30 Things I've Learned About Life and Business in Each of My 30 Years

By Sean Ogle •  Updated: 04/07/15 •  21 min read

Well, it’s official: I’m old.

Ok, I’m not that old, but over the weekend I had my 30th birthday.

That number always seemed so far away, and then out of nowhere, it’s like wait? I turn 30 next month?? How did that happen.

The good news is I’ve been repeatedly reminded that 30 is one of the best decades, and based on how things are shaping up so far – I’m inclined to agree.

A Quick Thank You

Before I jump into this post, I thought this would be a good opportunity to simply say thank you. 

The work I do is not a right, but a privilege. Everyday I realize how lucky I am and I try to take nothing about my lifestyle for granted – and help as many people as a I can with their own goals.

Many of you have been following this blog since day one, and even though things have changed dramatically the core message is still the same: Build something that lets you do more of the things that make you happy.

30 Years of Lessons

For the past couple weeks I’ve been thinking about some of the most important lessons I’ve learned over the years. Some might seem trite and irrelevant, others are more grandiose conclusions – but hopefully there are a couple things I’ve learned along the way that will be useful in your own journey.

This year I wanted to mix it up and do something at least a little bit different. Rather than just share 30 random lessons I’ve learned, I thought it would be more interesting to reflect back on my whole life, and share one lesson I’ve learned each year.

Starting with year 1. 1985.

Some of the most important lessons I’ve learned happened a long time ago, so now it’s time to give credit where it’s due.

FYI: This is a much longer post than usual…sorry about that!

Year 1: You don’t have to do everything on your own

There are adults I know who still haven’t learned this lesson! We all need a little help from time to time, and in the case of my one year old self, I needed help all of the time. 

Even if I’m slightly more independent, this is still a good reminder.

Year 2: You can say a lot without speaking

I don’t honestly remember if I could talk when I was 2, but I’ll assume whatever I could say was pretty limited.

Sometimes we need to get creative to get our point across. Whether it’s our body languag or medium of delivery (blog post, letter, video etc) – sometimes the most effective ways to communicate a message are the least obvious.

This kid gets it:

Year 3: Before you can walk you have to crawl

I try and teach people in Location Rebel all the time, don’t just jump straight to the sexy, passive income business. You need to start with the basics if you want to have long term success.

These are some of the essential skills you should begin learning before trying to build your passive empire.

Year 4: Never let your mom cut your hair

The photo pretty much says it all.

She called it the "Macgyver" Hair cut

She called it the “Macgyver” Hair cut

Year 5: Music can help any situation

When I was 5 I got my first walkman, complete with cassettes of C&C Music Factory and MC Hammer. I took that thing everywhere.

It doesn’t matter if I’m sad, happy, nostalgic, trying to be productive – whatever, there’s music out there that helps.

For focus, I strongly recommend Focus@Will.

Year 6: Sometimes big changes in life are necessary, even when it scares the hell out of you.

When I was 6, I moved from Georgia to Oregon. Even at a young age it’s a little scary going to a new place, a new school, and meeting new kids.

Yet, my life would be 100% different today were it not for that move.

So even if everyone was a little scared, it still led to some amazing things.

Year 7: You never know when you might meet someone who will change your life

In second grade I met a lot of people that continue to be some of my best friends today. It’s often in the most unexpected places that you’ll meet a friend for life, so always be open to conversation and meeting new people.

Friends from elementary school at my 30th birthday party last weekend.

Friends from elementary school at my 30th birthday party last weekend.

Year 8: A small gift can go a long way

On my 8th birthday, we were living in a relatively new house, and I didn’t really know many kids in the neighborhood that well.

I remember telling the girl across the street that it was my birthday, she ran inside, and came back out and handed me a cool old stop watch and said “happy birthday!”

Apparently it was actually pretty valuable and a few days later her mom traded it with me for a cool new digital one she bought me.

I have no idea why I remember that story 22 years later, but that’s just the point: an unexpected gift can stick with you for a long time.

Year 9: Practice doesn’t make perfect, but it can make you much better than you are

Nobody is perfect…at anything – so the saying “practice makes perfect” is a bit of a lie. However it can make you much better than you are.

As of this week I’ve officially crossed off one of my bucket list items: to become a single digit handicap.

