Ten Years of Side Hustling: What I’ve Learned

Randy Ginsburg
4 min readAug 26, 2020

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In a time as bleak as the COVID era, finding motivation to be productive may seem like a struggle. Just getting through the days can be exhausting. At the start of the pandemic, we all were drawn to the idea of having more time to pick up new skills or catch up on old projects. Now that this has become the new normal, it seems as if a lot of this ambition has faded. Plagued by the feeling that I may never have this much free time again, I took on a lot more work leading to periods of burnout. That being said, I’m also a large advocate of using this time to start something new. If you’ve read my book, you know my belief that life’s lowest points often serve as catalysts for great ideas. Airbnb, Uber, Square and Venmo were all launched during the recession. While I’m not saying that everyone should be working on starting a billion dollar company, I am a firm believer that everyone should have a side hustle. Even if you never intend to turn it into a full-time job.

It doesn’t need to be a money-maker, but instead a creative outlet to distract you from everything else going on in the world. Something that gets you excited and stimulated. Over the last few years, I’ve experimented with a handful of side hustles, both small and large. I often get asked about what I’ve learned from my entrepreneurial endeavors, so I thought I would share some of my biggest takeaways.

  1. Plan, then execute

The ability to execute is more crucial to success than having a good idea. But, even the best executors need a plan. Whenever you are launching something new, allot more than enough time to plan out the launch. Depending on the project, I will give myself at least four to six months to plan and ideate before releasing my work to the world. I failed to do this for my book and it made my marketing efforts significantly more challenging. Use this time to think of how you will market, distribute, and scale your product or service. Focus on building excitement and hype around it. Not all plans are meant to be adhered to, but at least this will serve as a guiding light as you move forward.

2. Everything takes longer than you think

Success doesn’t happen overnight and neither do the small wins. Whether it’s landing an interview, getting on a podcast, making your first sale or receiving payment from an existing client, nothing ever happens as quickly as you think it will. Get comfortable with waiting. I’m naturally an impatient person and this is one of the hardest things I’ve needed to learn. This goes hand in hand with counting your chickens before they hatch. Until the deal is closed, the interview is posted, payment is sent, etc. don’t speak on it. When things fall through, it undermines your credibility and leaves you looking stupid. Trust me, I learned this one the hard way too.

3. Big names don’t mean big results

I set a goal to land features in Forbes, Entrepreneur and Inc. within the first year of my book launch. Aside from using these outlets to build my credibility, I also thought it would help boost book sales. I was wrong. Finding the right person to write about your product is much more important than the name of the publication. While Forbes has a much larger audience than the Morning Brew, my newsletter feature in The Brew (which was hyperlinked in a blog post that was hyperlinked in an email) received significantly higher engagement than an article about me on the Forbes homepage.

4. Build in public. It holds you accountable.

Putting yourself out there can be scary, but creating in public is necessary for growth. Once your work is posted online, any feedback or criticism is fair game. Some of my most valuable lessons have come from random people online questioning my ideas. The more you post, the more comfortable you will be with the idea of being wrong. Posting your progress towards a goal online creates a level of transparency and authenticity that’s admired by others. Giving an inside look on what you’re building as you’re doing it is a great way to grow a following on the internet.

Publicly sharing what you’re working on also keeps you accountable. It would be a lot harder for me to continue to write two newsletters per week if I knew I was the only one receiving them. Posting about them on social media to thousands of people forces me to show up even when I don’t want to.

5. Don’t be afraid to speak to people about your ideas. When people tell you you’re crazy, that means you’re onto something good.

You’ve heard this one before. You can’t please everyone, but no one knows you better than yourself. My general rule of thumb: If my parents say it’s too risky, then I double down.

The more you speak to others about your ideas, you’ll learn who to go to for certain advice. Having people to talk things through with is a crucial part of the ideation process. It takes a certain type person to start something of their own. The likelihood that the person you’re telling your idea to shares even a tenth of the excitement towards it is very slim. Chances are they aren’t stealing your idea.

If you liked what you read, I’d highly suggest subscribing to my newsletter, Crashing Up. Here you will find a collection of ideas and insights to help you level up in both your professional and personal life. You can also follow me on Twitter here.

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Randy Ginsburg

Author of Adversity to Advantage: How to Overcome Bullying & Find Entrepreneurial Success / Follow Me @GinsburgRandy