HOW TO BE CRAZY AWESOME

5 Reasons to Jump off a Cliff

The old adage is probably going through your head now too… “If everyone else jumped off a cliff, would you?” No, obviously not. But sometimes, jumping is the best thing you can do for yourself. The adage is wrong.

Josh LaMar (He/Him)
10 min readAug 20, 2019

Most of us imagine those big life choices to look something like this image above. Huge sheer cliff face. Big drop. Really scary. That’s where the adage is wrong. Because if we approach big choices in life and we think they are scary, it’s much easier to not go through with them. And the one thing that we should do in those cases is to take a risk, bet on yourself, and let the universe catch you.

All of the most important life choices I’ve made have been big and scary. I was unsure of how it would work out. I was afraid of failing. I didn’t think that I had it in me to go through with it. Self-doubt and negativity easily settle in and arrest our personal development.

So, what did I do each time I was really afraid?

I jumped off the cliff.

And I think you should too. Here’s why.

5 Reasons Why You Should Jump Too

1. It puts the rest of your life into perspective

Things that look big turn out to be much smaller in retrospect. And small things turn out to be incredibly influential. I’m reminded of that famous Steve Jobs quote about the dots…

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.” Steve Jobs, Stanford Commencement Speech, June 2005

I might add: “Even when it takes you so far off the well worn path that you get lost, spend a week going in circles, and then end up at the top of a cliff and the only way out, is running of the ledge.”

When you’re looking into your future, it’s hard to see where it’s going. You have control over right now, but not over a lot of other things. But as you look backwards at your life, the dots connect. The choices seem to make sense and lead from one to another.

It’s only now that I’m almost 40 that I can look back at my 22 year old self and tell a story that makes sense. At the time, I was just following what I was interested in to see if I could somehow make enough money to leave my parents house. Now, I see how the choices I made took me down a path… a path of self discovery. Of learning who I was and pondering who I wanted to be. Of figuring out what I wanted to spend my life doing and what areas would make the most sense for me to work on.

2. You will learn something important about life and about yourself

Steve Jobs continues, “You have to trust in something — your gut, destiny, life, karma, whatever.” I posit that the answer to that something is yourself. You already know the answers you’re looking for. They aren’t, “Out there,” they are, “In here.”

And yet, everyone needs guidance when they feel lost. I know my 22-year-old self was lost trying to figure out what to do with his life. I had just graduated with undergraduate degrees in Music Composition and English Poetry. I had no idea what to do next. I tried to get jobs and got no where.

Sometimes wisdom comes from the least expected place. For me, it came through my involvement in choir. Yup. Choir.

A friend from choir happened to be a therapist. She was very open and giving with her wisdom and I heeded it well. I was living with my parents after undergrad and it really wasn’t the easiest situation. I wanted to get out, but I didn’t have a job. And then an opportunity opened up to live with a different friend who had an extra room… and what did my friend say to me?

Sometimes you just have to jump and know that the universe will catch you.

Wise words from a wise woman. I decided to take that first jump. I moved out of my parents house with everything I owned to a friends spare room. What happened? Well, I had just interviewed for a position at UW Medical Center the day before and I got the phone call in the car LITERALLY 15 minutes after I had left my parents house.

I jumped and the universe caught me.

I look back on this decision and it seems silly. Of course something would work out! But it was my first job out of undergrad and it was after 7 months of being rejected from things like jobs as a barista and clothing stores.

Next, another friend from choir told me about the world of UX. I immediately started looking into the program at UW, then called Technical Communication. This is interesting! I thought. Wow, I had no idea that people could have jobs to do this! I started taking courses for a Certification in Technical Editing and applied to grad school

A year and a half later, after my first quarter of Grad School at UW, I took my next big jump. I finally had a job offer for a contract at Microsoft! But it was only for 1 month.

What did I do?

I quit my job at UW Medical Center to take a 1 month Research contract at Microsoft. And still, the universe caught me. Even though that contract was only a month, I started looking for other contracts afterwards and stumbled into a Web Development contract… which I was offered and accepted. And I loved it.

My 22-year-old self wasn’t really sure about where he wanted his life to go. But by taking these jumps he learned an important lesson: he learned to trust in himself.

3. It isn’t as scary looking back

Trust me… it really isn’t. The part that is scary is not knowing how things will turn out. When I look back at my own story, it doesn’t seem as scary as it was at the time. It all makes sense

Steve Jobs finishes by talking about the path itself: “Follow your heart even when it leads you off the well worn path; and that will make all the difference.” This echoes The Road Not Taken, one of my favorite poems by Robert Frost: “Two roads diverged in a wood, and I — I took the one less traveled by, And that has made all the difference.”

To extend this metaphor a bit, one road leads to normalcy and the mediocre and the other road leads to the sublime.

To stay mediocre, you don’t have to do much at all. Maybe you just sit there thinking about the choice and never make it? Maybe you take the easy road because it’s the one you know. Maybe you end up in your late-30s wondering where half your life went and if this is really all there is?

To reach the sublime, you have to work for it. You have to take the road not taken, off the well worn path, and onto the ledge of the cliff. And then jump.

