I'm Not a Natural Entrepreneur, But I Built a Successful Business - Here's How

These are the steps I’ve taken to build a successful freelance writing business, even though entrepreneurship doesn't come naturally for me.

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Updated May 13, 2024
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I’m not a natural-born entrepreneur. I like stability and having a work-life balance, and I’m fairly risk-averse. Despite that, I’ve managed to build a successful freelance writing business that has given me the freedom to work wherever and whenever I want and made it possible to earn more than I ever could have working for someone else.

Whether you’re hoping to learn how to start a business or simply looking for additional ways to make money, entrepreneurship can be scary. But picking up a side hustle can be one of the best ways to create the kind of life you want.

Here’s how I managed to figure out how to make money with my business without having the so-called entrepreneurial gene.

How to create a lucrative side hustle

I started freelance writing in 2013, and it took roughly five years to turn my side hustle into a full-time business. Regardless of your goal with a side business, here are some of the things I’ve learned along the way that can help you succeed, even if the process doesn’t come naturally for you.

1. Determine your why

One of the hardest things about building a side hustle is maintaining motivation. For natural-born entrepreneurs, that can come easily because they enjoy the whole process, even the challenging parts.

For me, though, it was easy to get discouraged when I got rejected or ghosted by clients, and there were many times that I almost gave up in favor of the certainty and stability of being a full-time staff writer.

Your reasons for wanting to start a side hustle are unique to you. For me, the biggest motivator was freedom:

  • The freedom to work when I want and do other things when I want.
  • The freedom to travel whenever and wherever I want.
  • The financial freedom that comes with having more control over my income.

At times, my desire for security was stronger than my motivation to build my side hustle. In fact, I spent almost two years not freelancing at all. But over time, my desire for freedom grew stronger and eventually helped me make the changes I needed to pursue my dream.

2. Focus on something you love

Freelance writing was the best side hustle for me because it combined my love of writing with my love of personal finance and travel. Although there are times that I don’t particularly enjoy what I do, they’re few and far between — plus, the freedom I’ve gained has given me the chance to pursue other business ideas without worrying about losing my stability.

When you choose something you love as a side hustle, it’s easy to spend time doing it, even if you’re not making a lot of money yet. So think about the things you’re passionate about, and consider how you might be able to turn that passion into a money-making endeavor. You may already be posting images of your passion on social media and engaging with like-minded others, so consider how to make money on Instagram with posts you're already creating anyways.

Also, keep in mind that some hobbies are meant to be just that. If you find that you start to lose your love for something as you start to make money, it may not be the best fit for a long-term business.

If you’re not sure where to start, here are some of the best side hustles to give you some ideas.

3. Face your fears

It’s completely natural to have fears about starting a side hustle. Even people who have a strong entrepreneurial spirit have fears.

But it’s virtually impossible to build a successful side business or full-time business and live the life you want without identifying and working to overcome (or at least become comfortable with) your fears. These fears may include:

  • Fear of failure
  • Fear of change
  • Fear of discomfort
  • Fear of uncertainty
  • Fear of being wrong
  • Fear of taking financial risks
  • Fear of disappointing yourself and others
  • Fear that you’re not good enough

I’ve experienced every single one of these fears on my journey to becoming a freelance writer, and I still feel some of them from time to time. But they no longer paralyze me. For me, facing my fears involved:

  • Writing them down: Identifying what you’re afraid of is the first step. Without knowing what you’re afraid of, all your anxieties and fears get mashed together and feel overwhelming. But once you know exactly what’s stopping you, it’s easier to address it.
  • Creating space for them: It’s important to recognize that your fears are internal mechanisms to help protect you from harm. They’re not inherently bad, and if you can manage to create space for them in your mind and understand why they exist, their power over you will diminish. Learn ways to practice mindfulness with your fears.
  • Taking action: You’ll likely never fully overcome all of your fears, and if you wait for that day to come, it won’t happen. It’s crucial that you start taking action despite your fears, even if it’s just one small step.

4. Start small

For a long time, I was an all-or-nothing type of person. The idea of not giving my side hustle my full attention from the start made me feel like I would be wasting time.

But if I hadn’t started small in 2013, I’d likely still be working for someone else and making far less money than I do now. Plus, starting small can help you develop the confidence you need to better manage some of your fears.

For me, starting small meant getting up an hour earlier or using my lunch break to write for clients. Over time, I increased my dedication until I was ready to take my side hustle full time. It also meant learning the mechanics of how to start your own business, so I knew what to expect with the experience.

5. Find your community

One of the best things I did was find a community early, specifically a community of personal finance bloggers and writers. Not everyone in the community is a freelance writer, but many of them have found success with blogging and other forms of content creation.

I also found a small group of freelance writers who were in varying stages of the process. Finding a community helped me because it provided evidence that my dream wasn’t crazy — other people were doing it too.

What’s more, the community provided me with support as I learned how to become a better writer and build my business.

6. Gather support from loved ones

Although having a community of people who are doing the same thing as you is important, it can be just as or even more essential to have support from your loved ones.

This step was tough for me because I didn’t always have the support I needed from the people closest to me. It made the process of building my freelancing business a lot harder than it would have been otherwise.

But if you can manage to get buy-in from your loved ones, it can help resolve some fears and make the process go more smoothly.

7. Offer support to others

As you grow your side hustle, you’ll be in a position to provide support for others in your community who are doing the same thing. I never have and never will view other freelance writers as competitors, and I’ve had the chance to share my experience and job opportunities with several others who have struggled just like me.

Offering support to others is primarily a selfless act, but it also benefits you by building trust and camaraderie in your community. It also helps expand your network, which can provide you with more opportunities in the future.

8. Don’t be afraid to invest a little

My biggest fear, in the beginning, was taking financial risks. During my first year out of college, I struggled to find a job in finance, which was my major in college, and I earned just $10,000 that year.

But I realized that I would have no chance of succeeding as a freelance writer without investing a little. That included a few hundred dollars to start a blog and another few hundred dollars to attend a financial media conference.

Ultimately, my first blog was a failure, but it helped me ease into that community. The conference, on the other hand, may be the single most important thing I could have done early on. It lit the spark that started my full-time writing career.

If you’re not sure you have the money to invest even a few hundred dollars, some of the best business credit cards offer introductory 0% APR promotions that you can use to float some of those expenses and pay them off over time interest-free. I’ve used these features a couple of times during my journey.

9. Don’t be afraid to try something new

Not everything you try is going to work, but that doesn’t mean you’re a failure. I’ve tried several different things over the years to build my business. I briefly tried writing about other topics beyond money and travel, only to realize that I wasn’t good at it and didn’t enjoy it.

I also tried starting a new money-focused blog from the perspective of the faith I grew up in. But when I decided to leave that faith, I had no desire to continue the blog.

If you don’t get your side hustle right on the first try, don’t quit. Instead, make some adjustments and test out new approaches until you start seeing the results you want.

The bottom line

Starting and building a side hustle can be a daunting task, and if you’re like me and not naturally wired for entrepreneurship, it’s easy to stick with the certainty you already have.

But with the right mindset and steps, it’s possible to build a business — whether you want to do it full time or on the side — and reap all of the benefits that come with it. What business you should start depends wholly on you and what you want to accomplish.

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Ben Luthi

Ben is a personal finance and travel writer who loves helping people achieve their money goals. Along with FinanceBuzz, his writing has also been featured on U.S. News, NerdWallet, Experian, Credit Karma, and more.