I wish I was half as smart now as I was at 16!
But learning everything you don’t know is part of the process.
One thing I love about my work is I feel like I learn new things every day. Sometimes they’re small little tweaks and hacks, and other times they’re broader strategies or ideas.
I originally drafted this list 10 years ago, after my 30th birthday, and have updated it several times since then.
For context, that was pre-Side Hustle Nation, pre-podcast, pre-kids, and pre-almost everything I’m working on now. I’d been a full-time entrepreneur for 4 years already at that point, but my business had seen lots of ups and downs.
Turning 30 hit me harder than I expected it to, and I’m guessing it was because I really wasn’t where I wanted to be. I’d been battling with flaky developers, fighting with the state Assembly in Sacramento over affiliate marketing tax laws, and we were in the process of short-selling our home — which had been a major source of stress.
Ten years later, that stuff is thankfully in past, and I’m in a much better place today.
That’s not to say I’m completely stress-free, but turning 40 wasn’t so bad. I’m incredibly fortunate to have a healthy family and to get to work on stuff I love every day. Each year that goes by makes me more and more aware of that fact.
But the life I have today didn’t happen overnight. It’s the result of literally decades (well, at least 2) of entrepreneurial education, trial and error, hustle, and if I’m being totally honest, luck.
In any case, here are 40 life lessons I’ve picked up in my 40 years on this planet.
1. There are only 2 ways to get rich.
Make more, or desire less.
2. The best opportunities aren’t visible until you’re already in motion.
I have Ryan Finlay from episode 72 of The Side Hustle Show to thank for this one. Although I don’t think I fully understood the advice at the time, I’ve come to see it hold true over and over again, both for myself and for my fellow entrepreneurs.
It’s physics: an object in motion stays in motion. Once you get moving down the entrepreneurial path, no matter how feeble those first few steps are, it’s tough to stop.
- This website is the direct descendant of an old personal blog I had.
- That blog was inspired by a friend of mine I hired to help with SEO for my shoe business.
- The shoe business was born out of an internship I had in college.
- Another friend pointed out that internship job posting because he knew my other one was over.
In another branch of the side hustle tree:
- I started a freelance editing business on Fiverr.
- I learned about selling on Fiverr from an interview on the podcast.
- I knew about Kindle publishing because I’d self-published a few books.
- I self-published my first book because I wanted to make a website of mine appear more authoritative.
- I first built that website after getting inspired by a similar site in a different niche while researching yet another website.
These words from Ryan are probably the “#1 tip” I return to most often.
Start today. You never know where it will lead you!
3. Want to “make money online”? Help someone.
There have volumes of content written about how to make money online, but the simplest answer is usually the one that gets overlooked: help someone.
I’m reminded of The Rule of the Internet, which was explained to me by Jim Kukral at a conference a few years ago. He said, “People are only ever online for one of two reasons: to solve a problem, or to be entertained.”
I think solving problems is generally easier (and perhaps less competitive) than being entertaining, so what problem(s) can you solve?
Money only follows value. Like Zig Ziglar said, “You can have everything in life you want, if you will just help other people get what they want.”
4. You vote your priorities with your time.
My most common excuse for not getting something done has historically been, “I didn’t have enough time.”
What I’ve tried to replace that with is the more honest, “I prioritized something else.”
Time is our most valuable asset, and it’s a uniquely egalitarian asset in that everyone has the same 24 hours each day.
Related: How to Unlock an Extra 2 Hours a Day
5. No one bats 1.000.
What I mean by that is not everything you try is going to be a success.
(For those unfamiliar with baseball statistics, a batting average of 1.000 means getting a hit every time. Some of the best players in history hit .300, essentially failing 7 times out of 10.)
I’ve had plenty of failed projects a long the way. Some were expensive mistakes and lost me a lot of money, and others just cost me my time.
Don’t let the fear of failure stop you from stepping up to the plate, because one thing’s for certain: if you never swing, you’ll never get a hit.
And here’s the other thing about failing: it’s usually not life-threatening.