When I was 9 I wasn’t a golfer though, I was a tennis player. I used to go down to the local school and hit tennis balls against the backboard all the time. I practiced a lot and even though I was never the best I got to be a pretty damn good tennis player.

Year 10: The underdog can win. And often does.

5th grade was a year that had a bit of foreshadowing to my future life.

I was known as “Mr. Geography” in my class because I could recite all of the state capitals, and generally just took a big interest in travel and the world.

Somehow as a 5th grader I got entered into a geography competition for 6-8th graders. We had to give a presentation on a historic destination of our choice and then the best presentations got awards.

I borrowed my teacher’s slides from her trip to Pompeii and gave a whole presentation on the eruption of Mt. Vesuvius and how Pompeii came to be.

I won first prize after they had to make an exception to let me into the event.

No one expected the shy 5th grader to come out with the W – but the underdog can win – and often does. So don’t use that as an excuse for not getting in the game.

Year 11:  Not everyone will like you, and that’s ok.

Middle school for me was a bit of an awkward stage – like it is for most kids. I had a pretty close group of friends, but even then I was kind of the one they picked on.

Some kids would hardly give me the time of day. It’s always tough when you want to fit in, but the world won’t let you.

Looking back this was the year I learned that this was a good thing. If everyone likes you you’re probably doing something wrong. So embrace your friends, and don’t worry about the haters. If you’re going to live a fulfilling and unconventional life, there will always be those people who hate you for it.

Year 12: Travel experiences will last a lifetime

In 7th grade I took a class called “Starquest.” It was technically a science class, but in March every year the class takes an 8 day trip to Disney World to actually see the things we were learning about in a hands on way.

To this day it’s one of my oldest and best memories of travel.

That photo up above from my birthday party? All four of us were on that trip, and we could all go on for hours about stories from it.

Being able to experience travel with someone else is one of the best ways to form a bond with them.

Year 13: Rejection is a part of life. Embrace it.

In 8th grade I had a huge crush on a girl named April.

It was one of the last dances of the year and I couldn’t get the guts to ask her to dance, so I asked one of her friends instead.

She came back and basically said no.

I was heartbroken. Ok, maybe not heartbroken, but at least a little embarrassed.

I’ve learned over the years that if you’re not getting rejected, you’re either not trying hard enough, or not thinking big enough. Rejection can be a good thing.

Just ask Jia Jiang:

Year 14: Uncomfortable situations are where the most growth happens

I started high school when I was 14. That’s a scary thing for anyone.

You go from being on top to the very bottom over the course of a summer, and yet despite the uncomfortableness this can provide, high school is arguably the time where the most growth happens.

Since then every new uncomfortable situation has led to amazing things:

The list goes on.

Most people will choose comfort over uncertainty – and many of those people will always feel like something is missing in their life.

Take a chance and go through a period of discomfort if it means you really think the juice will be worth the squeeze.

Rapping your own version of the Fresh Prince of Bel-Air in front of a sold out crowd in the biggest theater in Portland? Yeah, that’s pretty uncomfortable…

Sean Ogle WDS

Year 15:  Putting trust in people to figure things out for themselves can lead to a lifetime of autonomy.

When I turned 15 I got my drivers permit. My dad took me down to take the test, and after passing, he tossed me the keys and said “drive us home!”

Within seconds I’d been honked at twice, but I got back unscathed.

Now that I can drive I have complete autonomy.

This same thing applies to business.

You don’t have to do everything yourself, and by trusting in others to do their job and help grow your business, it can be freeing for you, and allow you to spend more time focusing on the things that matter most to you in your life and business.

Year 16: Everyone should take at least one epic road trip in their life

The summer after my sophomore year in high school I convinced my parents to let me drive down to Vegas and California with two of my friends.

It took a lot of convincing, but the result is one of my best memories of high school. We stopped through Tahoe, explored the Vegas strip, went to Magic Mount in LA and much more.

Since then I’ve taken a few other big road trips (see here and here), and I have incredible memories from all of them.

Year 17: Consistency is the number one key to success

District Champs! On the way to state :)

District Champs! On the way to state 🙂

Between the ages of 8 and 17 I played a lot of tennis. I was also really consistent with it. I played 3-4 times a week for a decade.

Eventually that leads to success.

When I was 17 I won districts and went on to get 3rd place in the State.

