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9 Lessons From 9 Years in the Side Hustle Trenches



October 13, 2020 7 min read

Opinions expressed by Entrepreneur contributors are their own.

Half of Americans have a “side hustle“— a job in addition to their full-time career. It might have a new(ish) moniker, but it’s not a new phenomenon. Adults have been side-gigging, freelancing, and hustling for decades. , the accessibility of modern technologies, and a shift to remote work have made starting a side hustle easier, faster, and less expensive. If you’re hustling for work on the side, regardless of the industry, two things are likely true: You’re good at it, and you enjoy it. According to a BankRate study, more than one in four people who pursue a side hustle are more passionate about that side job than they are about their careers. And while passion doesn’t necessarily translate to dollars, it can make you more successful overall, according to Investopedia

More than 60 percent of people have had a side hustle at one point or another. If you’re considering a side hustle, or want to turn yours into a full-time career, take advice from those who’ve come before. I’ve been side hustling as a writer since 2004, but I wasn’t able to turn it into a career until 2013. Here’s what I learned in those nine years.

Related: 50 Ideas for a Lucrative Side Hustle

1. Speak up

The moment I decided I wanted to be a freelance copywriter, I started talking about it. About one week in, I was at my son’s little league game when one of the other moms came over and asked how I was doing. “Great,” I told her. “I’ve started my freelance and it’s going really well. How about you?” After asking about my business, she told me she was the VP of for a national company and that she’d love some help with a new brochure and website. “Is that something you can do?” she asked. Her company became my first client and remained one of my largest for the next 12 years. 

2. Networking is to business what location is to real estate: everything

Reach out to those you admire in the industry. People love to talk about themselves so let them! Ask them about how they got started, how they determine their hourly rates, their process, their billing cycle, their biggest mistake, their smartest move, etc. Show them your work, ask for their advice and be ready to take criticism and learn from it. Remember, everyone you know knows someone. Connect as often as possible, in-person and online. 

3. Never stop selling

The minute you stop selling your business, you’ve lost. No matter how busy you get, you can’t take a break from looking for new business. Earmark a specific day and timeframe each week to focus exclusively on new business. No matter how preoccupied I am with clients and projects, I make time every Monday morning to send emails, share posts, rand each out to potential clients. Existing clients need to be included in this effort, as well — so take time to reach out, touch base and connect to continue building those valuable relationships. 

4. Give it away (once or twice)

One of the agency owners I met with suggest me I offer to do an assignment free of charge. A few weeks later, an opportunity presented itself: A distant relative opened a pizza franchise in Wisconsin and needed a press release. I offered to write it pro-bono. That press release earned him placement in three newspapers as well as a live NPR interview. I’ve written countless press releases since, thanks to the success of that first assignement. 

5. Always learn or teach

One of my favorite sayings comes from CEO : “The learn-it-all does better than the know-it-all.” The proliferation of social media and content have created a of know-it-alls — don’t be one of them. Be constantly curious and think like a start-up every single day. If you’re not learning something, you should be teaching it. When you’ve learned something valuable, share it! Write an article, hold a webinar, speak at a conference, or volunteer to guest lecture at a local university. Not only will you be helping others, but you’ll also help your own business through networking. If you’re neither learning nor teaching, you’re stagnant, and your business — and you — will suffer.

6. Find your unique angle

I spent the 90s in the ad agency world. At that time, agencies would take on any project. Sales promotions agencies were planning VIP events, experiential agencies were running sweepstakes, and ad agencies were managing mobile tours. It didn’t seem to matter what their capabilities were; they just wanted the revenue. Take it from the 90s (where a lot of agencies died): You can’t be everything. My first client was in the B2B remodeling industry, and while I tried to branch out to every industry, most of the clients I worked with in those first few years fell into that vertical. Rather than focus on remodeling, I learned to tout the “B2B” aspect of my experience and that allowed me to get into the growing industry of B2B tech content. Soon after, my work in the remodeling sector led B2C remodeling companies to me, which led to parallel industries such as home improvement, plumbing, flooring, and real estate. Today, I work almost “exclusively” with the broad category of service-based businesses. 

