28 Important Lessons on Money, Life and Business (2024)

Here are a handful of lessons from 2018 (although many of these ideas originated during a lifetime preceding that). I’ve shared most, but not all, of these lessons on Instagram in the past year.

1: Your net worth is not your self worth. That’s true regardless of whether your net worth is low or high. Money is what we accumulate, but it’s not who we are.

2: It’s inefficient to worry about the small stuff (like how much you’re spending on avocado toast) if you’re not taking care of the big stuff (like how much you’re spending on your home, car and food, especially restaurants.)

Don’t patch a few minor ceiling leaks if a huge section of your roof is missing.

3: Don’t make decisions based on money alone. This applies to both earning andspending. For example:

Don’t choose a college major or a career just because you think it will be high-paying. You’re more likely to fail (or languish in mediocrity) if you’re not passionate about your work. You’ll earn less over your lifetime, because you won’t advance. You’re more likely to make a midlife career change, which comes with its own costs, both direct (tuition, unemployment) and indirect (years wasted through suboptimal work).

Making the “financially rational” choice is expensive and irrational, because it’s unsustainable.

Likewise, don’t accept a job or internship just because you think it will look good on a resume. Take it if you’re excited about it. One of the best decisions of my life was turning down a job offer that everyone around me exclaimed would “look good” and “be a great stepping stone.”

Here’s a litmus test: If you were prohibited from listing this job on your resume, would you still accept it?

This principle stretches beyond career choices. For example:

• Don’t move to a city, town or country only because the cost-of-living is cheap (and for no other reason beyond that).
• Don’t stay in a relationship just because moving out and restarting your life is going to be expensive.
• Don’t buy a home that you dislike, just because it’s cheap.
• Don’t eat a diet of crap-on-crap, just because it’s cheaper than veggies.

You’re optimizing for living a sustainable, healthy, whole life, not for improving your net worth. Any savings or investment gains that come from neglecting the bigger picture, and making choices from a space of Spock-like rationality, are likely to erase themselves when your heart catches up with your mind.

If your heart’s not in it, it’s not going to work out. And that will ultimately cost more in the long-term, both financially and through the way it wears down your spirit.

Money that comes at the cost of YOU is too expensive.

4: If you have to talk yourself into something, your heart’s not in it.

Here’s an effective litmus test: when other people ask you “Why did you choose [X]?,” do you get triggered by the question? Do you rush to defend your choice? If so, then you might be trying to persuade yourself.

5: Your blind spots are bigger than you realize.

When you look back, they’ll be obvious. But no matter how hard you try to manage and optimize everything, you ARE overlooking something big. You’re doing it now. We all are. Stay humble, don’t make assumptions about other people’s motivations or future behaviors, and protect your downside.

6: Your foresight is wiser than you realize.

You’re setting up your Future Self for amazing things, and you’re doing it in ways that you don’t even realize. Despite all of your planning and best efforts, Future You will look back on today and say, “I’m really glad I did that” about decisions that, at this moment, you find casual or inconsequential. No matter how hard we try to plan for the future, some of our best decisions are made by intuition or accident.

7: Most people won’t understand. And you don’t need their approval, even if they’re your boss or your family. (Excuse me, I meant “especially if.”) If you’re living inside of your integrity, and other people don’t like it, that’s not your problem.

8: You can delay gratification, but you can’t defer happiness. Or at least, you shouldn’t.

It’s tempting to think that you’ll be happy later — after you start earning more, after you quit your job, after you can live on your passive investment income. But happiness can’t be deferred.

Don’t over-fixate on the future. Sure, goals are great, but if you’re too goal-oriented, you risk missing the present moment. You live for the next milestone.

Plan for the future, don’t live in it.

9: We don’t buy things. We buy stories.

We don’t (just) buy clothes. We buy the story and identity that the clothes represent. We buy the story that we’re professional, or modern, or hippie, or grunge.

We don’t (just) buy food. We buy the story and identity that the food represents. We buy the story that we’re clean and healthy, or a gourmand, or an animal-loving ethical eater, or a proud junk food addict.

We don’t (just) buy makeup. We buy the story and the feeling that we’re beautiful.