6. Plane tickets are my favorite things to buy.
Perhaps you’ve heard the quote “travel is the only thing you buy that makes you richer.” While it’s definitely not the only thing you can buy to improve your life, it is one of my favorites.
In the last 10 years, we’ve been fortunate to travel quite a bit both domestically and internationally. And the trips are exciting, but the cool thing about buying plane tickets is you get to look forward to that trip for months.
And now the cool thing is being able to meetup with fellow side hustlers and “Internet friends” nearly everywhere we go.
Related: We often fly and stay for free thanks to this one spending habit.
7. When it comes to people, no matter where you go, we’re more alike than we are different.
Most of us have the same desires and motivations all around the world.
This has been helpful to realize in a time when everything seems so polarized.
8. That said, no matter what you do, some people are just jerks.
Do your best work and don’t stress the haters and the trolls.
As someone — and maybe this sounds familiar — who generally prefers to be liked over disliked, this was a tough one. But as T. Swift would say, haters gonna hate and you just gotta shake it off :)
I used to get pretty upset over someone leaving me a bad review or calling me names online. And I’d be lying if I said it still doesn’t bother me a little, but the kind notes and thank yous I receive far outnumber and outweigh those.
I even created a “hate mail” label in my Gmail so I can archive some of the more colorful messages I get. I tell myself they’re probably just having a bad day.
Important note: Constructive criticism like I ask for in my member surveys is actually really helpful. I’ve made several changes in response to those notes.
9. Choosing what’s next doesn’t mean choosing what’s forever.
In the past, I think I assigned an unnecessary permanence to certain decisions.
For instance, I naively thought I might run my original shoe business forever.
But in other areas, I went into jobs and projects positioning them as experiments in my head. I knew I didn’t want to stay at Ford forever before I even started, but it was what was next.
Similarly, that’s opened the doors to play around with other side hustles and have fun with them knowing that if they don’t work or I don’t enjoy them, I don’t have to keep doing them.
10. The journey is the destination.
So the shoe business I mentioned above? That was my original side hustle, but after 10 years, it had reached the end of its lifespan.
It had a great run and was the vehicle that allowed me to quit my job, but it was time to move on.
I think every business (and human) has a lifespan — some longer than others of course — and while there are things you can do to extend the longevity, nothing lives forever.
That’s why I say the journey IS the destination. You’ve got to learn to love process, the ups and downs and twists along the way because every time to get where you’re going, the same question always looms: what’s next?
11. Get while the getting’s good.
In hindsight, knowing that the business wasn’t going to last forever, I wish I’d scaled up faster. I could have brought on help earlier to help accelerate the growth, but I figured I had plenty of time — and probably had some control issues too.
But I see people taking this lesson to heart on platforms like Amazon FBA. The opportunity might not last forever, but they’ve found something that works right now and are going hard to build their business while it does.
12. If there’s a shortcut, it’s mentorship.
For years and years, I was a hermit.
I was heads down, working on my business, with very little interaction with the outside world. I was stubborn, but resourceful, I told myself — every challenge that came along — I can figure this out.
That attitude was at least better than giving up and throwing in the towel — but I’ve come to recognize there’s a 3rd option that involves less brute force effort and can shorten the learning curve for almost any task. And that’s mentorship.
Instead of trying to figure everything out myself, I now ask, what I learn from the people who’ve gone before me?
Masterminds have been a huge gamechanger for me, and it’s kind of crazy to think a few years ago I had no idea what they were. But that changed, and those groups have been really helpful for accountability, feedback, support, and friendship over the years.
The entrepreneurial road can be lonely, and a peer group or mastermind group of people walking a similar path and make sure everyone gets where they’re going a little faster.
13. When the work sucks, it’s time to move on.
If your side hustle gets to the point where it just drags on you, why keep it going? The last thing you need is a second job you hate.
I’ve pulled the plug on several projects because I just didn’t enjoy working on them. Some where money-makers and some weren’t performing that well, but the common ground was there were other projects I could prioritize that were more exciting, rewarding, and fulfilling.
Like the podcast.
14. You can’t expect to get better without practice.
I don’t play much golf anymore, but when I did I’d constantly berate myself for not improving.