I think the same lesson can be applied to blogging. I don’t know anyone who has consistently blogged for 5 years and not achieved some level of success.

Most people stop before they get the one big hit that helps it to take off, but that’s all it takes – one turning point. The only way you’re going to get there is through consistent effort.

Year 18: It may not always seem like it, but in time you’ll realize who your true friends are.

It’s a long story, but right after my high school graduation some of my best friends stopped talking to me. It was very much a high school thing, but it made for a really rough summer.

In the end, there were a couple people who put all of that stuff aside and still hung out with me.

It turns out the people who I thought were my best friends, weren’t, while others who I didn’t think I was as close with, turned out to be friends for life.

When I left my job to start my business and move to Thailand, I was at another one of these turning points and I wondered who my real friends would be. Fortunately, most of them were really supportive.

Year 19: Your attitude, during both good and bad times, is a choice

This is one of the most important lessons I’ve ever learned.

During this time I was dealing with my parents splitting up and generally had a lot of negative things going on.

My whole life I’ve been a pretty positive, glass half-full person.

To be honest, I think it’s my best trait.

No matter how rough or stressful things get you always have a choice in how you react and your attitude towards things.

It’s certainly not always easy to have a positive attitude during dark times, but you can do it.

Always remember that it’s up to you how you react and how to perceive things, and that is often the most important determining factor in how a situation resolves itself.

Year 20: Higher education is great for certain people. But there are many much more affordable options that may be a better fit for young and old students alike.

My second year into college I still wasn’t taking any of the classes for my chosen major, and many of the classes I was taking just seemed like exercises in learning how to study.

There’s something to be said for that, but I didn’t need to spend over $50k to learn that.

Here’s one of the very first posts on this site about college: How to Create Your Own College Education

I wouldn’t trade my college experience, I had a fantastic time. But I also recognize you can learn much more relevant information for your interests for significantly less money.

Location Rebel is an excellent example of that.

Year 21: Alcohol can be a wonderful tool, or a deadly weapon. Treat it as such.

Alcohol can be a great thing. It can be a good way to bond with friends and family, as well as a great medium with which to meet new people and enhance shared experiences.

It can also cause people to do incredibly stupid things, lead to addiction, and ruin lives.

When I turned 21 I saw both sides of this during my last year in college. It led to a lot of fun times, but I also saw it ruin kids lives extremely quickly.

Know yourself, and be responsible.

Year 22: It’s important to surround yourself with likeminded people. It’s just as important to surround yourself with those that think differently.

As I was beginning my first year in my real job I was also starting to think about where I wanted to go. Who did I want to be around? Was I looking for a job or did I want to own a business?

As the seeds were slowly being planted for a business of my own, I needed to meet and be around other entrepreneurs.

But over the years I also found it’s just as important to have people in your life that think differently and have different goals. It not only makes you more well rounded, but I think it’s important to have a friends where you don’t always talk about work.

The opposite holds also true, if you’re looking to build a business, you need to have other entrepreneurs in your life! There should always be a balance.

Year 23: Routine isn’t a bad thing. Except when it is.

Sean Ogle in a suit and tie

Me at the height of my quarter life crisis

These days I have plenty of routines in my life. From my morning coffee to the music I turn on, to the weekly round of golf.

These a few are routines that lead to health, happiness, and business success.

When I was 23 I was experiencing the other side of this. Day in and day out I’d put on my suit, drive to work, and not feel like I was making a difference.

I was bored, had wanderlust and didn’t feel as though I was getting any closer to satiating those things.

Blind routine is a scary thing, because you can get so wrapped up in it that 20 years later you wonder “how did I end up here?”

Deliberate routine can change your life. Be aware of your routines and make sure you’re always building your life around ones that will help you move things forward.

Year 24: A quest is an essential part of a fulfilling life

On top of the South Sister in Central Oregon

Climb a mountain;: One of the first things I crossed off the bucket list.

When I was 24 I created Location 180. I used my bucket list as a way of holding myself accountable for the things I wanted to do in life.

Those goals have helped to keep me on track and make sure I’m always striving to reach my goal of “living a life worth writing about.”

More recently I began my quest to play the top 100 golf courses in the world. It feels even more daunting, yet it gives me direction, is exciting, and can give travel and business goals a purpose.

Year 25: Master the craft, not the form

Sowden House in Los Feliz, California

The Sowden House, where we hung out with Orlando Jones.