Related: Is Focusing on a Specific Niche Really That Important?

7. Recognize opportunity (and say ‘yes’ to it) 

I wanted to work for myself full time, but when presented with an opportunity to run a department, I couldn’t say no. That position opened me up to more experiences, global brands, and new skill sets I wouldn’t have had otherwise. Still, I didn’t give up my side hustle. That meant working long hours day and night for a few years, but it definitely paid dividends in the form of hundreds of new connections, high-profile projects for Fortune 500 brands, and dozens of clients. 

8. Get comfortable with being uncomfortable

Stepping outside your comfort zone is the only way to grow. I’m not a , in fact it makes me nervous just to make eye contact when speaking with more than one person at a time. I’m not a fan of being on stage, so I do it every chance I get. I’ve spoken on stage at three industry conferences and in front of classrooms filled with college students. It’s still a bit terrifying, but it always leads to new connections and I get a bit better at it each time. 

9. Don’t burn bridges

In business, as in life, you won’t gel with everyone. Companies evolve, employees move on, and brands change their marketing strategies. Sometimes you’ll be caught in the crosshairs. The best advice I can give you is this: Once a client, always a client. While you might be inclined (or forced) to end a business relationship, never let go of those connections. I’ve had contracts end suddenly only to be brought back months, and in one case even years, later. The only way to ensure you’ll have future opportunities with a former client is to be a bridge. LinkedIn is a great tool for staying in touch and top of mind.

Related: Why You Fear Public Speaking and How to Overcome It


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Iowa Never Locked Down. Its Economy Is Struggling Anyway.



As far as the law is concerned, there is no reason that Amedeo Rossi can’t reopen his martini bar in downtown Des Moines, or resume shows at his concert venue two doors down. Yet Mr. Rossi’s businesses remain dark, and one has closed for good.

There are no restrictions keeping Denver Foote from carrying on with her work at the salon where she styles hair. But Ms. Foote is picking up only two shifts a week, and is often sent home early because there are so few customers.

No lockdown stood in the way of the city’s Oktoberfest, but the celebration was canceled. “We could have done it, absolutely,” said Mindy Toyne, whose company has produced the event for 17 years. “We just couldn’t fathom a way that we could produce a festival that was safe.”

President Trump and many supporters blame restrictions on business activity, often imposed by Democratic governors and mayors, for prolonging the economic crisis initially caused by the virus. But the experience of states like Iowa shows the economy is far from back to normal even in Republican-led states that have imposed few business restrictions.

A growing body of research has concluded that the steep drop in economic activity last spring was primarily a result of individual decisions by consumers and businesses rather than legal mandates. People stopped going to restaurants even before governors ordered them shut down. Airports emptied out even though there were never significant restrictions on domestic air travel.

States like Iowa that reopened quickly did have an initial pop in employment and sales. But more cautious states have at least partly closed that gap, and have seen faster economic rebounds in recent months by many measures.

ImageCourt Avenue in downtown Des Moines attracted little foot traffic on a Saturday night in October.
Credit…Kathryn Gamble for The New York Times

Economists say it is hard to estimate exactly how much economic activity is still being restrained by capacity limits, social-distancing rules and similar policies, many of which have been lifted or loosened even in places governed by Democrats. In most states, restaurants, retail stores and even bars are allowed to operate.

Perhaps the most widespread government action that has hindered economic growth is the decision by many school districts to adopt virtual learning at the start of the school year, which appears to have driven many parents, particularly women, out of the labor force to care for young children who would otherwise be in class.

But as the pandemic flares again in much of the country, most economists agree this much is clear: The main thing holding back the economy is not formal restrictions. It is people’s continued fear of the virus itself.

“You can’t just open the economy and expect everything to go back to pre-Covid levels,” said Michael Luca, a Harvard Business School economist who has studied the impact of restrictions during the pandemic. “If a market is not safe, people won’t participate in it.”