Then it hit me: why did I expect to get better? It’s not like I’d been practicing or hitting the driving range consistently since the last round I played.
The same is true with business. You’re probably not going to be awesome at it your first time out, but you will get better with practice.
15. Dogs are awesome.
I was never “a dog person” growing up, and as a young adult and aspiring entrepreneur, the last thing I wanted was another responsibility to take care of.
Ten years later, the “side hustle shih tzu” is an irreplaceable part of our family. He doesn’t get as much attention as he used to, but the place feels empty without him and I think having him around the house has been great for our boys.
16. Everyone is self-conscious about something.
Too fat, too thin, too hairy, too bald, too short, too tall, my voice sounds weird, my car’s a mess, my clothes don’t fit. Whatever it is, we’ve all got our own insecurities.
The good news is, most people are too worried about themselves to even notice yours.
17. It’s OK to marry your high school sweetheart….
…but there’s no need to rush into things.
Bryn and I started dating our sophomore year of high school, when I was 16 and she was 15.
Eleven years later, we finally tied the knot in top secret-fashion at San Francisco City Hall. (A few months later friends and family joined us for an awesome sham-wedding weekend in Cabo.)
I love having such a long history and having grown up together. She’s been super-supportive of all my crazy business ideas and has built a pretty sweet side hustle herself.
In college, when I was debating taking this house painting “internship,” she encouraged me to give it a shot.
“So what if it sucks?” she asked. “It’s 3 months of your life.”
And you know what?
It did suck.
But it was also amazing and eye-opening and a really important experience for me.
One thing that did take us a while to fully embrace is that when it comes to finances, it’s a team sport. To this day we actually still have separate accounts, but they really are in name only. When we learned that early retirement was even a thing, we both got really excited and began tracking our household net worth.
Related: You can use a free tool like Empower to track yours.
18. Millennia of biology aside, babymaking will never be a “rational” decision in the 21st Century.
I wrote this years before our sons were born and still stand by it.
Our little hustlers are by no means the product of rational decision making, which is why I think we had such a hard time making it.
We are spreadsheet people, through and through, and the “cons” column on our pros/cons list was quite a bit longer! I mean, kids cost time, money, and freedom — and sleep — 4 things we happen to value quite a bit.
So we justified the choice by chalking parenthood up to being part of the adventure of life and the hope he’d make our lives happier (despite boatloads of scientific evidence to the contrary) and the rest of the world a better place.
In the end, we’ve concluded that parenthood amplifies happiness. The highs are higher and the lows are lower — and both more frequent.
19. But kids are pretty awesome too.
It’s been a blast watching the boys grow and learn more every day. They are both sponges to the world and it’s fascinating to see everything they pick up on.
Being a parent has given me a lot of new perspectives, including to appreciate life’s little pleasures, moments of calm, and a newfound respect for all the sacrifices my parents made.
20. Control the controllables.
In our house we have a saying: “the weather in Turkey.”
Bryn actually came up with this while we were getting ready for our trip to Istanbul a couple years ago, as I was getting stressed about rainy weather on the 10-day forecast.
Since then, we use it to redirect focus on things you can control (what you pack) vs. the things you can’t (the weather).
(It actually ended up being beautiful there!)
It’s also helpful if you or partner find yourself freaking out about politics, current events, or other market conditions. It’s all just weather in Turkey and all you can do is control what you can control.
In a sense, “control the controllables” is the driving point behind Side Hustle Nation. You never know what outside forces will do your livelihood, so it’s best to be proactive and take matters into your own hands and your own hustle.
21. It’s just a game.
When it comes to sports, winning is more fun, but in the end it’s just a game. And the same is true for most of the stuff we stress about.
I used to be super-competitive in academics, in business, and in sports — not that I was ever very good — I just took losing personally and wanted to do better.
It took some humbling experiences in all of those areas to teach me to zoom out a little bit and understand if I put in my best effort and someone else beat me, good on them.
22. To say yes, you gotta say no.
Everything has an opportunity cost. When you say yes to something, you’re inherently saying no to something else.
