Painful Authenticity: 35 Honest Personal Stories, Fears & Facts You Don’t Know About Me

Painful Authenticity: 35 Honest Personal Stories, Fears & Facts You Don’t Know About Me


“Be honestly and unapologetically you. Because you being uniquely you will allow the people you interact with to feel comfortable being uniquely them – perhaps for the first time in their lives. There is no more authentic way to connect and no greater gift to give.”

 – Scott Dinsmore


An Important Note on Respect: Today I’m going to take a leap of faith – and share some things with you that I’ve never shared in public.

While a few were fun to write, many of them were not easy for me to publish. I hope they give you a little better feel for the real side of Scott Dinsmore and Live Your Legend. I know that this post is pretty in-depth (I didn’t want to hold anything back), so if you’re pressed for time, please just read the below intro and then the heading of each of the 35 points below. That will take about 3 minutes. You can come back for the rest later.

This is me being me. All I ask is that you be yourself in return. Please share one story or little-known fact about yourself in the comments.

Now for the fun…


Being Yourself Frees Others to do the Same

Last night Chelsea and I had a delicious three-course and four-hour Greek meal at Kokkari, our favorite restaurant in San Francisco. We were treated by two very gracious and really entertaining LYL and Connect with Anyone members, Brandon and Virginia, who were visiting from Toronto.

I thought the meal might last an hour or two, but we actually totally hit it off and had a blast. Crazy how many things we all had in common.

At about hour three, Brandon looked over at me and said “You know Scott, I was really nervous before our meal, but it’s amazing how comfortable this has been and how real you actually are.”

I looked at him and laughed wondering what he expected…

But it got me thinking.

So much of the public world of entrepreneurs, authors, CEO’s and leaders is masked by a huge coat of bullsh*t.

People seem to want to put off this image like they’re perfect. And it’s often out of fear that the people who respect them won’t love them anymore if they show their true colors.

So they paint a false picture and do a huge disservice to everyone who looks up to them and to the world as a whole. By putting up this front, they create these expectations that are impossible to meet. It’s not fair and it’s downright selfish.

At Live Your Legend, I’ve always tried to be as open, clear and real as possible. To share the warts alongside the glory.

But I’ve realized that for the most part, the public image of LYL and Scott Dinsmore almost only showcases the positive. (but certainly not entirely, just have a look at Full Disclosure: 12 Reasons You Probably Shouldn’t Be An Entrepreneur – The story no one tells)

So today I wanted to share a bit more of myself. Some of the good, the bad, the funny and the ugly things about my life and past in a effort to bring us all closer together.

I’m hoping that it will allow you to feel a little more comfortable in sharing who you actually are with our community.

Because when you show who you really are to someone else, it often encourages them to be themselves as well. And sadly, in a world of false images and representations, many people have never gotten the chance to be uniquely who they actually are.

There is no greater gift you can give.

And as it turns out, there is no other way to genuinely connect with those around you.

Authenticity is at the heart of all things successful.

It’s the foundation of a bestseller.

The heart of an inspiring speech.

The core of a business out to change the world.

It’s also the most powerful way to connect as a writer.

And given that nearly 4,000 of you have joined our Start A Blog Challenge, I could not think of any better timing.

It’s so easy today to puff out our chest and act like we have it all figured out.

We only post the best things on Facebook and Twitter, only write blog entries about our crazy experiences, and when we’re out, we try to look our best. Then no one (except maybe those closest to us) gets to see what happens when we get home some nights and lay awake terrified. Only a very few see that we can’t sleep because we don’t know how we’re going to make something work.

But that doesn’t create genuine connection. In fact, it makes people resent you.

So this is how simple it is – be who you are. Not who you want to be or who you think you should be.

Just tell and share your stories and watch what happens.

I’ll go first.

So now it’s time to get real.

You ready?

Here goes…

Special thanks to my good friends Corbett Barr and Lissa Rankin who have recently inspired a new level of authenticity into the way I live and show up in the world (and a big thanks to all the friends and mentors online and off who constantly hold me to that higher standard – you know who you are).  