Iowa was one of only a handful of states that never imposed a full stay-at-home order. Restaurants, movie theaters, hair salons and bars were allowed to reopen starting in May, earlier than in most states. Gov. Kim Reynolds has emphasized the need to make the economy a priority, and has blocked cities and towns from requiring masks or imposing many other restrictions.

Even so, Iowa has regained just over half of the 186,000 jobs it lost between February and April, and progress — as in the country as a whole — is slowing. Many businesses worry they won’t be able to make it through the winter without more help from Congress. Others have already failed. Now, coronavirus cases are rising there.

Vaudeville Mews, the small performance hall that Mr. Rossi opened in Des Moines in 2002, was a labor of love even in the best of times. The venue attracted a fan base with its willingness to book independent acts, but it often lost money. Mr. Rossi had been saving up in hopes of buying a new space, but the pandemic ended that dream.

Legally, music venues in Iowa were allowed to reopen in June, but with social-distancing requirements that significantly reduced their capacity. Even if those rules were lifted, Mr. Rossi said, he couldn’t see a path toward reopening safely and profitably anytime soon. This month, he announced that Vaudeville Mews would be closing permanently.

“We couldn’t pay our rent, and it was piling up, and we were constantly still getting drained by internet bill, insurance bill, utility bill,” he said. “Who wants to go into huge debt to float a business that we don’t see any end in sight?”

Mr. Rossi’s nearby bar, the Lift, is officially still in business, but aside from a brief experiment with deliveries, it hasn’t served a drink since March. He has considered welcoming a small number of customers on a reservation-only basis, but so far hasn’t figured out how to reopen in a way that would both be safe and not cost him even more than staying closed.

Credit…Kathryn Gamble for The New York Times
Credit…Kathryn Gamble for The New York Times

“We felt it would be worse for us to reopen,” he said.

At Court Avenue Restaurant & Brewing Company, around the corner from Vaudeville Mews and the Lift, the lack of nightlife is taking a toll on business. So is the lack of the normal lunchtime crowd, with many office employees still working from home. Court Avenue reopened in May, but has regained just 30 to 40 percent of its pre-pandemic sales, according to the owner, Scott Carlson.

“Even if the governor said, ‘Hey, we’re taking away all restrictions and all mandates and all recommendations,’ our numbers wouldn’t change, not very dramatically,” he said.

Iowa has outperformed many other states economically during the pandemic, at least by some measures. The unemployment rate capped out at 11 percent in April — below the 14.7 percent hit by the country as a whole — and it has fallen quickly, to 4.7 percent in September.

But economists attribute Iowa’s success primarily to its favorable mix of industries. The state relies more heavily than most on agriculture and manufacturing, which were comparatively insulated from the virus.

Vulnerable industries like tourism, hospitality and retail sales are struggling in Iowa as they are everywhere else. Data compiled by researchers at Harvard and Brown Universities from private sources shows that consumer spending has rebounded more slowly in Iowa than in neighboring states.

“Retailers are still having a tough go of it in Iowa,” said Ernie Goss, a Creighton University economist who studies Iowa and the Midwest. “You’re talking about individuals who regardless of regulations are not going back in a restaurant right now.”

Mike Draper owns a chain of T-shirt shops with three stores in Iowa and others in Omaha, Chicago and Kansas City, Mo. Customer traffic is down 30 to 50 percent in all of them, he said, with no consistent patterns based on the rules local governments have imposed.

“It has almost nothing to do with regulations,” Mr. Draper said. “It’s really driven by people’s mentality more than regulations.”

Credit…Kathryn Gamble for The New York Times

There is little doubt that restrictions are restraining some economic activity, particularly in parts of the country that have strictly limited restaurant capacity and indoor gatherings. Local business owners say that restaurants are noticeably busier in Davenport, Iowa, than across the Mississippi River in Moline, Ill., where rules on mask-wearing and social distancing are stricter and more consistently enforced, although business is not back to normal on either side of the river.

But greater activity can also come with a cost, to both public health and the economy. When college campuses in Iowa reopened in August, students packed into bars and nightclubs — and coronavirus cases quickly began to rise. Governor Reynolds shut down bars in several college towns for more than a month.