We don’t (just) buy transportation. We buy the story that we’re eco-friendly, or frugal, or rich and luxurious.

Every time we make a purchase, we’re buying a story, identity and feeling. The next time you’re thinking about buying something, ask yourself: “Do I really want this thing? Or do I want the story that it tells me about myself?” Then ask, “Can I get that story without buying this item?”

10: Self-care IS business care.

The time that you spend going to the gym, practicing yoga, writing in your journal, or connecting with a close friend on the phone is not time that you are spending away from work or hustling.

Self-care is part of your work. It sustains your hustle. Even laptops need to recharge.

11: Take care of the present, and the future will take care of itself.

This means:

• Exercise. Eat clean. Sleep. Hydrate. Wear sunblock.
• Save for emergencies.
• Max out your retirement accounts.
• Slowly add to your investment portfolio (for example, buy one rental property every two years.)
• Start a side business.
• Volunteer and/or donate to worthy causes.
• Spend quality time with family and friends.

Get aligned and right with today, and tomorrow will take care of itself.

12: Don’t defer happiness. Discover happiness.

Sure, I could buy a BMW, but I wouldn’t enjoy it. It’s not me. I’m not “making a sacrifice” by driving an older, used car. I prefer used cars.

Don’t defer happiness. Discoverhappiness within the healthy, optimal choice.

13: Forget about results. The goal should be the action itself.

Instead of: “My goal is to lose two pounds per month.”
Try: “My goal is to fill up on vegetables, avoid processed sugars, and lift weights every-other-day.”

If your goal is based on results (lose X pounds), you’ll experience a demoralizing lag time between ‘actions’ and ‘results.’ But if your goal is based on the action itself, the actions ARE the results: “I roasted veggies, success!” or “I lifted today!”

Instead of: “My goal is to start a side business that earns $3,000 per month.”
Try: “My goal is to work on my side hustle from 7 pm to 10 pm every weekday.”

If you focus on actions, rather than results, then you’ll reduce your fear of failure and the procrastination that it creates. The fear of failure is terrifying, in part, because it’s a fear of something that’s outside of your control. You can’t control the outcome, you can only control your efforts. So let go of the outcome. Focus on the efforts. Let the consequences unfold as they may.

14: It’s not about what you want. It’s about what you’re willing to sacrifice.

I want six-pack abs. But I’m not willing to make the sacrifices that are necessary to create them.

It’s easy to list goals, aspirations and wants. But that’s not telling. The more prescient question is, what pain are you willing to endure? What sacrifices are you willing to make? What trade-offs will you embrace?

My friend Sheila (not her real name) is self-employed and holds $50,000 in credit card debt. She says she wants to pay it off. And sure, I believe that she wantsthat.

But she spends on frivolous items. She bought a monthly package at a salon, where she gets regular waxing and pedicures, because “it was a good deal!” She’s leasing a brand-new vehicle. ⠀

Although she’s self-employed, she’s not trying to find more clients. She works 4-5 hours a day. She earns enough to pay her bills and make the minimum payments on her credit card, but no more.

She hasn’t made a dent in repaying her debt, other than the minimum payments, over the past year.

I’m not surprised.

I believe she wants to repay her debt. Who wouldn’t? But she doesn’t want to accept the trade-offs. She’s not willing to work more than 4-5 hours per day, or sacrifice her spa retreats, or downgrade her vehicle.

Duh, of course she’s not making progress.

The question isn’t “what do you want?”
The question is, “what trade-offs are you willing to make?”

15: Stop telling young people to “enjoy it now while you still can!”

My friend Kim and I traveled to Europe together 10 years ago. At the time, I was afraid this would be our last trip.

I was afraid that after our Europe excursion, we would return to the workforce and get stuck in 9-to-5 jobs that would limit us to two or three weeks of vacation per year.

I was afraid we would trade our freedom for mortgages, cars, basem*nts full of stuff.

Ten years ago, the “adults” told us to enjoy traveling now, while we still could. Their implication was that once we reached our late 20s or 30s, this window would be closed. We would succumb to mortgages and jobs and restrictions.

“Enjoy it now while you still can!,” they said.

Fortunately, they were wrong.

