20 Lessons From Side Hustling for 20+ Years

Michael Leonard


I was side hustling before it was cool.

At age seven my cousin and I sold lemonade at garage sales (seriously… hope you’re proud Gary Vaynerchuk).

At age 10, I sold “Mike’s Weekly Mixtape”, a CD I burnt and sold to my friends for $3 thanks to Napster and dial up internet.

At 14, I bought and sold golf clubs on eBay using my mom’s account (thanks Mom). I even sold old people’s used clubs who didn’t know how to use the internet at my local golf course. And in college, I coordinated party busses to nightclubs to afford my weekend binges.

After climbing the corporate ladder for six years, I knew I had to quit the boredom and become an entrepreneur. Finally, in 2017, I turned my side hustle of writing into a full-time business. I’m grateful to say that I’ve never had to go back to a corporate job despite battling through some very difficult times.

But I think the entrepreneur roller coaster made me that much more equipped for the craziness of 2020. During these uncertain times, I think it’s never been more important to learn how to make money with an online side hustle.

Before you jump in head first, learn from my 20+ years experience to speed up the journey to success.

20 Side Hustle Lessons

Use these side hustles to help you speed up success in 2021 and beyond.

  1. You can make money in pretty much every niche. If you would’ve ever told me that I’d make over $33,000 writing about golf I’d have thought you were crazy. And it’s been a lot more since that story was published. But it happened, proving that you can make money doing pretty much anything.
  2. Money is everywhere. When times get financially tough, it’s easy to feel like you can’t make money. But money is literally everywhere. The worst times are often the best ones if you become resourceful and keep helping others. Focus on serving (not just making money) and the money will keep flowing.
  3. You are more resourceful than you think. One of my favorite Tony Robbins quotes is “Resourcefulness is the ultimate resource.” In my experience it’s 100% true and a side hustle will bring out your inner entrepreneur. There’s a lot more potential inside you than you probably give yourself credit for. Most corporate jobs don’t really bring out our true potential and instead make us act like zombies most of the week. But when you start your own passion project, you can start to unlock your true potential. And when you start to see results, anything will feel possible and you will have more motivation than ever.
  4. People will doubt you (but secretly be jealous of you). Side hustling opens yourself up to some risk and failing along the way. This will lead to people judging you and maybe even mocking your ambition — family, friend, coworkers or all of the above. But you know what? Who cares… you’re in the game while they’re watching from the stands. Never let anyone doing less than you impact your goals — stay focused on why you started. When you make it, one day they’ll ask you how you did it.
  5. Focus on your passion. I think side hustles will turn into full-time gigs and make you a lot of money if you’re passionate about it. For example, if you hate numbers but want to start a side hustle e-commerce store, good luck staying consistent. Instead, focus on a topic you love as it’ll make it easier to keep going when you want to quit. Believe me, you will want to quit at some point.
  6. You’ll want to quit. The first part of starting anything new is really hard — whether you’re learning a new sport, starting a new hustle or switching careers. Side hustling is no different and arguably the most difficult as you’re trying to create money out of thin air. But if you love what you do, it’ll be worth it and you’ll tap into more resources than you ever thought possible.
  7. Your first $1 is so rewarding. I still remember the first $1 I made on Google Adsense on my blog. I would argue it was more rewarding than six figures I was making at my corporate job. Okay, this isn’t a lesson but I just want you to pat yourself on the back when you earn your first buck. Most people will never venture far enough out of their comfort zone like you did so take pride in your achievements.
  8. Never stop learning. After five plus years of publishing content and hustling online, I feel like I’m just getting started. The point? You never know it all. Keep learning, surround yourself with people doing what you want to do, and keep an open mind. One subtle shift can explode your side hustle into a full-time gig!
  9. Don’t try everything at once. If you’re like most side hustlers, you’re ambitious and have big dreams — trust me, I get it. But one of the biggest mistakes I made was trying to do too many hustle at the same time. At one point, I was blogging, writing, running an E-commerce store, starting a podcast, and more. Needless to say, this didn’t work well as my time was spread thin. It’s hard to be really good at tons of different hustles. Instead of being scattered, pick one side hustle for 90 days and run with it.
