As I write this post, I was brought into this world 30 years ago today.

Even though 30 is apparently the new 20, and some days I feel like my real life is just starting to get interesting, I find myself reflecting on the experiences of the last 30 years, and all of the lessons I’ve managed to learn along the way.

So here they are, (well 30 of them at least) categorized to help readability, but in no particular order of importance.

Money Lessons

1. Pay Yourself First

Every time you get paid, whether its a weekly paycheck, a side job, a gift, an inheritance, or anything of the like, put some of it away the first thing you do. Don’t even consider that part of your income. It goes into savings for a large purchase goal. Otherwise, it’s human nature to want to spend it.

Even better – automate the transaction straight from your account. This way you won’t have to go through the emotional transaction, and will put your saving on autopilot.

This will help you save some nice large chunks of money over time that you can spend on possessions and experiences that significantly enhance your life, not petty materialistic things that often become a burden.

2. You Can Always Earn More

Almost every financial “expert” out there will tell you the best way to save money is to cut back on your “unnecessary daily spending.” These are things like eating out, your morning coffee, and other things you like to do.

But here’s the thing. Not only do you have to make the emotional decision to cut out those things every single day of your life, but you can only cut out so much from your life until it just starts to really suck.

At that point, you’re not just living on ramen and tuna fish, stealing your neighbor’s WiFi, and drinking nothing but water, but you’re also putting yourself in a very poor financial mindset. If all you do is cut back on your spending, you’ll never be driven to succeed.

You can always earn more though. Your income potential is limited only by your drive to earn. So rather than sacrificing your entire life, figure out how to enhance your lifestyle through large financial wins, and earning more.

3. Pay Off High Interest Debt

Before I paid off my students loans from graduate school, I hated looking at the interest I was going to have to pay. It was going to cost me thousands of extra dollars over just a few years. Fortunately I was able to pay it off pretty quickly.

That said, mine wasn’t that bad relative to what some people pay. Being stuck with 15-20% interest rates can be crippling. That can equal tens of thousands of dollars in interest for only a few thousand dollars of debt. But if that’s where you are, then you’d better get control of your spending habits and get cracking on paying it off. Otherwise you’re going to be kicking and screaming just to keep your financial head above water.

Take a financial snapshot, isolate the highest interest debt chunk you have, streamline your finances, and start pumping money towards that puppy – preferably in an automated fashion. It may take some time, but trust me, you’ll feel much better when you do and it’ll be A LOT easier to get approved for loans when you need them.

4. A Little Money Can Become A Lot of Money

I’m fortunate to have a financially motivated mind, so I was interested in personal finance at an early age. I’ve been investing since I was 18, just a little bit per month, and sometimes in large chunks as finances allowed.

Do your future self a favor, and open a Roth IRA. Even if you’ve only got the capacity to save $25 a month, it’s better than nothing at all. That money will add up over time, and will begin to grow and compound nicely in a few years. It might not seem like a smart move early on when you need money in your 20s, but trust me, as you get into your 30s you’ll be glad you started early.

Also, target employers with aggressive 401k plans who offer to match your contributions, and possibly even profit share. These plans are amazingly lucrative and can easily turn you into a millionaire over time.

The lingering question to ask yourself here is… Do you want to spend everything you have now and work another 20 years when you’re 50, or have a little less spending money and retire while you still have some life left?

5. Keep Your Finances Hands Off

Some people might like to babysit their investments all day long, but not me. It’s actually proven that the vast majority of actively managed portfolios fail to outperform the market. Unless you’re a financial savant, why bother? I can think of better things to do.

Check out a type of hands off investment called ‘lifecycle funds.’ You can buy into these once, usually for very cheap, and then auto-invest each month. They’ll even adjust their risk patterns as you age – higher risk when you are young and have time to make it back, and lower risk when you are older and need to protect your money.

They’re also usually very stable because they tend to mirror top indexes. This keeps you from having to babysit them in case of daily market fluctuations that can sometimes freak out neophyte investors.

6. Subscriptions Silently Suck

Monthly subscriptions, especially those that are auto-billed and auto-renewed were one of the best things ever conceived. It allows large transactions to become small ones, and emotional pain of paying to completely go away. Because of this, A LOT of people have several subscriptions they don’t even use, and sometimes don’t even know about.

