What Makes Chelsea Dinsmore Tick

In ‘What Makes You Tick’ I get the chance to pick the brains of some inspirational people from all walks of life, in the hope that by sharing ideas we can continue to progress, push our limits, and inspire each other.

Chelsea Dinsmore is the Chief Inspiration Officer of Live Your Legend, a community whose mission it is to change the world by helping people discover and do more meaningful work. Through their online platform, articles, and courses they offer people the chance to venture deeper into the process of discovery, and guide them in implementing these tools for their benefit, in life and career. 

Chelsea was kind enough to take the time out of her immensely busy schedule to answer some questions, and share her insights.

Would you say you are more introverted, or extroverted? 

You know what I find to be really interesting about this idea of introversion and extroversion, is I think I am an outgoing introvert, if that makes sense. We have a whole course in Live Your Legend focused on getting out in the world, which I think is very appealing to a lot of introverts because perhaps that’s something that they struggle with- connecting with other people. I don’t have that problem but I feel that my energy is replenished when I am on my own. I recharge my batteries when I’m alone, and that is something that we talk about as being a characteristic of an introvert. Do you do that in a room full of people or do you need to go off on your own. I kind of have a little duality about me, in that on the outside I may appear very extroverted but I think that I recharge on my own.

What are your hobbies/interests?

Well, travel is huge. I absolutely love it, I think it’s such a great way to open your eyes, and get yourself to experience and do things that you never otherwise would have. I’m big into yoga; physical fitness is very important for me too. I love yoga, I love hiking, and surfing. Anything which involves an ocean, I will be immersed in it. Aside from that, I also really love to cook. I haven’t been able to do quite as much of it as I’m used to since I’ve been on the road so much, but cooking is something that I really love to do; to create something from nothing is something that I really enjoy.

Describe your typical morning routine. (How do you prepare for the day ahead?)

I prefer to start my day with more of an active type of meditation; I like to start my day off with a burst of energy. So usually when I wake up I will take a few moments to take a few breaths, and think of a couple of things that I’m grateful for. I think it’s a really great way to start the day. I generally write those down.

And then, if I’m at home in San Francisco, I will throw on my favourite jams and I will jump on a trampoline. This is something that I’ve learned from Tony Robbins. I bring a jumprope with me everywhere I go when I travel, so I can do it when I’m on the road. I’m really in touch with music and so when I hear some of those songs that I love, and I’m jumping along to the music, it just is a really energetic way to get your day started. I have a Spotify playlist with all my favourite songs and I generally will just push shuffle, and start bouncing. Definitely not an average, normal morning routine that’s for sure.

There’s meant to be some real benefits to that point of zero gravity; when you are going up and down you reach a point where you are standing in stillness and it’s meant to be really good for your lymphatic system, so it’s more than just fun I guess. Supposedly there’s some science behind it, at least that’s what I’m telling myself.

And then I also take a cold shower, and I drink lemon water. So I guess I do have a routine, more of a routine than I thought.

Describe your perfect Sunday.

Gosh. Well it depends on where in the world I am. I do set boundaries for myself; when you run your own business it’s a very important thing to do. It’s very hard to mentally check out, so for me at least I try to physically and mentally check out from time to time. On Friday afternoon I will close my laptop, and generally I try and not do anything business related over the weekend unless I have to.

So a perfect Sunday for me would start off with something related to physical activity, oftentimes here in San Francisco that would include some sort of yoga. If I am out in the world or travelling I love to just wander until I get lost. Sometimes I will just put on a camelback and head out with no plan or intention, and I won’t end up coming home until hours later. So some physical activity for sure, and then rewarding it with some sort of nice meal would be awesome. I don’t nap great; I try to do that at the weekends when I can. So, a Sunday afternoon nap would be amazing. Then heading to dinner with some friends or family would be the perfect way to round off a Sunday, whether that’s heading out for a meal or me cooking, that would be lovely. Also, when I’m in San Francisco I love to go to the farmers market, but that’s not too often.

That would be an ideal Sunday for me.

I am happiest when…

Well, I am blissfully happy when I am on a plane. I know some people don’t like the idea of having to fly, but it is one of those feelings I love; that moment when I’m walking down the strip to get onto the plane, I literally feel like I am meant to be there, and it touches a deeper part of me. I think I love being in a place where there are no distractions.

I find it to be such a creative time for me, too. I write a lot when I’m on a plane. Even if I’m not doing that- if it’s just an hour flight for instance- there’s just something in my being that ignites when I’m getting on a plane. And I feel the same way when I’m in the ocean as it happens; I always say whether I’m in the sky or in the sea. Those are the two places where- on a deeper spiritual level- I feel most alive.

Do you have a guilty pleasure? 