Two approaches to this:

  1. Sit and think about it a while, maybe jump, and maybe not. If you’re a thinker, or you’re in your head a lot (like me), this is probably where you start.
  2. Run your ass off towards the edge screaming with everything left in you because you’re terrified and thrilled at the same time. This is what I end up doing every time… after thinking too long.

I have actually taken both approaches, but both led me to the same decision: Jump.

Did I waste my time overthinking? Yes.

I did this again recently when I quit my dream job at Microsoft on March 1, 2019. I was happy and successful and I loved my career at Microsoft. I loved my life in Seattle. But over time, I realized that I wanted more out of life. As I’ve been getting older, I have come to value time and quality of life over money and status. How you work is more important than what you do.

I thought about my exit for a while. It was important to me to leave for the right reason: because I was moving towards something amazing. Over the past 5 months, I’ve been taking a sabbatical to reflect on my life and what I want out of my life and what I’m going to do next. I had some ideas that needed time to percolate, but I hadn’t fully committed to them until I quit my dream job. Then, there was no turning back.

Would my 22-year-old self do this? I guess probably he would, since that’s what he did already ;)

4. You’ll stand out from the crowd

When I quit my job, I was immediately enveloped by so much love and support. I honestly didn’t expect that at all. People came out of the woodwork to tell me how inspired they were by hearing my story. People told me they had always wanted to go to Paris, or live in Paris. People called me, “Brave.”

I’d never thought of myself as brave before. But, if you see making a decision like quitting your dream job to move halfway around the world to Paris to take French classes just so you can reflechir on your life, read Sartre, Camus, and Baudelaire, eat croissants, and go to the Louvre…. yeah, it does seem a bit out of the ordinary. And you know what? I love it. It’s been amazing.

I stick out from the crowd because I’m doing something amazing that no one else does. I’m literally living out other people’s dreams. I know this because so many people have told me this. And I am so humbled by that. I just wish that everyone else that wishes they were living their best life would take actions towards making it happen. If you’re ponding that: Do it.

Taking such a huge jump off a cliff is scary and hard and yet incredibly rewarding.

Several years ago, I was introduced to the World Domination Summit by my husband. I remember one specific talk about financial independence that really inspired me. What if I could pay off my student loans? And my car? What if I could be debt free? What if I could take a break from work and have time to think?

The idea of taking a sabbatical for my 40th birthday started to inspire me. And then it became a thing that I was working towards. And then, little by little, I started paying off the loans and getting things together so that when it became the right time, I was ready to take a huge jump.

5. Your life will be crazy amazing

One of the biggest jumps I’ve taken was getting married 3 months after meeting my husband. I was a featured, “Attendee Story,” at the World Domination Summit in 2014 and I think this short talk really gets at the heart of my message:

Be open, because you never know what’s going to happen and sometimes the craziest thing is actually the best thing. (Me)

Word Domination Summit Attendee Story, 2014

Jumping off cliffs is crazy, but sometimes, it’s what we need to grow and to push ourselves outside our comfort zones. This is why I’m in Paris. I’m pushing myself to do something scary. To learn a new language. To live in Europe. To build a new life. To see the world differently. And to make the world a better place.

I truly believe that part of how I can make the world a better place is by helping to make Technology easier to use. I see how people struggle and fail and blame themselves for things that could be easier if we just made technology better. This is why I love working in Research.

And that is what brought me to the 5th big scary crazy Jump: Creating my Research company with my husband: www.amplinate.com

My self reflection has brought me back to believe in myself and come up with another crazy jump. Do I know how everything is going to work out? Nope! But do I believe in myself? Oh yes, definitely. And I also believe the universe will catch me.

Want to have a good life? Take a risk.

Want to have an amazing life? Take a BIG risk and jump.

I think these are exactly inversely proportionate: The more the risk, the more crazy amazing the life.

To Come Full Circle…

If everyone else jumped off a cliff, would you? Hell yes.

Why? Because I’m doing the hardest, scariest, craziest, most difficult and most rewarding thing that I can possibly do in my life. It means that I’m pushing myself to my limit and growing exponentially as a human.

And you can do it too. I’m not special. I’m just a human like the rest of us. I’m scared out of my mind by taking these jumps, but they work out. And I know that if I can do it, anyone can do it.

So what’s the thing that you’re most afraid of right now? Is it also the thing that you want most in life as well?

What’s holding you back?

Now go be crazy amazing. The world needs you.

Josh LaMar is CEO & Co-Founder at Amplinate, a product strategy thought partner committed to helping tech companies save millions by amplifying what resonates with your customers in order to build products that solve real problems.

I want to thank one person in particular for inspiring this post: Erin Baker. Erin is the person that said to me, “You don’t need a life coach, you need to share your story.” This is the beginning of that story.

There have also been a few people who have encouraged me to jump at other points in my life. To them, I also owe a debt of gratitude: Marcelo, Meridith, Eric, Erica, LiAnne, Christian, and Sara. You are my tribe, my cheerleaders, and my friends.

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Josh LaMar (He/Him)

Co-Founder & CEO @ Amplinate.com, UX Strategy Consultant, and Technology Thinker and Writer