Take some time to sit down and review your monthly subscriptions (check for any annual ones as well). This is one of those low-hanging fruit personal finance optimization items you can take care of one time a year, and potentially save yourself hundreds of dollars to put towards other more important things in your life.

7. Money Is Great, But Experiences Are Priceless

Being from a frugal background (I grew up in a small town without a lot of money), I have a tendency to get caught up in accumulating wealth. That sometimes results in a lack of life experiences.

But at the end of the day, a giant chunk of money in the bank isn’t anything you can remember or reflect upon. It’s the trips I’ve taken, the sights I’ve seen, and the experiences I’ve had with close friends that I have come to value the most. You can always earn more money, but you can never get back your time.

Make sure to take time to enjoy what you have worked for.

8. Learn to Negotiate

Negotiation is awkward, but it can save you thousands if not tens of thousands over the course of your life. Read a couple of books on the subject and put those ideas into practice. This is a great skill to possess for those large financial wins in life.

Mindset Lessons



Photo by Jonathan Kos-Read

9. Think and Act For Yourself

Most people follow the herd. They don’t even really know why they do the things they do. They just live their life according to how society says it should be lived. Nonsense.

I say do what you want. If you’re going to act a certain way, do it because it makes sense in your mind, not just because “that’s the way it’s always been”, or “that’s just what you’re supposed to do.” That’s a recipe for mediocrity.

Following the herd is only going to get your as far as where the herd stops, and for most people, that’s nowhere near the top. Pave your own way.

10. Don’t Take Life Too Seriously

Business dealings are serious. Dental exams are serious. Raiders fans are serious. But most things in life should be enjoyed. Laugh, smile, joke, and have fun with your life. No one likes a Grumpy Gus, so learn to be free of negativity and live a life of happiness with those around you.

11. You Are What You Believe

If you truly believe you will succeed, you will find a way to do so, but if you convince yourself you will fail, you most certainly will do so as well.

You are the image you hold of yourself in your mind. If you want to be successful, it is your job in life to build that image up to be successful, healthy, compassionate, humble, and any other trait you would like it to possess.

12. Your Environment Shapes Who You Are

In five years, you will be the average of your five closest friends, your life experiences, and the environment you surround yourself with along the way.

What you choose to let into your mind on a daily basis shapes the way you live, act, and think. That is why it is imperative that you create a positive and supportive environment for yourself. Live in a world of negativity, and you will be a negative person. But live in a world of positivity and support, and your subconscious mind will follow suit.

Seek inspiration, motivation, mentors, and new experiences. They’ll certainly help to contribute to that average.

13. You Have Control

Bad things happen from time to time, even to good people. I have a friend who, about 18 months ago as I write this, was just about to open a CrossFit gym. Then his house got hit by a horrific tornado.

He could have easily cried “why me?”, thrown in the towel, and put his business off for another year, but he didn’t. He realized he had control of how he reacted. He got together what he needed and opened his business anyway, and now it’s a thriving success.

My point is, your life is not defined by the circumstances which you face. Your life is defined by how you react to those circumstances. You have control over everything in your life one way or another. The choice to act is always yours.

14. Think Bigger

You won’t get rich by raising chickens and selling organic eggs for $3 a dozen. If you always think in terms of making a ‘few extra dollars’ you will only make a few extra dollars. We tend to reach the goals we set for ourselves, and not too much more.

Don’t set a goal to sell 1,000 copies of your book. Set a goal to sell 100,000. If you think bigger and truly believe in yourself, your mind will figure out ways to make your visualization happen.

Productivity Lessons



Photo by J L

15. Motivation Contains Inertia

When you become motivated, act on it. It’s much easier to maintain a high level of motivation while you’re moving than it is while you’re sitting on your butt. Just like Newton’s law of inertia, we have a tendency to stay motivated if we are already motivated.

16. Find Something to Focus On

I’m what they call a serial learner – or someone with a very high theoretical quotient – so I have a tendency to want to learn and do a lot of different things. This has its ups in terms of gaining a wide variety of skill sets, but it has hurt me in terms of specialization.

