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30 Lessons from 30 Years

Let’s not pretend like I have life all figured out. None of us do. We’re all experimenting and figuring things out as we go.

Despite that, I feel I’ve built a pretty cool life I’m really happy with. And the thirty lessons in this post are all things that have contributed to building that life.

I’m not an expert in any particular area and while it’s tempting to call myself a jack of all trades, I’m closer to a master of none. So don’t take my thirty lessons as rules but merely suggestions. Hopefully you’ll find one or two that help you build a pretty cool life as well.

Life & Relationships

You’ll find the thirty lessons grouped in categories of Life & Relationships, Business & Career Development, Happiness, Health, Personal Finance, and Bold Calls. I wanted to go with a random assortment, but Vanessa suggested I organize them. Which is a solid bonus lesson to stat with—listen to your wife.

Don’t give advice until someone asks, preferably twice. 

Have you ever seen how passionate women in fitness are about men not critiquing their form or physique? Yeah, pretend that applies to everything for everyone.

Nobody wants to be critiqued. You’re never going to make any friends giving out unsolicited advice, and it’s not like the person you’re giving said advice to will even use it. Keep your criticism to yourself, almost always.

Says the guy criticizing you for criticizing others.

Friends matter, even for lone wolves like us.

I’ve gone through several phases of friendship in my adult life. In some phases I was surrounded by lots of friends and roommates, while in others I was more isolated. Can you guess which phases I have more positive memories from?

Being alone is a skill I developed early on in life thanks to growing up as an only child in a rural town. And thanks to the internet, we can all maintain friendships from isolation. It’s never been easier to trick yourself into thinking you have friends without ever actually hanging out with them.

For example, there’s a guy I consider a good friend. I was even in his wedding in May of 2015, and he recently came to our wedding in October of 2020. Other than bumping into each other at the gym a few times, those were the last two times we saw each other (entirely my fault).

This is why one of my primary objectives for my thirties will be to create and develop friendships. It’s not something that comes natural to me. So I’m planning to get out of my comfort zone by initiating more gnarly bro hangs, hosting things at our house, and potentially turning off my phone’s do not disturb setting.

It might sound odd, but I’m treating it like an investment by putting a large portion of time and money into this area of my life. We’ll see if anyone likes me!

Know a little about a lot. 

I realized the importance of this early on thanks to my time as a personal trainer. Maintaining good conversation with a variety of clients for 20-30 hours per week took serious broadening of interest areas.

It’s much easier to relate to people with a little common ground, and we all like talking about things we know a lot about. So by knowing a little and opening the door for people to tell you more about their area of expertise, they talk to you more. And when they talk to you more, they get comfortable and tend to like you more.

Ask more questions. 

Even if you don’t know a little about a lot yet, everyone can ask more questions. While there may be some technique to asking great questions, you can get a long way with mediocre lines of questioning. It takes a little practice, and genuine curiosity helps, but you can almost always dig deeper into every conversation piece.

Aim to keep questions open ended and avoid controversial topics when getting to know someone. I’ve always found areas like TV shows and movies, books, careers and schooling, sports, and video games (mainly for the fellas) to be safe spaces where you can successfully get people talking.

I’m no interrogation expert so if you need more help in this area, the Harvard Business Review has a great article on asking better questions.

Get married. It’s the best. 

Okay, I’ve only been married for, like, a month at this point. So I won’t pretend to be an expert on marriage. I guess a better heading might be “find a great partner” or something along those lines. But seriously, the past five years with Vanessa have been the best

And I’m not only talking about the lovey-dovey stuff. She was a huge supporter in me quitting my job to pursue this pipe dream of blogging and online business. I never had distractions of dating or pressures from a new partner about working too much. Vanessa understood me, helped me, and I wouldn’t have been able to build the business I have without her.

I’ve seen advice out there for young entrepreneurs to avoid finding a partner so they can focus solely on their entrepreneurial endeavors. While it may work for some, I can only imagine the egocentric nutcase I would have become over the past five years without Vanessa.