I built passive income through real estate investing. And Kim saves 50 percent of her income as a firefighter for the City of Austin, which gives her the flexibility to quit her job. She’s not financially free yet, but she has plenty of runway.

This is the power of managing your money, rather than letting it manage you.

We’re not unusual, either. Across the blogosphere, there are thousands of examples of people who travel full-time with children, dogs, or while managing illnesses and obstacles. Some people work the gig life, others are financially independent, others are laptop entrepreneurs. Some are all of the above.

Some travelers are roadschooling their children, turning their life into the ultimate field trip. Some are creating new businesses from coworking spaces in Thailand and Colombia. Some travel for one year, others for a lifetime.

There’s a difference between “I can’t” vs. “It’s not a priority,” and the adults who advised us a decade ago that we “couldn’t” travel and explore when we were older must have missed this basic fact. Adventure may not have been a priority for them, which is fine, but they were remiss in advising young people that their lack of priority translates to someone elses’ inability.

The phrase “enjoy it now while you still can!” implies a bleak, boring future. (Ditto for the phrase “your college years are the best years of your life.” Really? Do the next 60 years of your life suck that much? That’s awful!)

Let’s drop that idea. The future can be brighter than the past, and each of us has the power to make it so.

16: You succeed at the level of your preparation.

To quote James Clear: “You do not rise to the level of your goals. You fall to the level of your habits.”

17: Beware of pleasure at the expense of happiness.

Imagine that you have a giant bar of milk chocolate. You eat the entire thing in one sitting. That’s pleasure. But it won’t bring you enduring happiness.

Happiness is long-term. Pleasure is short-term. Don’t trade dollars for pennies.

18: Happiness comes from making progress.

Not from drinking mai tais on the beach. Not from fancy cars. Not from buckets of ice cream. Happiness comes from spending a day making progress at something you find meaningful.

I have a friend who teases me about working so much. She’ll text me at 9 pm on a Monday to say, “Hey, I’m in your neighborhood! Come get a drink!” and I’m like, “It’s 9 pm on a Monday!”

She’s also self-employed, and never fails to point out that I don’t actually have to work the next day. Which is true. Then she points out that I don’t need the money. Also true. Then she questions why I’m being such a square, and applauds herself for having escaped the rat race. Which is false; she’s in $75,000 of credit card debt and unprepared for retirement. But anyway.

Here are two things she doesn’t understand: (1) I find more happiness in working and progressing than I do in sitting on a bar stool on a Monday night, and (2) I’m prioritizing anything productive, which could include reading a book, watching an educational video, changing out the reverse osmosis filter under my kitchen sink, making fresh pesto from scratch, building a Spotify playlist for my next workout, or organizing a huge stack of mail.

Productivity and progress — in any arena of life, not just income-production — is a true source of meaning and happiness. Yes, socializing is important and soul-nourishing, but that doesn’t mean I need to say yes to every invitation or go out on Monday nights (or, for that matter, on Friday nights). Human connection is valuable, but if an activity is no longer meaningful, it loses its value.

19: Waste is the opposite of value.

20: Business and financial health is a reflection — a consequence — of overall health, especially brain health. Everything starts with a healthy brain and mind. This is the foundation for all success, both physical and financial.

21: The concept of “delayed gratification” applies to both spending and earning. Most people only know this concept in the context of spending. They associate ‘delayed gratification’ with deferring a consumer purchase. But delayed gratification, when applied to the income side of the equation, is also the concept behind entrepreneurship, investing and building passive income.

(That said, I’m not delaying jack. I find entrepreneurship and investing to be inherently gratifying.)

22: Live at the boundary of your comfort zone.

If you’re too nestled inside of your comfort zone, you won’t push yourself to the edges of your limits; you’ll limit your progress. And if you’re too far outside of your comfort zone, your life will be a pit of anxiety and worry and stress until you take a hard pendulum-swing firmly back inside.

Living at the edge of your comfort zone might mean cutting expenses until you’re living just a little bit more frugally than you’re comfortable with.