I’ve created a lot of things (two six figure businesses, two books, several training courses, countless websites, etc), but haven’t yet stuck to something long enough to build something totally amazing, although I’m getting there with Academy Success.

Find something that really matters to you, that brings you joy to do, and helps others. Always keep the image in your mind of what it will eventually be, not what it is right now. That will help you focus on doing what needs to be done to build it.

17. Keep Your Priorities Straight

If you want to finish the large projects you start, you have to keep those projects at the top of your priority list. As time goes on, new projects have a tendency to become the ‘flavor of the week.’ You can get distracted by the newness of them and lose focus on what really matters to you.

If you start something and find yourself getting distracted, remind yourself of the benefit of why you started it in the first place. This will help you focus on it until it’s finished.

18. Your Time is Precious and Finite

I used to think that it was lazy to pay people to do things for me, but as I began to realize how much I wanted to do in this world, I found myself needing to streamline my life because I only had so much time in each day.

But I didn’t want to lose productivity either. Eventually I realized that I could drastically optimize my time by outsourcing, automating, and eliminating to make sure I focused on the things that only I could do, and what was really important to me to accomplish.

Realize and understand that you’ll never get the time back you spend each day. Spend it wisely, because once it’s gone, it’s gone.

19. Be Comfortable, But Not Too Comfortable

There’s this saying that goes, “step outside of your comfort zone,” that I’ve always thought was a little silly. I mean who wants to be uncomfortable all the time? Not me.

Be comfortable most of the time, but every now and again, if you really want to improve, challenge yourself to do something that you’ve never done before – something that you really want to do.

When I developed Output Overdrive, it was pretty uncomfortable. Speaking on camera and putting myself out there to the world was admittedly foreign to me. But I did it because I wanted to do something positive for my readers, and continue to build my online business.

After a while, it because much easier, and started to even feel comfortable. If you just creep out on the edge of your comfort zone every now and then, you can expand it plenty to be successful. If you’re out of it all the time, you’re literally going to work yourself to death.

20. Do Active Things Often

Look at any highly successful person. They’re probably in pretty decent shape. Maybe they’re not throwing down tomahawk dunks, but I bet you they have a regular activity routine.

Richard Branson, owner of Virgin Airlines and about a billion other companies, says working out is the ultimate productivity hack. It heightens every chemical in our body that controls productivity. Blood flow increases, cognition increases, awareness increases – and over time your body gets used to operating at a high level all the time.

This is how highly successful people sustain such high energy and motivation. Whether it’s touch football with your friends, CrossFit on your lunch hour, or a run before or after your day, just do something active on a regular basis. You’ll skyrocket your productivity.

21. Always Be Improving

Learning does not end when you’re finished with school. To continue to grow and succeed, you must continue to sharpen your mind and skills throughout your entire life. The acquisition and execution of valuable skills is largely what separates success from failure.

Learning is easy when you’re young. You’ve got all the time in the world. But as you move into your 20s, 30s and beyond, the art of time management is more and more important, as you must maximize the use of your time to continue to improve while you also live your life.

One of the best investments in yourself you can make is learning how to spend your time the most effectively.

22. Find a Better Way

You’ll see this all over my website and all throughout my Output Overdrive course as well. There is almost always a better way.

Challenge paradigms. Just because something is done a certain way doesn’t make it correct, and on the flip side of that – just because something has never been done before, doesn’t make it wrong.

If Steve Jobs had never challenged the convention of dozens of buttons on music players, we wouldn’t have iPhones as we know them today.

If Airbnb hadn’t challenged the convention of lodging, thousands of people all over the world wouldn’t be renting their spare space for extra income.

If I hadn’t challenged the way gifts are given in my family, I wouldn’t have gone on two super sweet free vacations last year.

My point is – the best ideas are usually completely unconventional, because if they weren’t they would have already been thought of. If you think you have a good idea, don’t be afraid to be act on it, because there is almost always a better way.

Miscellaneous Lessons



Photo by Yasin Hassan

23. Relationships Are King

I’m not insanely socially awkward or anything, but I’m also not a full extrovert networking type of dude. For those of you who know me, you know I like time to myself and value peace and quiet.

This has hurt me in developing relationships because I’m not a naturally outgoing type of person. I have to work at it. But what I have realized is that in terms of success, it’s good to know people, especially other successful people. Not only can you learn from and be motivated by their success and experience, but you can also open yourself up to their networks as well.