35 Honest Stories, Fears & Facts I Kinda Wish You Didn’t Know About Me

1. I’m late. Way more than I’d like to be.

And I can’t stand it. I just always try to do things right up until the last minute, and I notoriously underestimate how long everything will take. I’d like to say that I’m incredibly optimistic about what I can accomplish in a day, but if I’m honest, I know that being late hurts me and others. Especially my wife Chelsea, who deals with it way more often than she should have to. It’s something I work on a lot and the past year has gotten better, but I have a long way to go.

2. I love “Chick Flicks”.

I own a copy of The Notebook and watch Love Actually and The Holiday every year. I’m usually the one twisting Chelsea’s arm to watch these instead of the other way around. Growing up with a sister four years my senior will do that to you. I know just about every word in Girls Just Want to Have Fun. Thanks Kristen!

3. I’m terrible at pretty much every sport involving a ball. 

I never played sports as a kid and always rebelled against them. As a result, I could not throw a football or kick a soccer ball to save my life. A golf ball is the only one I can manage – if you can even count that. But I love volleyball and I’m slowly improving my skills. Very slowly.

4. I do handstands on the street when I’ve had too much to drink (and when I haven’t). 

See the picture above – that’s me playing in Thailand. I love handstands. Especially on grass and beaches. They might be my single favorite physical activity. Anytime I see grass, I’m up on my hands walking around. And when I’ve had a few drinks, I’ve been known to go vertical on the sidewalk outside a bar, restaurant or club. I’m also pretty damn good at them (although Chelsea will tell you my form is terrible) and can walk for minutes on end.

5. I was a rebellious disaster of a child – and even saw a child psychologist a few times.

His name was Barum and he tried to get me to throw a Nerf basketball with him just like you see in the movies (bad idea – read about me and ball sports). Today my parents will tell you that I was just a little “mischievous,” but I put them through way more hell than any parents should have to deal with. We still can’t figure out what caused me to turn around, but it happened sometime between 8th grade and high school. Maybe it was that two-week Outward Bound backpacking adventure I was sent on.

6. I love pastel-colored clothing. My favorite pants are white, pink and mint julep green.

And I’m obsessed with linen. It’s the ultimate leisure clothing. I’m wearing all linen in the handstand picture at the top. And here’s a little sample from “Pink Out” – a rosé wine tasting event Chelsea and I attend in SF each year. They encourage everyone to wear pink. My Pink Panthers made for the perfect pant – I know they look white but they are very light pink micro-corduroys. Btw, if anyone else likes a little flare, you gotta check out Bonobos online men’s clothing. Their stuff is so fun – been buying from Andy and his team since they were selling out of their apartment.

I love pink Bonobos pants

Yes, I am wearing more pink than my wife…

7. I am a terrible speller. Like awful. 

In fact, I just tried to look up how to spell “mischievous” and Google couldn’t even figure out what I was looking for because I was spelling it with a “G”. Thank God for spell check and Cherilyn, my editor!

8. I’m sometimes not as good of a manager as I want to be or as fair to the people I work with as I’d like, but I’m learning.

I always thought I’d run a business with me as the only employee. I wanted to keep it simple. But in the past year, I’ve realized how crucial the right talented people are to the future of the Live Your Legend movement. I’m so grateful to have the team I do, but I know I have so much to learn about management. It’s a constant evolution and I thank them for being patient.

9. I can’t stand seeing people waste their potential.

I don’t think there’s anything more frustrating. I so badly want to do something to help them, but I know it’s useless until someone decides they want to operate on a higher level. At times this leads to some uncomfortable, intense and heated conversations.

10. I can be really stubborn. 

Goes with the point above. When I’m dead set on a idea, it’s very hard for me to get myself to let up. This can be frustrating for those close to me.

11. My wife Chelsea is far and away the best thing that’s ever happened to my life. 

I managed to marry up in a such a huge way. She makes everything better. She’s unbelievably selfless and loving. She’s obsessed with cooking delicious vegan food (check out her Creamy Vegan Roasted Tomato and Eggplant Sauce Pasta or her Peanut Butter & Chia Jam Thumbprint Cookies on her site Food-Life Balance). She’s my best friend and we seriously have the most amazing life together. She’s also my Chief Balance Officer. Her calm, balance and chill approach to life is the best medicine in the world. Our wedding was easily the best day of my life. Here’s a short trailer from the big day…

Don’t see a video? Click here

12. I’m obsessed with eating and often eat when I’m not hungry.

I read and learn a ton about food, nutrition, health and overall well-being, and most days I eat a super healthy plant-based vegan diet. But from time to time I still find myself emotional eating and consuming sweets and things I know don’t belong in my body. It feels like I can’t stop eating because I love putting food in my mouth. Seriously – I think I have an issue with it. Maybe that’s why I’m so crazy about fitness and eating only plants. It’s pretty tough to O.D. on salad.