• • It might mean waking up earlier than you would prefer to work on your side hustle.
  • It might mean overcoming the fear of meeting people at events, investing in training and education, raising your freelance prices, or asking for a raise.
  • It might mean quitting your job when the time is right, even though that makes you nervous.
  • It might mean traveling to a foreign country, including solo travel.

It might mean all of the above. Or it might mean something different entirely.

23: Focus on value, not cost.

A decade ago, I dismissed small indulgences, like flowers or candles, as a waste of money. I saw these as spending drains. These days, I look at value rather than cost. Does this make me smile? Does it brighten my day?

I’ll calculate how many hours of my life might have gone into that purchase, and ask myself if it’s worthwhile. And many times, the answer is yes, it absolutely is.

I’m willing to work an extra hour — or if we’re using a FIRE formula, I’ll work an extra year — if it means that I can still enjoy X, Y and Z. That’s absolutely worthwhile.

There’s a great quote from Oscar Wilde in which he says that “a cynic is a man who knows the price of everything but the value of nothing.”

Don’t let frugality turn into cynicism. Value matters more than cost.

24: One of my best friends wrote me a letter earlier this year and asked me these four questions:

a: What do you have (skills, capabilities, possessions) that might someday change or be gone? Take a moment to appreciate them, and accept that they will eventually end.

b: What acts of kindness have you done that you are most proud of? Take a moment to experience the joy that comes from these memories.

c: What experiences have you had that you cherish? These are yours no matter what, and can never be taken from you.

d: Who are the most important people in your life? How recently have you told them?

The answers to these questions reveal more about your life than any spreadsheet, any tax-optimization strategy, any investment debate ever could. This is life. The rest is noise.

25: Learning how to learn, thinking about how to think, and deciding how to decide, are the most important skills of all. (It’s also the secret mission of this blog and podcast — to teach people, including myself, how to improve the skill of thinking.)

26: “Calling something ‘work’ does not make it a more noble use of time than anything else. Work that doesn’t advance you toward the life you want is still wasted time. You will never get those hours back, and we only get so many.”

This is a quote from Laura Vanderkam (a two-time podcast guest), and it summarizes a huge piece of my life philosophy.

But just as calling something “work” doesn’t necessarily make it more noble, calling something “leisure” doesn’t necessarily make it superior OR inferior to work. There’s meaningful leisure, and then there’s wasting time. Look within yourself to know the difference.

27: Life teaches you the same lessons, over and over, until you learn them.

28: We give the advice that we most need to hear. Everything that I’m saying, I’m telling you because I need the reminder myself.

While you’re here, I’d like to share my 2018 Year in Review.

At the start of 2018, my goals included:

• Don’t travel as much (I’m feeling exhausted from years spent in airports and on highways). Enjoy home and build community locally.
• Workout and build lean muscle mass.
• Launch the rental property course.
• Develop stronger relationships with friends.
• Grow the podcast.
• Raise at least $12,000 for charity: water.
• Deliver an awesome keynote speech at the World Domination Summit.

(Yes, I know … goals are more effective when they’re focused on actions, not results. Yet the results pop into my brain nonetheless. Sorry not sorry.)

How did I do?

Goal: Don’t travel as much.
Verdict: Meh. Moderate success.

Last year I traveled to 4 countries and 7 states, which is what I’d consider to be a lower-travel year. (Because I’m a nerd, I made a spreadsheet to track it.)

My greatest success within this goal was that I managed to stay home for 60 consecutive days — the entire months of February and March 2018. This marked the first time EVER I’ve stayed home for 60 consecutive days since moving to Las Vegas nearly four years ago.

I’d consider this to be a moderate success.

Upcoming 2019 is thick with travel plans. I won’t even have 30 consecutive days at home. This year is going to involve an immense amount of life on the road. I’m glad that I slowed down in 2018, however moderately, to give me the energy to rest and prepare for an on-the-go 2019.

Here are my 2019 travel plans, as of now (and subject to change):

January – Los Angeles, Denver, Winter Park
February – Austin
March – Austin
April – Austin
May – Seattle
June – Chile (and maybe Argentina)
July – Colorado Springs
August – either Burning Man or Europe or Japan
September – Washington DC
October – Joshua Tree, San Diego
November – Ecuador
December – San Diego

(By the way, here’s how I fly for free.)