For some workers, Iowa’s situation is the worst of both worlds: They are back at work, putting them at risk of contracting the virus, but don’t have enough customers to make a living.

Credit…Kathryn Gamble for The New York Times
Credit…Kathryn Gamble for The New York Times

Ms. Foote, 24, had worked at the beauty salon for just a few weeks when it shut down because of the pandemic. The job was the fulfillment of a longstanding dream — after years of juggling school and low-wage jobs, she was finally working full time and on track to get benefits.

Even so, when the salon reopened in the spring, she was scared to return to work. And once she did go back, there was little work for her.

“I just kind of sit around and don’t do anything,” she said. “People are scared to go into the salon and sit for an hour.”

Ms. Foote said she was taking home just $200 for each two-week pay period, meaning she again needs to supplement her income with part-time jobs. But she isn’t sure she should be rooting for business to pick up.

“I don’t see how me going to the salon more often and exposing myself is going to make things better,” she said. “I don’t think that’s safe, personally.”


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The pandemic is upending job seekers’ plans, and states’ support systems.



John Michael Purdon is temporarily working as a substitute teacher near his home in Barnegat, N.J., but that was not the plan. Mr. Purdon, 22, graduated in April from the University of Pittsburgh and expected to be in a nursing residency at the Children’s Hospital of Philadelphia, “but right now, hospitals don’t have the money.”

On June 1, before he found the teaching gig, he applied for unemployment benefits. They didn’t arrive until the end of August, he said.

In his view, the economy is faltering in part because of the government’s mismanagement of the coronavirus pandemic. “I’m a health care professional myself,” he said, and “certain things were overlooked in trying to rush the economy back too quickly.”

Mr. Purdon voted for President Trump in 2016 but said he had already cast a vote for Mr. Trump’s 2020 opponent, Joseph R. Biden Jr.

States around the country, overwhelmed by applications, have struggled to deliver benefits to laid-off workers.

California, which had reported the highest number of claims, stopped accepting new claims for several weeks while it revamped its system to whittle down the backlog and to institute fraud-prevention measures.

The Labor Department’s report on jobless claims, which aims to summarize information provided by the states, is the best official accounting available, but it is a flawed estimate. During California’s hiatus, for example, officials used the last reported figure as a place holder.

States also have different accounting methods, some applicants may be double counted, and there have been reports of widespread fraud — particularly in the federal Pandemic Unemployment Assistance program, which Congress approved in March for freelancers, the self-employed and others ordinarily ineligible for state benefits.

This week, the Justice Department said it had brought 12 cases of fraud or money laundering related to unemployment insurance. State prosecutors have also brought cases.


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A two-track recovery: those returning to jobs and those who don’t expect to.



People laid off or furloughed because of the pandemic increasingly fall into two categories: those who have returned to their old jobs, and those who doubt they ever will.

Just over half — 53 percent — of those who lost jobs during the coronavirus crisis have returned to work, according to a survey conducted this month for The New York Times by the online research firm SurveyMonkey. That is up from 38 percent in August, and it is consistent with government data showing that the United States has regained a bit more than half the jobs lost last spring.

Among those still out of work, however, just 39 percent say they think they will go back to their old jobs.

The gap between the two groups is stark. People who have returned to work say their finances have held up relatively well, and they are about as optimistic as people who never lost their jobs. Nearly one in four say their finances have improved in the past year, a possible reflection of the stimulus checks and extra unemployment benefits that helped workers early on in the pandemic.

Most who are still out of work, however, say their financial situation is worsening. A third say that their unemployment benefits have expired, or that they tried and failed to get benefits. As a group, the unemployed are pessimistic not just about their finances but about the economy as a whole.

Economists say those workers are right to worry. In a speech on Wednesday, Lael Brainard, a Federal Reserve governor, warned that as more layoffs become permanent, job growth is likely to slow, as it has begun to do.

“The job-finding rate for those who are permanently laid off is less than half the rate of those on temporary layoff,” Ms. Brainard said, “so the speed of labor market improvement is likely to decelerate further if these trends continue.”


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