  10. Set goals. A lot of times side hustles start out as fun which is great — but if you want to earn consistent money from it, start setting goals asap. As Peter Drucker said, “You can’t manage what you don’t measure.” Once you have a tangible revenue goal you can make a plan, track your metrics, and make adjustments as needed.
  11. Never get attached to your goals. Let me be 100% clear, setting goals is highly encouraged but never get attached to the outcome. If you don’t hit your goals, do not attach your identity to it. I did this so many times that I found it demotivating and would take long breaks on certain projects. Instead, pick a stretch goal and reverse engineer what you need to do to make it happen. Once your time period for the goal is over, review if you took action and what you learned more than the outcome itself.
  12. Schedule your time intentionally. Life gets busy with family, work, and everything else going on. If you really want to make your side hustle work, you need to schedule your time in advance. Whether it’s in the morning, evenings, weekends or a combination, create a side hustle schedule and stick with it. Otherwise, it’s easy to slack off for a few days and weeks until your side hustle is just an expensive hobby or fizzles out.
  13. Expect to win. So many people play to lose in life and business because our mind is wired for negativity! Every time I go into a new hustle, I always have the mentality that I’m going to make it. Even though the odds are stacked against me, I believe in it working out (or teaching me a lesson I need to learn). Think about it, the odds of you being born are even smaller, so why can’t your side hustle work?
  14. Find a mentor. Success always leaves clues. Whatever hustle you’re doing, chances are, others have done it as well. Instead of going at it alone (the hard route), find a mentor. Study people who are ahead of you by buying their books, listening to podcasts, or joining their programs. Remember, mentors don’t always need to be in person to be effective and help you get the desired results.
  15. Keep going. Your side hustle is a marathon, not a sprint. So many people I meet try it out for a few weeks or months, don’t get results they want or expect and quit. Are you kidding me!? You have to stick with it, test out all kinds of ideas, learn to love failure, and finish the race.
  16. Quit hustling. Most people will tell you to hustle more but I think it’s that total BS. I know that hustling is literally part of the word side hustle but please don’t buy into it. While you do need a good work ethic, I think you need to quit hustling. I’ve burnt out several times from working too many hours and trying to do it all myself. This almost led to me quitting entrepreneurship entirely. Don’t forget, mental health is more important than money.
  17. Ask your subconscious mind. Anytime you try something new, you’re likely to get stuck and have no clue what to do next. Instead of trying to figure it out through sheer will, relax and ask your subconscious for some help. Here’s the thing, everything you want and need is inside of you. But it’s up to you to get it out. One way to do that is to ask your subconscious mind a question before a nap or going to bed. Because as you sleep, it’s still working 24/7/365 to keep you alive and function properly. Request an answer and expect it to happen… you might get the next steps when you wake up or in the coming days. I find that in quiet moments, like driving, showering or meditating the answer seemingly comes to me. But it will never happen if you don’t believe it can happen.
  18. Get help. Most side hustlers start out as a solopreneur — doing everything in their business. I did this for years but once I hired my first virtual assistant, everything changed. It’s hard to do everything yourself as you scale so don’t be afraid of hiring freelance and virtual assistants to help with tasks you hate doing. This will not only save you time but precious energy which you can use to keep growing.
  19. Have fun. I know it sounds cliché but seriously, enjoy the process. If you don’t, it’ll start to feel like a job that you dread. This will lead to lower motivation levels, less impact, and likely less money!
  20. Celebrate your wins. A win is a win, so make sure you celebrate them (regardless of size) so you keep programming your mind for success!

Final Thoughts

While I got started as an entrepreneur early, I’m convinced that no one is born entrepreneurial. I’ve seen friends never have a hustle until they were in their 20s or 30s and eventually make it work.

All you need is a desire to make it happen. As Napoleon Hill said,

“There is nothing that belief plus a burning desire cannot make real.”

With all the uncertainty in the world, it’s up to you to start your own side hustle so that you can control your destiny. It’s never been simpler to get started so get out there and make it happen.

The sooner you start, the sooner you’ll thank yourself. You can’t lose when you bet on yourself!

Photo by VikaOvcharenko on Deposit Photos

Comments / 0

Published by

My name is Michael Leonard and I am the creator of Inspire Your Success. I'm on a mission to help readers build online writing businesses and quit their jobs to live a life of freedom!

Scottsdale, AZ

More from Michael Leonard

Comments / 0