Find common interests with your partner.

Even if you have to fake it.

Some of my fondest memories with Vanessa are when we’ve shared experiences and conversation around a common interest. Some examples:

  • Game of Thrones, The Witcher, Star Wars (I fake it)
  • Standup comedy
  • Food
  • Women’s fashion (I faked it in the beginning but have gotten genuinely interested at this point)

Some examples of things one of us into, but the other hasn’t gotten on board with (maybe one day):

  • Breaking Bad (my favorite show of all time)
  • The Wheel of Time (Vanessa’s favorite book series)
  • Music
  • Travel content (I’m warming up to it)

We certainly have our own interests the other will never share, and that’s totally normal. I’m just saying it’s worth making an effort to find or create some common ground with your partner. Keep an open mind (an important lesson on its own) and give The Bachelorette a shot (just kidding we hate those shows).

Business & Career Development

I’m passionate about work and could probably give you thirty lessons in this category alone. If you relate, you’ll want to keep an eye on our online business category.

Focus is a superpower in 2020. 

While everybody else is scrolling social media, playing Fortnite, or working their way through the entire Netflix catalog, you can get ahead with a little focus. Whether you lock your phone in another room, use browser blockers, or use work-relax timers—learning how to avoid distractions and get to work is a skill in major demand.

Bonus points if you can get it done without stimulants.

If you need some extra help, James Clear has a great article on how to focus.

Be bold. 

Nobody cares if you fail. Take risks and do the things you’ve always wanted to do. What’s the worst that could happen?

Twitter is underrated.

Seems like a perfect time to mention the bird. I’ve curated a group of people to follow on Twitter that have seriously leveled up my knowledge in areas like business, marketing, personal finance, and investing. This education has been completely free, and there’s no telling how much money I’ve made from things I’ve learned.

My ROI from Twitter might be (is) higher than any other education I’ve paid for.

To start curating your own follow list, start with a few people you trust and respect or would like to emulate. Then look at the people they follow and engage with. This is a slow process. I’ve been working on my group for 3-4 years and follow less than 75 people. I’d argue the smaller the better when you’re first starting.

Are you learning or procrastinating?

Speaking of reading one book a week, if you’re doing it purely for enjoyment, that’s a fine idea. If you’re reading a non-fiction book every week with hopes of bettering yourself, however, you might be procrastinating.

Reading self-development or business books without eventually putting the information to work is a waste of time. Make sure you’re implementing the things you’re reading about if that’s the goal.

I’m a fan of “just in time learning” when it comes to business. While building our blogs, I’ve learned all kinds of things about web development and design, SEO, and marketing. Some of it I read in books before starting, but I learned most on the fly as needed. This is way more efficient than hoarding knowledge you may never need.

Everyone should go from consumer to creator.

We all spend so much time online, collecting information and consuming content. You may not feel creative or like you have anything worthwhile to say, but I bet you do. There are people creating content about topics that most would consider obscure or weird. And they’re not only creating, they’re crushing it.

If you’d like to see some examples, check out Starter Story. We’ve even shared our story on their site!

I think everyone should start a blog or personal site. You can write about anything that interests you and share the things you’re doing and learning. There’s no telling what it could turn into or who could read it and want to connect with you. For a quick guide on starting your own site, check out our post on starting a blog.

Be prolific when you’re young.

I read this somewhere in my early twenties and thought it would be a long time before I had any issues, but I’m already feeling this at 30. While I’m speaking more to creators and artists, putting in quality work while you’re physically capable and unburdened with responsibility is a universal lesson.

Take advantage of the beginning of your career and put in the work while you’re able, excited, and free. It’ll make life easier down the road.

Specific knowledge and experience pay.

Remember when I said knowing a little about a lot was important? Well so is knowing a lot about a little, especially when it comes to the dollar dollar bills.

Over the course of your life you’ll develop, similar to Liam Neeson, a certain set of skills. Combining that set of skills and expertise makes you uniquely and highly employable. And thanks to the internet, your career options is becoming exponentially bigger every year.

