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TD Magazine Article

Establish Your Side Hustle

Diversify your skill set and revenue stream by taking an entrepreneurial leap.


Wed May 01 2019

Establish Your Side Hustle

Talent development professionals understand better than most that the world of work is rapidly changing. In addition to the headlines about soon-to-be-extinct professions like truck drivers or cashiers, it turns out that white-collar jobs may be evolving nearly as fast.

In fact, a McKinsey Global Institute study states that "as many as 45 percent of the activities individuals are paid to perform can be automated by adapting currently demonstrated technologies," including senior executives' duties. The question, then, is how to ensure that we personally can stay ahead of the curve.


For the past decade, I've studied the future of work closely, and in my latest book, Entrepreneurial You, I lay out a strategy by which people can build true career insurance for themselves: developing entrepreneurial side ventures—even if you love your day job and have no intention of making a change.

Why you need a side hustle

Common wisdom tells us that people should diversify their investment portfolios because it's foolish to put all their money in one stock. But we're far less careful on the other end. Too many people rely on one employer for their entire paycheck or to be the sole source of their professional development.

The old model, the one that most of us grew up hearing about—"work hard, get a good job, and you'll be rewarded"—has changed. Hard work is still mandatory, but today the work has shifted toward an ever-more independent, work-from-wherever-you-are business economy. The very idea of what constitutes a career has transformed.

Whether you work for yourself or for others, you'll need to find ways to diversify your income streams, your network, and your learning. In most cases, your side venture may increase your status and marketability at work because of the new skills you're learning. And that's the best hedge possible against uncertainty—not to mention a way to increase your impact and earn more.

The benefits

Lenny Achan began his career as a nurse and worked his way up to becoming an administrator at Mount Sinai Hospital in New York City. But his career really took off when his supervisor discovered Achan had developed an app on the side. Achan was worried when he got called into his supervisor's office: Had he violated a policy he hadn't known about? Did they suspect he had been moonlighting on company time? As it turned out, his supervisor admired his initiative and promoted him to run social media—and eventually all communications—for the hospital.


Similarly, Bozi Dar has a traditionally successful career as a senior marketing executive for a Fortune 500 life sciences company. But he became fascinated by the possibilities of entrepreneurship, and in 2013, he also tried to build an app. It never earned a profit, yet he learned invaluable lessons in the process about marketing, sales, and business strategy. The following year, he tried a different tack: an online course about how to get promoted at your company, which has brought him an income of more than six figures.

However, Dar has seen some of the biggest returns in his day job, where he says his ability to bring a background in "technology and digital is highly desirable. It enabled me to completely reinvent myself." He considers himself an "intrapreneur," innovating inside his company, and he feels that continuing to operate in a large corporate environment, with its teams and budgetary resources, enables him to tackle "high-profile ideas that would be incredibly hard to work on as an entrepreneur."

It may seem counterintuitive, but spending time working for yourself, on your own side projects, makes you far more valuable in your full-time job. It also gives you more options in case your professional situation changes—as I experienced years ago, when I got laid off from my first job as a newspaper reporter.

Today, I earn my living in nine different ways: writing books, speaking, teaching business school, consulting, executive coaching, teaching online courses, facilitating in-person workshops, running mastermind groups, and making affiliate income (commissions when I refer people to purchase products or services that I endorse). If one of those avenues goes away, I have enough diversification that I don't have to worry—which is a reassuring position in today's uncertain economy.

Getting started

At this point, you may be intrigued by the concept of a side hustle, but where should you start?


Determine what product or service to offer. For some professionals, it's obvious what skills or knowledge they would want to share in an entrepreneurial venture. But for others, it can be a bit murkier. You may have a variety of interests or perhaps you're a generalist. How do you know what to focus on?

Dar recommends determining what people want rather than moving forward with an idea you think is cool. Dar's first product was an app that helped people change their mood by looking at their personal photos paired with music. He's convinced the reason it failed is that "I started my app not really testing whether there is a problem \[that customers wanted solved\], not testing what is my audience, not testing whether anyone was even searching for a solution. I just fell in love with my idea, started putting money and time into it, and it never worked." Don't just come up with a clever notion; first make sure people in fact want it.

Of course, it's essential to make sure that your side hustle doesn't conflict with company policies—for instance, your employer won't want you poaching its customers, so you will need to be careful if your side work is similar to your full-time work.

Understand what you're uniquely qualified to share. Dar's successful online career course arose from the questions others kept asking him. "I was getting promotion after promotion," he recalls. His friends and colleagues noticed, and "I found myself being invited for these coffee/mentoring sessions nonstop." He realized that others found his perspective valuable, and perhaps an audience may pay for it. In your case, you may have friends who are constantly asking you to edit their resumes, help them organize their closets, or give them photography tutorials.

Build your skills. Many people who are employed by companies, even if they're quite talented, may not be fully ready for an entrepreneurial venture at first. Prior to starting my business, I took professional development courses on topics I knew I needed to learn, such as financial management, design, and business strategy. Dar recommends that you take time to learn foundational skills, such as sales, oral presentation, persuasion, and copywriting. "Buying courses, joining a mastermind, and having a business coach will all help," he notes.