I’ve been trying to get better about using Derek Sivers’ decision making framework: If it’s not a “hell yes!”, it’s a “no.” That’s actually been helpful and has made me more mindful of the projects I take on, the pitches I accept, and the meeting invites I put on the calendar.
Lately I’ve been using my own Progress Journal to help identify my top priorities and track progress toward them.
23. If you don’t take care of your body, where will you live?
Your body and your mind, which it carries, are probably some of your most important tools. Doesn’t it make sense to prioritize their maintenance, health, and wellbeing?
Take care of yourself. That means fuel, hydrate, move, and rest.
When I’m disciplined about these things, I feel 10x better and am way more effective as a business owner and a parent.
Related: My HealthyWage review: Could you get paid to lose weight?
Related: Can you turn exercise into an income stream? Here are some creative ways to get paid to walk.
24. Willpower is easier when you play offense.
Playing defense with willpower all day is exhausting! If I had to pass a bowl of M&M’s every time I got up from my desk, they wouldn’t last long.
But they’re not there — play a little bit of offense to save yourself from hours or weeks of agonizing defense.
- If you want to stop eating sugary processed food, stop bringing sugary processed food into the house.
- If you want to drink less, don’t keep beer in the fridge.
- If you want to exercise more, put your gear right by the bed.
For more on willpower, definitely check out my chat with Derek Doepker.
25. If you speak with confidence and conviction, people will believe you.
Unfortunately it works even when it’s BS; politicians are excellent at this.
But speaking with confidence is another one of those things that comes with practice. I hope if you go back and listen to the first few episodes of the podcast and compare them with the ones from 6 years later, you’ll hear an improvement.
I may not have felt very confident when I was up on stage, but it took a certain degree of confidence to land my TEDx talk in the first place.
“Do you have any speaking experience?” the organizers asked.
“Well… I have a podcast,” I said, and went on to explain the perspective I could bring to the event.
26. The things you own end up owning you.
Clutter stresses me out. It costs money, it’s a pain to move, and it takes up mental bandwidth. But beyond that, owning a bunch of stuff can really hinder your happiness, especially if it’s nice stuff.
Over the past few years, I’ve tried to implement a couple strategies for making new purchases:
- The 30-day waiting period. Next time you’re thinking of buying something, sit on it for 30 days.
- Buy higher quality. When I do buy something new, especially clothes, I’ve shifted to spending more upfront for something higher quality that I really like, fits well, and will last.
To get rid of the unnecessary possessions in your life, and even make some money in the process, you can use a couple framing questions:
- Would you buy it again?
- Have you used it in the last year?
- Could it be easily and inexpensively replaced?
Now it’s not like I’ve gone full minimalist, but I’m just trying to be more conscious about bringing new possessions into the house.
27. No one else is going to do it for you.
This one took a while to really sink in.
I’d have items on my to-do list for weeks at a time, and finally I’d realize they were only ever going to get done if I did something about it.
What that means is taking responsibility for your own life and financial well-being, becoming your own boss, and not relying on your parents, the government, or your employer.
Nobody else is going to do it for you.
28. You can’t do it all yourself.
Or maybe better said, you shouldn’t do it all yourself. I’ve been working on improving my delegation skills for years, and still have a long way to go. But I know this: I’m in a better place today, because I’ve been able to let go of certain tasks and projects.
Sometimes there are people better suited to the job. Other times there are better things I should be doing with my time.
Look at hiring not as an expense but as an investment. Think of yourself buying time, as John Jonas put it in our episode on hiring virtual assistants.
It’s hard to imagine a better thing to invest in.
29. The second best way to prevent a hangover is Vitamin B.
The best way of course is not drinking. Shocking, I know.
Also, if you “need” a drink after work, you “need” a different job.
30. Generally speaking, the majority of subject matter in school is silly.
I use the facts and formulas I memorized for school approximately never. And this is coming from a former valedictorian.
What I’ve realized is that formal education is more about learning how to learn and communicate. Those are skills I use every day.
Those lifelong skills will always be more important than memorizing passages of Hamlet or writing in cursive.