Chelsea and I also happen to have food-focused lives. She cooks amazing meals for her recipe blog The Simple Kitchen (which is a pretty nice side benefit for me, the taste-tester..). And when we travel, it’s not uncommon for us to be talking about dinner while we’re having lunch. When I travel and go to events, what’s going to be eaten is often front of mind. I’m actually a bit concerned that eventually it’s going to catch up with me…

13. I fail often and I failed for four years straight. 

The blog I ran before Live Your Legend was called Reading For Your Success. I wrote personal development book reviews for four years straight, while it grew by exactly zero percent. The only real people paying attention were Chelsea and my mom and dad. It was very frustrating, but it allowed me to find my voice. And for Live Your Legend to become what it is today. I fail at things all the time. Earlier this year I thought I could start a stand-up desk business with a friend “on the side.” Who was I kidding? I’ve come to embrace failure as part of the never ending life of experiments and learning. Now it’s kinda fun.

14. I’m scared that I’ll always live in the shadow of my parents’ success. 

I was fortunate to be born into a incredibly supportive and close family. My parents are some of my best friends and mentors in the world. My father was also quite successful in his business endeavors. For years I tried to follow in his footsteps, which was brutally hard on me. It wasn’t until I found my own path with Live Your Legend that I really felt like I could be myself.

But to this day, I know there are lots of people who think things like, “Oh sure, Scott’s successful because he had that easy start from his family.” A number of them have even said it straight to my face. It used to hurt me. And it’s very possible that no matter what I build or achieve, that some people will always say things like that. The difference now is that I know that’s not in my control, and I no longer care about what they think.

I built Live Your Legend from scratch, over the past 7+ years with zero outside investment (it took me $67 to start) and no special family connections. I knew nobody in the space when I started. I’m damn proud of what it’s turned into. People can say that I was one of the “lucky ones,” but I’ve worked my face off to build what I’ve built. The only family help I’ve had is their undying encouragement and some really fun brainstorming with dad – my Chief Strategist. That’s been priceless. Here’s a sneak peak a the possible Dinsmore family Christmas card candidate for this year (a tad over-staged I know, and yes, that’s me wearing white pants and linen…)

The wonderful Dinsmore family

15. Sometimes I feel like email runs my life.

For the life of me, I cannot seem to get ahead of my email box. My personal email has 51 unread emails in it, and it’s Monday morning (it had nearly zero yesterday). Not to mention LYL email that has well over 200 – but thankfully my team does an awesome job of handling the LYL part. I’ve tried so many things to handle email in a smoother way, but it’s been this crazy beast. I’m getting better, but I’m still not at all proud of how much time I spend buried in Gmail.

16. Sometimes my inspiring friends make me feel small. 

There is no more powerful life hack in the history of the world than hanging around the people doing the things and living the lives you dream of living. I’m grateful for the friends and mentors I hang with on a daily basis. And while for the most part they inspire possibility, sometimes being around them and hearing all their big progress and projects makes me feel small. Like I should be doing more. Continuing to focus on my internal yardstick has helped a lot.

17. I have a very limiting belief that if I don’t over prepare, I will fail.

I constantly over prepare. I rehearsed my TEDx talk for 12 hours straight the day before (not to mention the days prior). I so wish I could have just spent three hours and have been okay with it, but I just can’t get myself to do that. Most articles I write take over seven hours, despite trying to to keep them to a couple hours every single week. It’s been a blessing and a curse.

18. I’m more extreme with things than I’d like to be. And sometimes it gets me hurt.  

This is something my parents and Chelsea are always a little concerned about. I like extremes. Or better put – I really only seem to be able to operate on extremes. I only have two levels: Absolutely everything I have, or nothing at all. It’s exhausting. It’s pour 400 hours into building a product or spend zero. Run an ultra marathon or stick to walking. Eat fried foods and sweets or do nothing but veggies. Instead of doing a casual CrossFit class, I push myself to win. Last year that resulted in an impinged shoulder and partially torn hamstring. It took me nine months to recover. I’d love to be more casual with some of the things I do.