I mean, it’s probably something food related. I love food, so maybe that in general is my guilty pleasure. But I tend to eat pretty healthy so I think that a guilty pleasure to me is just not caring and letting go; I don’t really like sweets too much though, so for me it’s more like, I don’t know. Well, I love Italy- the carbs, the pasta, the cheese and all of that- so that’s probably what it would be. Although I think maybe a guilty pleasure is something that you don’t partake in very often, and I definitely eat whatever I want. So aside from that, maybe weekend naps. That feels very luxurious to me, for sure.

What’s the best book you’ve read, and why?

Oh my gosh. One of the books that has really opened my eyes is one that I’m actually finishing right now. Interestingly enough, a year ago I would never have picked up a book with this title. It’s called Conversations with God. The thing that I think is so profound about it is, it zooms out so far on the outlook of humanity and why we are all here, and our purpose and how we are all inter-connected. It takes an alternative approach to some universal beliefs and things that we as humans are motivated and driven by, and things that we as a society immerse ourselves in. I’m the kind of person who doesn’t take anything as gospel; I like to look at the big picture and take bits that resonate with me. This book kind of flipped my view; I kind of like that big picture thinking in terms of why we are all here. That is really profound for me. It comes as a series, and I’m on Book Three right now.

But thinking of something that isn’t so present, to be honest it’s a question that leaves me stumped actually and I don’t know why. Anything spirituality based I guess. Of course The Alchemist, I’ve read that a number of times and it sort of was a huge motive for what started Live Your Legend. That’s one that I would refer to over and over again.

What is your passion? 

Interestingly enough I think with regard to this idea of passion, and I talk about this very openly on Live Your Legend, discovering it is an ongoing process. I think the better you know yourself, the more you find yourself rediscovering what it is you are passionate about. Ten years ago for example, I had a passion of teaching yoga, which evolved and transferred over to a passion of cooking, and giving my life’s circumstances changing so much, I am currently in the process off rediscovering what I want my mark on the world to be.

I definitely know from working within the Live Your Legend community, I am passionate about reaching the younger generation. We are working towards reaching younger people and graduates; it’s such a profound time to get ideas in your head. I started the process of self-discovery at around 25, which I think is quite young in comparison to most, but I often imagine if in high school someone would have said to me, “Chelsea, you don’t have to walk this standard path. You can do what lights you up. You don’t need to get a job, just to have a job.” I think it would have drastically altered my trajectory at a much earlier age, so I’m deeply passionate about getting people at a younger age on this path of self-discovery, finding out who they are and what they want out of life.

I’m also passionate about using your strengths and talents to give back. We host a world party at Live Your Legend where communities around the world get together every year; the next one will be focused on active community service. So we’ve been asking people this month to start to think of a need in their community; like going to a soup kitchen or making treats for homeless people; just to identify a need in their community, and at the beginning of next year we will get together on the same day and provide an active community service. That’s something I’m very passionate about. I always told Scott in the past, that if he ever had a foundation, I would work for Live Your Legend. So the idea that we can all give back, even in some small way, drives me. I believe that it’s our responsibility to leave the world a small bit better every day that we’re in it.

How do you measure success? (What does success mean to you?)

To me it’s something that’s more of a culmination of small moments rather than, you know, some big accomplishment. I personally feel successful when I have taken the time to know who I am, how I want to spend my time, and then use that in a way to give back. That can unfold in many different ways, for example just me walking into a room full of energy, and sharing a smile, or other days it may be that I’m standing on a stage giving a speech, or writing for Live Your Legend. I think success to me, is acting in alignment with who you are, and spending that time to make a greater impact.

Who had the most influence on you at a young age, and why?

Scott obviously had a huge influence on me, because we began dating very young, and so we were going through that early 20’s stage of figuring things out together. It’s kind of an interesting aspect of my personality, in that I’m sort of a rule follower, although I’m very curious at the same time. I haven’t always done the standard thing. I always find myself questioning things. He really opened my eyes, and helped me realise that it didn’t have to be one way, so yes, he had a huge influence on me at that young age.

I also went to a Tony Robbins event when I was really young, I was 24 or 25. Some people go to an event like that and they claim that their whole life changes in an instant, but it wasn’t the experience that I had as I recall. I do remember though, that it profoundly changed the way that I understood just how much responsibility I had for my own life, if that makes sense. I remember coming away with the realisation that it’s in my control how I respond to things. Prior to that event, I think I lived a very reactionary life; for instance someone does something to me- I get mad. I realised after that event that we really have a lot of control over how we choose to respond to the events and the people in our life. I would say that was a big influence, and I’ve done a lot of work since with Tony Robbins, so he’s been a huge mentor of mine for sure.

What was the most significant learning experience you can recall having?