31. It’s hard to believe, but some people don’t like Jimmy Buffett.
- “If we weren’t all crazy, we would go insane.”
- “Wrinkles only go where the smiles have been.”
- Pretty much all of Cowboy in the Jungle.
32. The sound of snow falling is the best music in the world.
I love it. I think I want to experiment living in the mountains.
33. Perfection is the enemy of good enough.
I used to be much more of a perfectionist, but I’ve since learned that good enough is good enough. Striving for perfection is a recipe for disappointment, procrastination, and failure to launch.
Now that doesn’t mean you shouldn’t care about your work, just recognize that you can still help people and still make money with something that’s still imperfect in your mind.
In the words of Reid Hoffman, the founder of LinkedIn, “If you’re not embarrassed by your first product, you launched too late.”
34. In the grand scheme of things, if you’re reading this, you’re probably very fortunate.
You’re literate, have Internet access, and have at least a few free moments in your day. That’s a really powerful combination toward building a successful side hustle.
Related: For more perspective, check out GlobalRichList.com.
35. It’s OK to not know what you want to be when you grow up.
I still don’t!
Blogger/author/podcaster definitely wasn’t on my radar of career choices.
I think the question of what you want to be when you grow up is kind of a stressful one, and we’re trained to answer it as if a job is the only right answer.
How about happy, excited, or interesting?
36. “Simplicity is the ultimate sophistication.”
I love this quote from Leonardo da Vinci. I have a habit of making things more complicated than they need to be, and this lesson often helps rein me in.
With most big decisions or projects, I try and ask if this will ultimately make life simpler or more complex? And if it adds a layer of complexity, is it worth it?
Simplify, simplify, simplify.
37. Happiness = Meaningful Work + Meaningful Relationships + Sense of Progress
Good things happen when you’re working on something you care about, you feel like you’re getting better either at that work or in other areas of your life, and you have someone to share with.
I won’t get too philosophical here, but if you’re unhappy, I think it’s likely that one or more elements of that equation is missing.
38. If you want to be more disciplined, be more disciplined.
I think this line came from Jocko Willink, and maybe the context was people were asking for tricks and hacks to get up earlier or stick with their fitness routine. His response? There’s no secret weapon: just be more disciplined.
And what I’ve found is that the more you practice it, the more you do it. You start to build that identity habit.
39. If you’ve already won the game, why take additional risk?
This was a line that stood out to me from Ramit Sethi’s book I Will Teach You to Be Rich.
He was talking about it in the context of bond investing, but I interpreted it more broadly. If you already have everything you need, it’s OK to “miss out” on the pursuit of more.
40. Luxury is feeling unrushed.
This is a Tim Ferriss quote, that has especially resonated over the last couple years.
We’re no longer rushing to get kids out the door, to get Bryn off to work, and it’s so much more relaxed. My work days start a lot later — and I recognize and appreciate that as a luxury.
Luxury doesn’t mean designer brands and fancy cars and houses; it’s time freedom and being able to allocate and invest that time how you like.
It’s being in charge of your own calendar and agenda instead of reacting to someone else’s. Think about what you’re optimizing for.
41. And a bonus: people love bonuses.
Under-promise and over-deliver.
Apologies to Kevin Kelly!
- Freshbooks.com – Start your 30-day free trial today!
- Hulu Ad Manager — Make the move to streaming TV advertising today and reach a highly engaged audience for as little as $500 per campaign!
- Blinkist – Start your free trial or get 3 months off an annual plan and get instant access to 3000+ bestselling book summaries.
Looking for More Side Hustle Help?
- Start Your Free $500 Challenge. My free 5-day email course shows you how to add $500 to your bottom line.
- Join the free Side Hustle Nation Community. The free Facebook group is the best place to connect with other side hustlers and get your questions answered.
- Download The Side Hustle Show. My free podcast shares how to make extra money with actionable weekly episodes.
Any favorites from this list? What would you add?
I asked Side Hustle Nation for their input and came up with this compilation of words to live by from their responses.
Let me know in the comments below.