19. I don’t always do the things I’m supposed to do. 

I read and learn a ton about health, performance and optimal living. And just because I know how to live a strong, healthy, powerful life doesn’t mean I do all of it. I screw up all the time.

19b. I have been arrested in high school and put in jail for the day – but the charges were later dropped…

I’m adding this late and have no idea how I left it out because it was a hell of a story!

I grew up in an outdoors family and some friends and I were out at a private property of our families and shooting shotguns at tin cans and targets when the police showed up in full force, guns drawn (3 cars and 5 men) and yelling through a megaphone ,”Put your weapons down, put your hands up and slowly walk towards the gate.” They thought there was some type of a shoot out going on. It was like we were in a movie and it was terrifying. They took me to jail, and my friends had to get a $10k bail bond to bail me out. It took like 12 hours. Longest 12 hours ever…

All the charges were later dropped since we were indeed on private property, well outside of city limits and not actually causing any trouble, but it was a total mess. Thanks for reminding me in the comments below Paul. 🙂

20. I love Brazilian Jiu-Jitsu. And I get my ass kicked a lot.

I don’t think there’s anything that makes me feel more alive. I was on a competition team for nearly six years. I actually did pretty well, too. But I stopped because I didn’t want to deal with the injuries. Three weeks ago I decided to drop into an academy near my house. It was the most invigorating two hours I can remember having. The next week I got a bruised rib in class and I haven’t been back since. If I could only dial down the intensity to 50%…

21. I have pretty much zero rhythm, but I’m not afraid to (break) dance. And sometimes my pants split open…

As a child, my friends always made fun of me for looking like a scarecrow on a dance floor. Then I moved to Spain and realized no one knew I was embarrassed to bust a move. So I told everyone that I loved to dance. They believed me and actually thought I was decent. Now Chelsea and I love to get down. In fact at a wedding last weekend I danced so hard that the butt of my pants blew wide open – and I didn’t even realize until I got home. Now that’s how you dance your ass off (here’s proof).

Sometimes we even watch YouTube videos to learn the latest music video moves – like how to shuffle. We even took a series of breakdancing classes earlier this year. It wasn’t pretty, but what the hell – here’s a short video of me in action…

Don’t see a video? Click here

22. I can sing every word to the musicals RENT and Wicked. 

I’ve seen RENT about a dozen times. I freaking love it. Wicked is the same. In fact, I like a ton of musicals. There are a few tracks from each on my “Inspire Me” mix on my iPhone. And on special party nights I’ve been known to belt it out with friends at the top of our lungs during the wee hours of the morning.

23. I can do the splits. 

This is hard for a guy to explain, but I’ve always been kind of obsessed with flexibility. One time it lead to a slight muscle tear. My wife being a yoga teacher doesn’t hurt, or I guess it did that one time ;). Yoga teaches often tell me “you’re very open for a guy.” I take that with pride.

24. I’ve done some things I’d never do again – like running with the bulls.

We started from the most aggressive point on the course – right at “dead man’s corner” where we thought we’d have the best chance of running into the arena with the bulls. It worked. It was also the single highest moment of panic of my life. I would not have done it if I knew the type of chaos involved. But I’m happy to have the story to tell…

Running with the bulls

25. I used to be a tour guide throughout Spain, Morocco and Portugal.

When I lived in Sevilla, I was a tour guide on the weekends for my friends Eric and Jorge’s tour business, DiscoverSevilla. I can’t tell you the feeling of power I felt from holding a silly clipboard at the front of a tour bus.

26. I wish I was closer with my childhood and high school friends. 

I had some very close and fun friendships as I was growing up. And while some of them are still in my life in a big way, there are lot of those relationships that I really miss. It’s just that in the past years as I’ve learned more about myself and pursued a path true to me, I’ve had less and less in common with them. It’s driven us apart. I wish it hadn’t.

27. I like feeding ducks.

There’s a pond near my house at the Palace of Fine Arts. It’s so mellow and tranquil to head down there with some bread crumbs. I wish I did it way more often.

28. I love rosemary.

Every morning I go on a walk or run and pick a sprig from the same bush. Every time I pass a plant, I have to pick some. It immediately calms me down.

