1988 - Williston, North Dakota
I rock my first business idea.
Most children set up lemonade stands to make a little cash flow. Not this kid. As I assessed the resources around me in my North Dakota garden, I saw an abundance of rocks. So I set to work setting up shop, creating a system for cleaning my rocks, and wheeling and dealing them with the neighbors. It wasn’t about what I said ("Hi, want to buy this rock?"). It was about how I was showing up and who I was being (a very convincing, passionate five-year-old).
When you are really connected to what you want, people can feel it. That is your power.
Hello, from five-year-old me!
1997 - Casper, Wyoming
I adopt a rat and name him Paco.
While most most people look back on middle school with horror, I feel the opposite. I was busy rocking my JNCO jeans and Doc Martens, being on on the ski team, going to Latin and math competitions, and hanging out with my pet rat, Paco. My mother was the first person that had me see anything was possible and she supported and embraced all of my unique interests. Like any normal middle schooler, I do remember caring what other people thought about my choices, but I didn't let that impact the choices I made.
It's okay to care what other people think, but do not let it stop you from going after the things that you want.
Paco and I were truly a package deal.
2005 - Greenville, South Carolina
I quit the TV station and leave behind the career I thought I was supposed to have.
In high school, I dreamed of being a TV news anchor. Once I got to college, I realized that editing TV is HARD. When I was honest with myself, I was not willing to build a TV career by starting as a one-woman show in a small market in a place like Kansas, and editing and creating all of my content.
It was a terrible feeling to realize that what I thought I wanted was not what I actually wanted AND it was freeing to leave behind what I knew wouldn't be right for me.
You get to decide in every moment what it is that you want. It can change. Trust yourself enough to choose, take action and change course. You know.
My alma mater is consistently rated top most beautiful campuses in America, so that helped.
2007 - New York, New York
I move to NYC and live on $35,000 a year.
"Can I afford to live in New York on $35,000 a year?" was the first question I asked my New York uncle when I got the job. After a moment of hesitation, he said, "If anyone can do it, it's you!" I packed my bags, and got busy creating my ideal New York life.
Had I stopped to consider all of the difficulties I’d face in moving to New York (budgets! adjusting to crazy New Yorkers! cockroaches and mice! terrible roommates! heartbreak central! confusing buses!), I might have paused to reconsider. The challenges I could have run into didn't stop me because of all of the possibility around me.
Trying to figure out every single detail prior to saying "Yes" to what you deeply desire will often get in the way of getting closer to it.
Oh, just me and my roomies being featured in
an article in the New York Times, for our apartment-hunting skills no less.
2008 - New York, New York
I become a first year teacher in the New York public school system. It's hard.
My second year in New York, I went from waltzing into a "desk job" as a recruiter to reporting to the rug everyday with my kids. Here's the kicker: I didn't have training in teaching. Most of the time, I had no idea what I was doing. But I showed up and failed fast. By year two, my classroom management abilities were a thousand times improved. It was here that I learned how to hold the balance between humble and badass.
If you want something, be willing to show up for it every single day. Even when you're not great at it.
As you can see, I (Dora the Explorer) went to great lengths to get my kids excited about learning and hold their attention.
2013 - Small, random cities across the US
I'm a miserable traveling consultant.
I thought I would love the consultant life. Hotels! Airplanes! Super important client meetings! Adventure! I was wrong. I had to leave the city I loved, New York, for months at a time, and make a life in a hotel room in whatever city I was needed.
After I allowed myself to grieve what I thought this career would be and wasn’t, I chose to embrace my new life fully. I put myself out there - I asked locals to dinner, joined an amazing spinning community in Nebraska, and was lucky enough to have families who basically adopted me into their lives. I ended up creating a truly magical experience on the road.
Your happiness is your responsibility. The things that suck can move you closer to understanding what you do want - if you allow it.
Me enjoying life in the midwest
2015 - New York, New York
I score a job at my dream company.