I think the thing that stripped me down to the rawest place was definitely Scott’s passing. I was at a crossroads in the sense that I had to decide am I going to show up, or am I going to give up; I was stripped to my core. I think that oftentimes the most extraordinary situations also have the opportunity to create the most extraordinary results. The amount of growth that I have experienced, personally and professionally over the last year, I mean sometimes I look back and I think how has it only been a year. How have I done all of this in a year, so I think that was huge.

Prior to that, not getting into medical school. It was a time where I had to sit down and really think things through. The way I thought my life was going to play out, and where I saw myself, was severely challenged in the sense that I always thought that I was going to go to medical school and become a doctor, and when I didn’t get in it was the first time really in my life, where I sat down and said: “Ok. What do you want out of life? That dream is no longer a reality, so what do you want?”

Those are the moments where you actually sit down with yourself and ask questions of yourself. Those moments create tremendous growth opportunities, that challenge you in a good way because they create results that cause you to grow and become a better version of yourself.

How do you deal with adversity or self-doubt?

I’m extremely curious, as I said. I think emotions and discomfort and things like that are really a guide for us, so instead of running away from these negative emotions I get super curious. If I’m feeling empty, or unfulfilled, or lonely or whatever it may be, I get curious. I think OK, this is presenting itself but, what else is going on. Why do I feel this way? What  triggered it?  What’s the story that I’m telling myself that’s making me feel this way? I just get very curious and oftentimes I find it helps to distill things down into something that’s a lot more simple. Like, we take complex situations, and get lost in the complexities sometimes, but I think when you break it down you realise that you’re just looking to meet one of your fundamental human needs of connection, or whatever it may be, and there might be a more resourceful way. I think being curious and asking questions of myself in these times, has helped me tremendously. In the moment of course, it’s not always easy because I think that curiosity sometimes makes you look at parts of yourself that you wish were a little different, but I also think that when you do that you are facing a part of yourself that you may realise might need some work. So curiosity definitely helps me in these moments.

What are some moments to remember or defining moments from doing what you do? 

I mean, I’m in a constant state of awe. To me, it’s the messages and the emails that I receive when someone reaches out and says something like, “Chelsea, I listened to your talk that you gave at WDS”. I’ve had people say that they were in grief for ten years and after listening to my talk, they realised what a waste it’s been. Or, I had a young girl reach out after giving a talk at her high school recently, and she wrote me a message and said, “Chelsea, I was so nervous. I listened to your talk before I gave mine.” She said that it helped her a great deal. She even quoted me at the end, I mean I’m getting teary-eyed even thinking about it. It’s just unbelievable to me, to think that by just sharing who I am, it helps people. Those are the moments to me that take my breath away. Moments where someone reaches out and tells you that something that you did or said, or wrote, made them think or act differently. I just am still in awe that that’s even possible. Those are the moments that matter the most to me.

What advice would you give to the younger generation, who may find themselves at a crossroads in life, unsure of what path to pursue?

I gave a talk at a university in April, which was about connecting. I used that lead in question of, What do you want to be when you grow up? Then at the end, I circled back to that question and I encouraged everyone to ask themselves a different form of that question, one of, Who do you want to be?

We are not defined by what we do, we are defined by who we are. I think so many people put so much emphasis on career, and it’s not surprising considering this is what we’re taught to do in society. We define ourselves based on our career; I’m a lawyer, I’m a doctor, I’m a this, I’m a that. I’m hoping that that needle is shifting, that we can start to define ourselves in different ways. I think it’s important to really think about the kind of person you want to be. For some people it is to be a mother, and they are meant to be on this planet to be a mom to their kids, and they know that from a young age, but then they pursue a path that is different because they think they’re supposed to.

So it’s really just a matter of asking yourself, who do you want to be? And, I think that starts with knowing who you are. Also, I would say to let go of the needing to know- that need to know how it’s all going to unfold- let go of that because you’ll never know. The only things we have control over in life are how we show up in the world, so as long as you’re continuing to show up in a place that’s in alignment with who you are, I think the universe has a very interesting way of helping you along the path, in ways that sometimes seem that they don’t make any sense, but I think that the more that you can live from that aligned place, and allow things to unfold as they’re meant to and to manifest as they are meant to, it ends up not only looking how you thought it would, but it allows you to really see the beauty in the journey as it unfolds, instead of being disappointed if it doesn’t go a certain way.

So getting to know yourself, realising and defining who you want to be and what you want your life to look like based on your values, and then letting go and enjoying the ride. To me, that’s how you will find yourself living a beautiful life. Every day, not just in the big moments!

You can follow Live Your Legend on FacebookTwitter and Instagram, and you can check out Chelsea’s keynote speech at this year’s World Domination Summit. You can also check out the TEDx talk given by Live Your Legend founder Scott Dinsmore, entitled How to Find & Do Work You Love, which has been viewed over 7,000,000 times and was listed as one of the Top 15 Ted Talks of 2015.