29. I have the musical tastes of a 13-year-old girl.

And I’m proud of it. Last month I was in the 3rd row at a Taylor Swift concert. It was freakin’ awesome. Three years ago I took my wife and parents to our first Taylor concert, and dad sent me an email the next day saying it was the best performance of his life. And between you and me, I’m trying to get Taylor to do a short Living Legends interview for our audience – so if you happen to know her, let me know!

I also have Taylor Swift, Miley Cyrus and Christina Aguilera music videos on my iPhone and on my “Inspire Me” mix. In fact Party in the USA was the last song played at my wedding.

I really enjoy the music, but I also love how most musicians are so fully living their dreams. And some, like Taylor, still take their job as role model very seriously.

30. I’m really scared of getting old.

I turned 31 this year, and it’s been kind of tough realizing that I’m not a total beginner anymore. That adds a lot of pressure. I’m also really scared of the people older than me – especially my parents – eventually dying. I honestly don’t know what I’d do without them right now.

31. I’m kinda terrified of public speaking – at least the build up to it. And a lot of things make me nervous. 

But I absolutely love it. Nothing feels more rewarding than stepping on a stage and doing my best to address and inspire a crowd. I love the feeling I get from being on stage, but the build up is absolutely brutal. Lately I’ve gotten a better handle on it, but the stress and anxiety that’s led up to some of my past few talks has been no fun at all. I’m learning how to cover the details without creating a pile of stress.

32. I feel rushed way more often than I’d like. 

I’m not sure why, but so often I feel like I don’t have enough time to do the things I need to do. Even though I plan my week very carefully and do get important things done, I almost always feel like I haven’t done all I wanted to do. It’s really unsettling. And the crazy thing is that I’ll sometimes feel rushed even when I sit down early Monday morning with 10 hours ahead to spend time on projects. It makes no sense and it’s something that I’m constantly working to improve, which brings me to…

33. I am constantly battling and dealing with stress – and it’s brutal. 

Anxiety too. With all that’s happened in the past few years, I’ve begun to feel intense pressure to deliver on a never-ending rising standard. It’s exhausting. And the on-and-off stress and anxiety that sometimes come with it has been incredibly hard to deal with. And massively frustrating. On the outside (and much of the inside) I have all I could ever ask for. A family, wife and friends who love me. A business and purpose I deeply believe in that more than covers my financial needs. An incredibly healthy body and the freedom to do things I want to do with the people I want to do them with when I want to do them. Yet for the past six months or so, there has been this level of stress that’s been taking a lot of the fun out of things and I just can’t get my head around it.

The last few weeks have actually been the most stress free I’ve had in months as I finally decided to draw a line in the sand and do something about it. Last Friday, I spent four hours in the garden at Green Gulch Zen Center with my good friend Lissa Rankin. That investment was incredibly helpful, and while the stress is far from totally solved, I’m very confident that I’ll figure this out. It’s my top priority.

Update: After writing this, I got a lot more serious about finding a solution. I tried dozens and dozens of things and for the past three months the stress and anxiety have totally gone away. I think a lot was at play and I plan to write a full article on my Stress Management Campaign sometime soon.

34. I meditate for 20 minutes almost every morning.

I’ve been doing this since I took a Transcendental Meditation course a little over a year ago. It’s helped a lot and it’s one of the best steps I’m taking to calm the mind and soothe the stress. I’ve come to love my morning practice (most the time).  😉

35. I don’t know what I’m doing a lot of the time.

This business and movement has grown so fast that a lot of the time I don’t have a clue what to do next. I just do my best to surround myself with inspiring people who have been there and stay true to my beliefs and values. I wish I could say that I’m steering the ship, but honestly, I tend to just hold on tight to see where it takes me.

I have no idea how you’ll respond to this list.

I’m nervous writing this right now. Flat-out scared, in fact.

But as Jonathan Fields likes to say, that feeling in your body, that intensity is a sign that what you’re doing actually matters.

I hope he’s right.

And to be honest, that felt really really good to share with you all.

I hope you’ll continue to accept me for who I am. Because that’s the only person I’m willing to be for all of you.

And I hope you’ll hold yourself to the same standard.

Now please, join me and share something about yourself in the comments.

I’d rather not have to do this alone.

Here’s to being you and inspiring others to be them,


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