepreneurs learn how to adapt and grow.
“One positive part of being an entrepreneur is you do get a lot more flexibility, but if something goes wrong or you need to step in and help with issues your work day can be a lot longer,” says Tuchscherer. “The buck always stops with you and you need to be the main person around when needed for problems. This can make your schedule a little chaotic and unreliable.”
For some, taking on multiple roles can even be energizing. “Going into entrepreneurship, I knew I would learn and grow a lot, but I didn’t realize it would happen this fast,” says content marketer Edward Sturm. “I love it. Everyday I’m becoming more knowledgeable and qualified than my peers stuck in an office.”
“The amount that I’ve learned, both about my craft and about myself, over the past year has been nothing short of staggering,” Sturm adds. “From a business perspective, I’m doing things I didn’t know I could do, and from an emotional perspective, there’s very little that makes me feel anxious and my level of equanimity in all situations has skyrocketed.”
This article was originally written on June 1, 2016 and updated on February 1, 2021.