This is all a complicated way of saying you have (or will have) a one-of-a-kind offering to the world. You should leverage that offering for a beaucoup of bucks.

If you’d like to read more about specific knowledge, check out this article on Naval Ravikant’s specific knowledge.


After all, isn’t that what it all boils down to at the end of the day?

Maximize the good days.

You know those days I’m talking about. The ones where you wake up early with a smile on your face, are super focused and get all your work done, make it to the gym, and just crush it at life in general.

I’ve found that focusing on getting the most out of the good days is way more productive than trying to fix the bad days. On the days where you’re having a great workout, for example, stick around and pump out an extra 15 minutes. Or if you’re in the zone with your work, clear your schedule and get things done. That way, when the bad days come, it’s much easier to feel good about mailing it in and hitting the reset button for the next day.

Also, don’t waste your good days watching TV or doing things you can do on bad days (unless you want to).

The internet is not always a good representation of the real world. 

It’s easy to think the world is ending if you’re looking at your phone or watching the news all day every day. Sure, some things are bad. But overall there’s never been a better time to be alive. There’s so much good in the world if you know where to look.

The goal post always moves so start enjoying things more. 

When I left my “career” in 2017 to make something happen with blogging and online business, I had the goal to replace my income. I remember thinking if I could do that while working on something I cared about, I’d be happy.

And when I replaced my income about a year later, I felt no different and decided I probably needed to double my previous income.

About a year later, I reached a similar milestone and extended the goal post yet again.

Now my income is 4-5x what it was at my previous job. And while I am extremely happy with my life and work, it doesn’t feel all that different.

Living in the now instead of the future is a constant struggle. I’m clearly still working on it myself but here are a few things I’ve found helpful:

Getting busy.

No, not that kind of busy. Though I guess that works, too. I mean shifting my focus from what might happen to making things happen.

Also, working on things that matter to me with people I want to work with.

Practicing gratitude.

Gratitude is becoming a woo woo term, but it’s so easy to lose sight of how good things are. It’s not always easy but taking a step back to count your blessings always helps.

Celebrating success.

We’ve done a better job at celebrating successes this year. Things like hitting 1M page views in one month on, revenue milestones, social media growth, and collaborations with others have all been acknowledged and briefly celebrated. Bringing Vanessa on board to work with me full time was a huge milestone from this year.

Moving to a major city was a good move. 

We moved from Little Rock, Arkansas to Austin, Texas in July of 2019 after a year or two of researching places to move. Other potential cities included Nashville, Denver and Boulder, Kansas City, and a few other places in the Southeast. We wanted a place with more young professionals and like-minded people, opportunities for work and collaboration, things to do, and better weather.

After visiting cities on our list, Austin felt like the perfect blend of back home and something new. We decided after one weekend here it was the right spot for us.

Since moving, we’ve had a blast (even through a pandemic) in Austin. The food scene is even better than advertised, and we’ve made a great group of friends. I feel that environment is a major factor in the happiness equation, and changing our environment was a giant boost for us both.

Austin aside, moving in and of itself was a welcomed growth opportunity. Moving to a new state without any family or friends was challenging. We had to get to know the city, take care of all the annoying details like drivers licenses, make new friends, finding a new vet and doctors, and everything else that comes with moving. Vanessa and I really bonded throughout the entire process and embraced getting out of our comfort zones together.

10/10 recommend.

But water your grass. 

We still have the occasional conversation about potential destinations, especially during the peak summer months here in Texas. But we also realize that the perfect place doesn’t exist.

Want cooler weather in the summer? Cool, you’re probably getting snow in the winter.

The Pacific Northwest is absolutely beautiful. It’s also cloudy and/or rainy for something like 200+ days out of the year.

And good luck getting high speed internet on your Montana dude ranch.

At some point, it’s helpful to just commit and focus on “putting down roots” somewhere. Whether that’s finding a group of friends, starting a family, or getting involved in your community, there’s likely more joy to be found near you than in some unknown place with greener pastures.