Build your audience. Your side gig obviously won't work well if you don't have customers. There are two key ways to build an audience receptive to your work. The first is networking, which enables you to build connections one-on-one or in small groups and interact directly with like-minded people. The second method is content creation, which enables you to make connections at scale, because more people can read an article that you've written or listen to a podcast you've recorded than you can ever hope to have coffee with. Working assiduously on both will enable you to share your ideas more widely and create an interested group that's ready to receive your best ideas.

Build your credibility. While it would be nice if people took the time to evaluate every single person on their merits in an in-depth fashion, that just doesn't happen. Instead, you'll need to make it easier for others to recognize your talents by accruing meaningful affiliations that enable people to say, "I guess she's worth listening to." Examples include writing for high-profile publications, being an officer of a professional association, and having well-known clients. Being thoughtful about this step enables a much faster ascent.

Remain focused. Although it may be tempting to try 10 different strategies at once, it's important to focus. When you're ready to launch, you can easily get overwhelmed with all the things you could be doing. Instead, Dar suggests mastering one channel at a time so you get really good at it, and you can build from there. In his case, he has one course, markets it via one channel (webinars), and identifies those webinar opportunities through one mechanism (referrals from partners). It's better to excel in one area and then bridge from there.

Land your first client. The real test of an entrepreneurial side gig isn't how good your idea is; it's whether anyone will pay for it.

When Michael Parrish DuDell, author of a book based on the Shark Tank TV series, launched his consultancy, he set himself a tough goal: If he couldn't close at least one client in 30 days, he'd shut down the business. He wanted to go all in during that one-month period and see if he could do it. "There's no do-overs, no retries," he recalls.

DuDell knew he thrived under pressure, and he kept focused. "I woke up every day with a single thought: 'You have to close, you have to close.' By the end of the first month, I had closed three big clients. I remember when I closed my first deal ... I had to be cool on the phone, because you have to sort of be professional, but the second I got off the phone, I just sat there \[thinking\], 'You just closed a $25,000 deal.'"

Of course, those deals didn't materialize out of nowhere. DuDell had to relentlessly seek them out, and that meant doing something that many nascent entrepreneurs find terrifying: asking for the sale. "I reached out to my network and told them what I was doing," he explains. "I think this is a problem, that people feel uncomfortable just stating what they're doing." When you first get started, you may still be unsure of your skills or focus area, and you don't want to risk embarrassing yourself in front of friends and colleagues. But asking for the sale is the only way to get business initially.

In the early days of your side gig, it's perfectly OK to start small: A $25 coaching session is still validation for your concept, and you can work to grow from there once you have more experience and see if you like it. There's real power in getting started and seeing with your own eyes that others value your expertise and are willing to pay for it.

Insure your career

Even if you're extremely happy with your full-time job—which is fantastic—that doesn't mean you shouldn't consider building an entrepreneurial side gig.

It can be the perfect way to make some additional money, build your network, learn new skills, try out those skills in a low-risk context, and then bring that knowledge back to work on Monday. In a fast-changing economy, that's the ultimate career insurance.

How TD Professionals Can Leverage Their Side Hustle

By day, Natalie Siston is the director of sales coaching and development at Nationwide. But by night (and on weekends), she runs her own coaching and speaking business, Small Town Leadership. In her side job, she shares leadership lessons learned from growing up in a town of 600 people—and how the lessons carried her through her career, from Silicon Valley to a Fortune 100 firm.

When she started her business in 2016, Siston had fears: "What if I said something offensive? Will people question my commitment to my nine-to-five?" However, she soon realized that her business was "a place to experiment, learn, and make up my own rules." Here are four key benefits she's gotten out of her side gig.

New skills. Because she started her business from scratch with no outside help for the first two years, Siston says, "I've had to teach myself more skills in the past three years than I did in the first 15 years of my career," including web design, IT, content creation, sales, marketing, and social media.

Increased efficiency. Working a side hustle has also made her fanatically efficient with her time. "Not only do I run Small Town Leadership and work a regular job," she explains, "but I also have a family that includes two young daughters and a very busy husband who works in academia. The number 1 question I get asked is: How do you fit it all in? Managing everything has taught me to maximize my time. I can get more done in 25 minutes than I ever thought possible. I've also become a master at prioritization." Those skills carry over to her day job at Nationwide.

Better tech tools. Sometimes, corporations stick with certain technologies because it's what they've always used. But when Siston discovers something in her entrepreneurial life that she finds useful—such as videoconferencing technology, group productivity and communication tools, and email creation software—she brings it to the company's attention. "I love the tools I get to use as an entrepreneur and, as much as possible, try to bring the functionality and processes into Nationwide."

More connections. To promote her company, Siston created a blog and video series. "Not only have those videos made me a go-to person for internal recordings," she says, "but they also led to conversations and meaningful interactions with colleagues that otherwise wouldn't have happened."

Siston says the impact of her side hustle has been profound. "I would not be in the job I am in today without starting Small Town Leadership. I leverage the skills I have gained as a coach, speaker, and writer daily in my role as director of sales coaching and development at Nationwide. ... Many people believe their way out of a career rut is to drastically change jobs, quit their company, or go start something on their own. I hope my story reminds people that it starts by looking inside yourself and figuring out if there is something else you can be doing to bring that spark into your professional life."

This article is adapted from the author's book, Entrepreneurial You.

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