The Struggle to Start a Side Business

I want to start a side business, i.e. earn money outside of work to complement my full-time salary. I’ve had this feeling for awhile now and am finally putting it on paper.

With the rise of companies like Facebook and Twitter, entrepreneurship has become the sexy thing to do. Everyone thinks their idea is going to be the next big thing.

Exponential user growth.

Billion dollar valuations.


Cashing in and having more money than you’ll ever know what to do with.

That’s the dream, and I want in on it (to a certain degree). You probably do, too.

While the odds of a high level of success from starting your own company are heavily stacked against you, you’ve got to remember that many of these uber-successful businesses began as side projects. As soon as they gained solid momentum, the founders quit their day jobs to pursue their ideas full-time. From what I’ve read, that’s the ideal approach to getting your idea off the ground given the financial security of a full-time job.

As happy as I am in my current job, I’m very much in tune with the idea that the modern workplace has drastically changed. Employees jump ship frequently as they get stagnant at work. Traditional companies are squeezing out the middlemen by hiring cheaper labor and automating processes through technology. It’s up to you and me to become indispensable at work but at the same time pursue interesting things and discover our true passions.

Reasons Why I Want to Start a Side Business

1. Additional Income – Some people are perfectly comfortable living off a salary. I’d much rather create multiple streams of income that allow me to live more comfortably. If I was ever laid off or quit my job, I could at least rely a little on my side business(es) to keep me afloat.

2. Entrepreneurial Tick – Since college, I’ve become really interested in startups and entrepreneurship. Through reading business books, autobiographies and industry articles as well as blogging, I’ve developed a mindset that knows that starting a business and being my own boss will be the right path for me. It’s just a matter of when.

3. Diverse Interests – Why settle for a job that only lets you practice skills in finite areas? I’m definitely interested in social media, but I am also curious about blogging, book marketing, book writing, building sustainable businesses, etc. And the list keeps growing. While it’s awesome to be knowledgable about other topics outside your job, it’s even cooler and more fun to put them to the test and earn some money for the time you’re already investing.

4. Personal Brand Development – My boss Gary Vaynerchuk says that everyone’s a media company today. I couldn’t agree more. Everything you do on- and offline shapes your reputation and legacy. The longer you work for someone else, the more you’re tying your name to that company and being overshadowed by its success and reputation. Once you become a business owner, your name is much more out there. Who you are and what you do become one and the same.

These all seem like great reasons for me to take the plunge and start a side business. However, I have my doubts. I’m only human.

I hope that by admitting them publicly and elaborating on them below, I will be empowered to start executing on ideas that might very well become side businesses.

Fears Standing in My Way

1. “I don’t have the right idea.” – Every entrepreneur is obsessed with finding that one idea that’s going to allow them to strike gold. While it might exist, 99.9% of the time it’s not going to be the first business idea you try. I must learn to accept an imperfect beginning in order to get started at all. The best way to discover better business ideas is to fail fast, learn and adapt.

2. “I’m going to fail.” – Everyone tries to avoid failure, but it really is inevitable. I definitely don’t want to be that guy who keeps starting ventures only to quit after a short time and move on to something else. As much as it might make me feel dejected, I have to acknowledge that it’s part of an entrepreneur’s DNA. There’s absolutely no shame in it. Failures should not be frowned upon but rather celebrated as learning opportunities that shape launching a future successful business.

3. “I don’t have the time.” – This is my biggest fear. Obviously, my hours outside of my full-time job are limited. It’s been really tough juggling the responsibilities that come with living in NYC with my interests outside of work (committed relationship, reading books, blogging, alumni club involvement, etc.). It’s really a matter of discipline and cutting out the things in my life that are not adding value. The best way to launch a business is really to work on it every single day. No excuses.

4. “I don’t know how to run a business.” – As a 23-year-old who thinks he knows everything about the world, there are definitely a lot of things in life that I have yet to experience and learn firsthand. While I do have natural skills and an understanding of business, I’ve never actually run one. This inexperience intimidates me, but at the same time, I realize that at some point you just have to take the plunge. Otherwise, you’ll be preparing your whole life for something that never happens and wondering where all that time went. I will learn a ton make mistakes, but I will become better because of them.

This honest self-analysis has definitely helped me put things more in perspective. I know that starting a business is something I want to do and need to take action on sooner than later. It’s time for me to man up, pick an idea, and start executing on it consistently. Sacrifices will have to be made, but it’s the only way to get myself going. I look forward to picking that idea, sharing it with you, and updating you on my progress.

Have you thought about starting a side business? What’s holding you back?

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2 Responses to The Struggle to Start a Side Business

  1. Pingback: 10 Lessons Learned from Gary Vaynerchuk | The Life of Riley

  2. Pingback: The Importance of Next Steps | The Life of Riley

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