This was a crazy year. I moved to Thailand. Moved back from Thailand. And had a bunch of crazy adventures.

One of the most notable was the time rented an incredible house in LA and invited me down for a week. Oh, and then the day Orlando Jones randomly walked into the living room and we spent the entire night hanging out with him.

One of the things he said will always stick with me: “master the craft, not the form.”

For example you don’t need to master being a blogger. Rather you need to master the craft of writing, or even better, the craft of story telling.

When you do this your options are infinitely more interesting.

Year 26: Experiences > Stuff

W Hotel Bali

The W in Bali had great wifi

While I was 26 I had one of the coolest adventures of my life and lived in Bali for 2 months. It was an incredible experience, and it helped to solidify the idea that experiences are worth more than stuff.

I’ve had the good fortune of doing a lot of travel over the past few years and I cherish my memories of those trips much more than material items.

I’m by no means a minimalist, in fact you could say I’m the exact opposite, but I still will always choose a grand adventure or experience over a new flat screen.

Year 27: Life is fragile. Make the most of it.

While everything was great with my own life this year, both my fiancee Tate and I learned a hard lesson when two good friends of ours died in completely unrelated incidents.

Both were some of the most happy, adventurous, and fun loving people you could ever hope to meet.

Katie died in an avalanche, and Erin in a plane crash.

Both of these were extremely difficult to accept and deal with because it was so close to home. It could have been any one of us.

I think about both Erin and Katie often, and when faced with the decision of “do or do not” I think of them, and always try and do more. 

Year 28: The more you say you’re going to do something out loud, the more likely it is to happen

Playing Whistling Straits on my first golf road trip. Home of this years PGA Championship and one of the best courses in the world.

Playing Whistling Straits on my first golf road trip. Home of this years PGA Championship and one of the best courses in the world.

I’ve found myself in a habit of saying I’m going to do something before I actually think it’s ever going to happen.

A couple years ago I said I was going to take an epic golf road trip and play 14 top courses in 14 days.

I talked about it for a few months and then called up a couple courses to see if we could work out a deal. We did, so I booked a ticket and the trip just kind of materialized.

If you say you’re going to do something enough, eventually it just kind of happens.

A couple months ago Tate and I flew to Vietnam to get suits tailored for my groomsmen. I’d joked about it for years, but never actually thought it would happen.

Year 29: Just because you’ve “settled down” doesn’t mean you have to settle down

In front of our new house - 30 seconds before I proposed.

In front of our new house – 30 seconds before I proposed.

If you’re looking at last year from the outside you might be tempted to think I’d settled down. I got engaged and bought a house here in Portland.

The reality is I still travel just as much as I always have, and continue to enjoy the freedom this lifestyle provides.

Just because you do some of the things traditionally associated with “settling down” doesn’t mean that has to be the case.

The house was a very deliberate decision designed to enhance the flexible lifestyle I’ve created. And it’s done exactly that.

Already this year I’m on pace to travel more than I have in a few years – but while I’m at home, I’m much more comfortable and productive. Not to mention its shaping up to me a pretty good investment!

Year 30: At any given time, do the thing that will make you happiest

Sean Laptop Vail

I came this this realization last month. Why do I generally live a pretty happy life?

One of the key reasons is pretty simple: I do what I want. I try not to do the things I feel like I should do, or that other people think I should do.

If I want to work, I work.

If I want to play, I play.

It took a ski vacation to Vail to come to this realization.

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The Next Thirty

I get asked pretty frequently what the next 2, 5, even 10 years look like.

The honest answer is I have no idea.

I’m working now to make Location Rebel as good as it can possibly be. It’s the best tool I have right now for making a difference in the lives of others.

I don’t think you always need to know where your destination is, you just have to make sure you’re on the right highway. I know the things I’m doing now are going to benefit me in whatever capacity I decide to morph my life and business into over the coming years.

I hope at least one of these life lessons has sparked something in you, and once again I can’t thank you enough for the support you’ve shown over the years.

I’ll continue writing here for as long as you continue reading!

To help bring me into my 4th decade I’d love if you could share one of two things in the comments:

  1. One piece of advice you’d give me for my next decade
  2. One life lesson you’ve learned that’s had a huge impact on you.

Can’t wait to see what you come up with!

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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