Time flies and things happen fast.

You can change your life in a year. Maybe even less than that. Starting something new can be daunting but think about how much can happen in a year.

  • You could lose 50+ pounds in a year.
  • I’ve never seen one of her Tik Tok’s, but Charli D’amelio gained something like 100M followers in a year. More realistically, you could get your first 10,000 Instagram followers or 1,000 email subscribers.
  • You could read 52 books (one book per week).
  • Like I mentioned above, you could replace your current income with your side hustle and make that your full time hustle.

Do more. Make something happen.

Get a dog.  

I was never a pet person before Vanessa snuck Sir John into my life. Now I don’t know what I’d do without him. He’s an integral part of every day and I’ve spent more time with him in the past five years than anyone.

Getting a dog may mean having an extra expense, a messy house, and sacrificing travel, but it’s so worth it.

It’s okay to not want to travel.

Speaking of sacrificing travel, Sir John’s been a solid excuse for me staying back on Vanessa’s three European tours. Caretaker duties aside, I’m not much for travel, especially international travel. I used to think it was weird that I had no desire to travel the world, but it turned out I just enjoy other types of experiences.

Instead of airplanes, trains, and foreign landscapes, I enjoy eating at new restaurants and visiting cities in my own neck of the woods.

Am I missing out on culture and building a more worldly sense of things? Maybe. But it’s what I like, and I’ve realized theres no need to feel bad about doing things you like.

Stop doing things you don’t want to do. 

Likewise, it’s okay to say no to things. Set boundaries with people and stick to them. It takes some time, but they’ll eventually understand. And if they don’t, that’s okay, too.


I’ve realized that similar to happiness, health is everything. Don’t let the length of this section convince you otherwise. Cherish your health while you have it, don’t take it for granted, and make it a priority from an early age.

Go for more walks. 

It’s good for your body, your mind, and your relationships if you can walk with others. And if you can’t walk with others, figure out how you can.

Wear sunscreen, stop drinking so much caffeine, put your phone down more, and go to bed. 

Since you’re going for more walks, you’ll need protection from that giant thermonuclear bomb in the sky. I wish I’d taken better care of my skin when I was younger (and I’m only 30).

I also wish I would’ve delayed my excessive caffeine consumption. I certainly had enough energy to get through my twenties without it. I’ve always known my caffeine intake was a problem, but it wasn’t until I started paying attention to my blood pressure I realized how jacked up I really was. This is worth paying attention to because, again, I’m only 30!

If you have trouble sleeping, you need to fix it ASAP. Sleep is boring but huge when it comes to your health. Cutting back on caffeine could be an option, as could putting down your phone before bed. And while you’re at it, just put your phone down more often period.

Don’t stop moving.

Protect your fitness regimen at all costs. If you’re currently fit and active, aim to never stop moving. I’m convinced going from super fit to kinda fit leads to pains and aches that make it tempting to go from kinda fit to not-so-fit.

Personal Finance

I am not a finance professional. These are my opinions and possibly bad advice. I’ll say the same thing I say about fitness advice. What works for me probably won’t work for you, but I bet you can take a thing or two away from this to better your situation.

Don’t pay off your student loans. 

And I’m not saying hold out until the bailout that’s never coming wipes away your debt. I’m saying make your minimum payments and either invest the remaining money or use that capital to fund a business if you’re feeling froggy.

Instead of paying off my remaining $10,000 in student loans in 2014, I made my $100/month payments and invested the rest. If you look at a graph of the market since then, you can see that money did well. But I wasn’t along for the full ride. Instead, I cashed out investments in 2017 to give myself a 6-month runway to start a business. My frogginess paid off.

This only makes sense for some. If you have a beaucoup of student debt or a high interest rate on your student loans, you’ll want to make larger payments on those. You won’t be able to out-earn the interest you’re accruing.

It’d also be a good idea to have an emergency fund or at least three months worth of cash on hand before you start investing or funding said business. Basically, if you’re barely getting by making your minimum student loan payments, this may not be the move for you.