I really, really wanted to work at Linkedin. Here's the kicker: I got rejected multiple times before getting hired. I'd had my eye on the company for years. Because I wanted a job there so badly, and because I beleived I was worthy of it, I advocated for myself and my value relentlessly. I created personal connections at the company. I asked people in the field for help. I didn't let a bunch of "No"s talk me down from what I wanted.
Remember what you want, even when the world tries to tell you otherwise. Keep going.
Selfie or it didn't happen.
2015 - New York, New York
I admit that I want to be a coach.
I had tossed around the idea of being a coach for several years, but I let excuses ("Is this practical?" and "Do I have time for this?") get in the way. When I got to Linkedin, my boss asked me what I saw for the future of my career. I told him I thought I wanted to "be a coach one day". He responded with, "By when?" Talk about a confronting question. That was when I realized that there was nothing in the way of me doing this. I declared in that conversation that I would find a program, and was enrolled in one by September.
Now is the time to do the thing. You don't have to wait.
The incredible people I spent an entire weekend a month for a year with, doing deep transormational work together (in a hotel conference room)
2015 - El Chaltén, Argentina
I complete a serious hike without realizing just how serious it is.
Patagonia logo level serious. It was not until after my friend and I had already finished the 18 mile trek that we realized how intense it was. Had I known it was 18 miles instead of 10 miles, I might have allowed my brain to talk me out of it.
Just start. Take a buddy. See how far you get.
Casual 18-mile trek, no big deal.
Summer of 2016 - New York, New York
I believe that I can be an entrepreneur.
For the first year of my business, I related to coaching as my "side hustle." I fit clients in when I could - before work, after work, during lunch, you name it. I didn't have a vision of myself being able to be a successful entrpreneur.
I'll never forget the day it all clicked for me. I was sitting on the 22nd floor of the Empire State Building talking to my coach after work. She asked me how things were at Linkedin. I said, "fine," and quickly moved onto another topic. She paused me and said "Fine?" That's when it all hit me. A job that was once my dream job had turned into a distraction in the way of me going after what I really wanted - deeply impacting human lives full-time. In that moment, I decided to take on the belief that I could have my own business and I created a plan to have that within six months.
What's your version of "I could never be THAT"? There's probably some gold underneath there worth taking a look at.
Coach Cailin Version 1.0 at her first business photoshoot! Cute, right?
Winter of 2017 - New York, New York
I quit my dream job.
I remember asking my mentor at the time, "Who leaves a job like this?" He responded, "People like you do." What really made the difference for me was having people remind me over and over again of who I was and what I said I wanted. I was so paralyzed in writing my resignation letter that I asked a friend to write it for me and put it into a PDF six weeks in advance to fully commit to my end date. I also told my friend that I would give him $10,000 if I didn't follow through with my plan. This was a huge process for me in letting people support me during a big transition and putting structures in place to make a big leap. I could not have done it alone.
Take exquisite care of yourself, especially when you're upleveling to the next expression of success in your life. Everything inside of you will want to slow it down and back out! Ask the people in your corner to support you extra during these times.
Do we think this photo is appropriate? Caption?
2018 - Los Angeles, California
I move to LA. Because I can.
I'd lived in New York City for 11 years and 8 of those years I lived alone, which felt like an accomplishment at the time. When it came time to renew the lease of my one bedroom apartment in Brooklyn, I was avoiding it because I knew deep down I didn't want to keep living alone. I had a desire to live with an amazing community of friends but wasn't sure how I could create that in New York. A few days after I told my landlord I was moving out (with no plan), a good friend in LA called me. She asked if I wanted to create a community house with her in a big mansion in LA! I let go of all the stories I had about being crazy for moving across the country to build a community house. I packed my bags and was in LA a month later.
Everything is figureoutable. The first step is to admit to yourself what you want. Spend less time complicating things and more time staying out of your own damn way so you can have the thing.
Happily ajusting to the fact that I have palm trees in my backyard.