9 Lessons From 9 Years in the Side Hustle Trenches

Take every opportunity, including the ones to learn.
9 Lessons From 9 Years in the Side Hustle Trenches
Image credit: Susumu Yoshioka | Getty Images

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Entrepreneur Leadership Network Contributor
Marketing Strategist + Content Writer
7 min read
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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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