Save that money. 

Money doesn’t buy happiness. It does buy freedom.

If you want to take risks in your career, reduce your stress later in life, and open up doors for future you, start saving. Building a habit of saving will also teach you how to live within your means and limit lifestyle bloat.

The less money you need to live on, the less money you need to make. And the less money you need to make, the more freedom you have.

Maybe skip the house. Definitely skip the new car. 

Speaking of freedom, I can’t think of a bigger trap than the super young home owner. I’m not sure where I stand on the rent vs buy argument. Though I can say with certainty the flexibility and liquid assets renting provides is extremely valuable in my eyes.

If you know you’re staying put in your city, have a big chunk of money for a down payment, and are buying a home within your budget, I’ll never fault you for that.

If you’re buying a brand new car straight off the lot, on the other hand, I’ll just say yikes.

Credit cards are useful tools for those responsible enough to wield them.

My first foray into credit was out of necessity, not strategy. I was a poor college student in need of some extra spending power in between jobs. I had no existing credit so it took a few attempts to get approved, but Capital One eventually gave me a card with a $750 limit and a $20 annual fee, which I still pay for every year (age of credit history is important).

Since then, I’ve been approved for 20+ credit cards and get a new card, on average, every six months or so. Why so many? Sign up bonuses. Each card after the initial Capital One card has netted me between $150-$400 in sign up bonuses. I pay for nearly everything in my life with a credit card and pay them off in full every month, never accruing any interest.

Since I don’t own a home or have a car payment, credit cards are the only thing I’ve used to build credit. And as of this writing, my credit score is in the 800s. Used responsibly, credit cards are one of the best tools in personal finance.

And as a final note on credit cards, it’s nice knowing you have a $10,000+ float per card in case of emergency. Especially when some higher end cards have 12+ months with zero interest.

Bold Calls

To be honest, I couldn’t squeeze the pizza lesson in anywhere else. So I’ve created this bonus section and added a few extra bold calls for those that have made it this far.

Domino’s is in the top 5% of pizza options.

Send tweet.

I’m halfway joking here, but I do think Domino’s makes a better pizza for $6 than nearly every $20-$40 pizza I’ve had from popular pizza restaurants. And the same could be said for taco trucks in Austin compared to most of our high end Mexican and Tex-Mex restaurants. Or McDonald’s coffee versus most boutique shops, In-N-Out versus custom burger shops—the list goes on…

I guess the lesson I’m trying to get across here is that restaurant popularity does not equal enjoyment. Don’t be afraid to venture off the path and try restaurants with less hype.

Disclaimer: Some hyped restaurants live up to the hype. Franklin Barbecue and Round Rock Donuts both come to mind here in the ATX area.

The acceleration of staying home is for real.

Technological developments, e-commerce, internet of things, non-gym fitness, and other at-home areas seem to have reached the point of no return. It would be wise to mold your education and career trajectory accordingly.

I’m not saying restaurants, gyms, and traditional retail are dead. They’re definitely not. Just don’t expect a reversion to the norm.

Millennials will boost the life expectancy curve.

Here in the US we’ve seen a fairly flat life expectancy chart since 1990, hovering around the 75-78 year life expectancy. I’m hopeful millennials begin shifting their talents and focus to the life sciences as we age.

With so many technological advancements, it seems like biological technology is lagging behind. I could be totally wrong about this and would love to hear your thoughts if you’re in the know about this topic!

Wrapping Up

Whew, I think that’s plenty of lessons for this decade. Hopefully I can look back on this ten years from now and laugh at how little I knew. I guess that’s part of the beauty of thinking and learning in public.

I’d love to hear about your most important life lessons or answer any questions about the lessons I shared today. Drop a comment below and let’s chat!


Friday 21st of May 2021

Such wisdom you have for such a young pup! You are an inspiration. Keep up the great work!

Mason Woodruff

Wednesday 26th of May 2021

Even the wisest mind has something yet to learn! ;)