Goal: Workout and build lean muscle mass.
Verdict: Hahahahahahahaha.

Goal: Launch the rental property course.
Verdict: In September, we launched to a second round of Beta Testers, in a group that we call “Beta Plus.” These students, around 190 in total, went through the course in (mostly) sequential order, offering feedback along the way.

We’ve created a Knowledge Base, a Known Issues Document and a list of Additional Improvements based on their feedback, and we’re continuing to update the course.

We also hired a designer and a developer to custom-build the platform, which we launched to the beta-testers in November. Check it out:

We’re eyeing a full (non-beta) launch sometime-in-early-2019, I hope. If you’d like to learn more, join the free VIP List. You’ll also get a free email series on rental property investing for beginners.

Goal: Develop stronger relationships with friends.
Verdict: Success! I nailed this one in 2018, devoting a lot more time and energy to connecting with friends who live across the country.

Goal: Grow the podcast.
Verdict: Success! We started the year with 2 million downloads and ended the year just shy of 5 million downloads (4.6 million). We’re averaging around 250,000 downloads every month, as a weekly show. (The Suze Orman episode aired in October, and we received 315,000 downloads that month.)

More importantly, the podcast community is engaged. They’re active in our Facebook group, they’re involved on Instagram, they leave reviews on Apple Podcasts (more than 1,166 reviews to date!), and they support our charitable drive. Which leads to the next point …

Goal: Raise at least $12,000 for charity: water.
Verdict: Success! I’ll let this image speak for itself:

Thank you thank you thank you thank you to everyone who donated to the campaign or bought a t-shirt. We’ve raised enough money to sponsor a water project (or two?!), and around 732 people will be able to drink clean, safe water.

Goal: Deliver an awesome speech at the World Domination Summit.
Verdict: You be the judge. 🙂

In 2012, I tried to buy a ticket to the World Domination Summit, but the tickets were sold out. I couldn’t get there as an attendee.

Fast-forward to 2018, and I’m delivering a main stage keynote. That’s how transformative six years can be.

Because of this history, I felt determined to deliver an amazing speech. But I knew I wouldn’t be able to focus on practicing my speech at home, amid endless distractions.

In order to rehearse this speech, I drove to Yosemite National Park, slept in the back of my car, and every night, I lit a campfire and rehearsed the speech to the flames. It gave me the quiet and solitude that I needed to focus on delivering an incredible performance on that stage.

I slept in my car for eight nights to rehearse this speech.

This speech is one of the highlights of not just 2018, but of my seven-year history as a blogger. If you haven’t watched it yet, I encourage you to do so. I promise it’s worth 25 minutes of your life.

If you’d rather listen to audio, here’s the podcast episode in which I shared this speech.

Other highlights from 2018 included:

1: Winning the Podcast of the Year Award at the Plutus Awards, held at the financial blogger conference, FinCon.

2: Winning the Lifetime Achievement Award at that same conference (although I still don’t understand — how do you win “lifetime achievement” at 34? Also, I’m not dead yet.)

3: Watching the craziness of the Suze Orman interview going ultra-viral, and seeing the interview get written about on Time.com, Marketwatch and many other websites.

4: Discovering that people view me as “calm” in my handling of Suze. (Cool! Although I wasn’t trying to be calm … I was coming from a space of genuine curiosity. I guess that has the same effect?)

5: Getting featured in a two-page spread in Money Magazine.

6: This.

7: Hearing from hundreds of readers and listeners who paid off debt, bought a rental property, reached a six-figure or seven-figure net worth, or accomplished anything that was amazing and meaningful in their lives.

They wrote or tweeted or commented or left a voicemail to say thank you, even though the credit belongs to them.

I can be a catalyst, but I cannot take action for you. Only you can do that. Many of you did, and you reached out and told me about it. Reading or hearing those voice messages brought me a lot of joy throughout the year.

So. Whew. That was 2018. It was an amazing year for Afford Anything, even though it was a tough year personally. This community has been my rock, support and source of meaning and joy. I’m excited to keep building on this in 2019, to spread the philosophy and ideas that this platform represents.

Cheers to you. And Happy New Years 2019.