I don’t want to sound too self-serving here by any means. This is just how the world works. Make sure to contribute to helping those you meet out as well. Relationships are a two way street. Otherwise they’re not relationships.

24. Listen to Your Parents

Even though there are 20-30 years that separate you and your parents, and you sometimes feel like they’re living in a different dimension, they’ve got a lot of life experience on you, and can often offer some great words of wisdom, especially in your times of need. Keep your relationships alive with them, especially as you get older. The time you spend with them becomes more and more precious.

25. Stop to Appreciate the World

I admit I don’t do this enough, but invariably when I remember to stop and appreciate all of the good things that I have going in my life, I get a feeling of accomplishment and serenity. Even if things are a bit rough at the moment, positive thinking helps to keep things in perspective, and it keeps your mental focus away from the temporary negatives you may be facing.

26. Learn to Understand and Forgive

Stuff happens. If someone does you wrong, or makes a mistake, try to understand that maybe they weren’t thinking clearly, or maybe the circumstances were out of their control. Even if you don’t agree with their judgment, try to understand and forgive what they are going through. It’ll really help bring peace to your life.

And just as you must learn to forgive others, you must also learn to forgive yourself. People have a tendency to dwell on failures and shortcomings, but this will only hinder your output. Take a few moments to forgive yourself and breathe easily. It’ll help you get past what you may have screwed up.

Just be careful not to forgive the same thing more than a few times. At that point it may be time for a change.

27. You Only Have So Much Discipline

People tend to think “if I just try harder than everyone else, then I will be the best.” Sorry, that’s just not the case. If everyone could simply ‘try harder’ then we would all be smashing successes. It’s not trying harder that gets certain people ahead. See, we all have this discipline ceiling that we hit eventually. At that time, we have to shut down. We have no more will power to keep on keeping on.

Successful individuals have figured out how to never hit this ceiling. They make things easier on themselves by setting up their routines efficiently. They outsource what they don’t like to do or aren’t good at. They automate and eliminate anything they can. And they take ‘cheat days’ and downtime when they need it.

This makes it so they can live stress free, get a lot done, and never really have to “try” all that hard.

28. Shut Down Now and Again

Coming from a productivity blogger, this might sound a little strange, but you should take some time to turn yourself off now and again. Being in an ‘always on’ frame of mind will eventually take its toll on your body and mind. To stay sharp for the long-term, take at least half a day each week to just veg out and do nothing.

Whether you’re relaxing outside, or just crushing a Netflix marathon, just make sure you stay away from your normal daily activities. This will help you reset and come back fresh.

29. Learn to Let Go

From time to time, you will outgrow certain people and environments in your life. If you want to keep striving forward, you must sometimes let these things go from your life to make room for the greater things you desire.

30. Grammar Ain’t That Important

My 5th grade teacher would slap me with a ruler for how I just introduced this point :) But the thing is, unless you’re a conservative journalist, proper grammar just isn’t that big of a deal. I probably made a dozen or more grammar mistakes in this post alone, but you’re still reading it aren’t you? And it’s still helping the world.

If you’re a writer, don’t fret about proper grammar all the time. Just be you and express yourself so the world can see who you really are.

If you disagree with that, you probably shouldn’t be reading my shit anyway. ;)

31. Give Without Expectations

A lot of people like to keep score when they do something for someone. I get it. It’s human nature to keep a tally. It helps us gauge the value in what we do. But it can be harmful too. Too much keeping score can result in a cold self-centered outlook.

Sometimes you should just give because it’s the right thing to do. Sometimes you should just help out because people need you. It’ll also make you a better person.

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Now It’s Your Turn

Okay so that was 31. Sorry, I got on a roll. ;)

Now – If you read this far, hopefully a few of those hit home with you and you’re now a wiser person. If so, I would like to ask three things of you to prove it.

One, tell me happy birthday, because well.. I’m old now and I need your love to keep my youth alive. :)

Second, tell me which lesson(s) you liked the best, or let me know what I forgot. I promise to read every single comment.

And third, share this on your networks to help get the word out.

Photo 1/4 by Marina Caprara