Lessons Learned on the Road to Making My Dreams Come True

This past week, one of my dreams – to teach a Vivid & Brave workshop – came true at the Inspire 2014 Photo Retreat. And let me tell you:

It wasn’t easy.

Travelling from Alberta to Massachusetts is a challenge at the best of the times. There are no direct flights so it makes for a very long travel day. When I booked my flight into Hartford (Connecticut, close to the conference location), I had a 56 minute layover at O’Hare. Having made a mad dash through O’Hare before, I was super worried about the very short layover, but little did I know it would end up being the least of my concerns.

I left my house at 4:30 am last Sunday morning. It was COLD. Bitterly cold. Parked my car at the Park n Jet, got on the shuttle, checked in and cleared customs and security without a hitch. I even had a great conversation with the customs agent, which doesn’t happen often. Or plane was late being towed to the gate, but United agents assured us we would all be fine. The minutes ticked by. An hour after we were to board, we finally got on the plane. And then they realized the plane had a frozen waterline. No problem, they said. We’ll just turn the heat up. It might get a little warm in here. An hour later, we were still slowly cooking inside our metal box. They encouraged us to get off the plane and go find food. It was 10am by now, and line ups at every single food vendor were 20 people deep. Ten minutes later, they called us back, most of us reluctantly giving up a place in line that was still woefully too far away to place an order. We reboarded, got settled, and then waited 40 more minutes while the plane was de-iced. Three hours late, we were finally airborne.

At O’Hare, they had bumped me to the next available flight – at 7pm. I was panicked. My carefully orchestrated plans – arrive in Hartford at 4 pm, have a friend drive me to the conference in time for dinner with those who arrived on Sunday, were completely shot. Now I’d land in Connecticut at 10 pm – too late for my friend to make a round trip of that length when he had to work in the morning. I was deliriously tired. Phone calls on my phone were costing me a bank breaking $1.50/minute. Thankfully, the friend who was going to act as my chauffeur came to the rescue, arranging a back up plan for me to still make it to the conference in time for my class. We arrived at his house after midnight and I collapsed into bed. In the morning, I rented a car with GPS, hit a Starbucks and was on my way.

Twenty seven hours after I walked out of my house, I arrived at the conference hotel. Our class started at 1. In a word, it was AMAZING. It was exactly what I’d dreamed of, come to life, with my best friend at my side. It doesn’t get much better than that. Those three days were some of the most inspiring, soul nurturing days of my life. I loved every second of it.

On Wednesday, I got the call that my flight home had been cancelled. The GPS in my rental car wouldn’t turn on for 2o (tear and curse word filled) minutes.  In the end, I’d finally make it through my front door on a similar timeline to the one at the front end of my trip – 25 hours after I should have arrived.  This entire experience has led me to this list –

Lessons learned on the road to making my dreams come true:

  1. The road won’t be easy but it will be worth it. No path to your dreams coming true will be simple, easy or straightforward. It just won’t. But when you’re done stumbling, tripping and getting lost on the sideroads, it will have been completely worth it.
  2. Be flexible and adaptable. You can make all the plans in the world and you should plan. But be ready to change those plans, sometimes more than once. Have a back up plan in place. Have TWO back up plans in place. You will need them.
  3. Ask for help when you need it. You’re going to need it. I promise you will. Get well versed in asking for help. Get clear on the help you need and ask for it.
  4. Realize you aren’t alone. You’re going to feel alone. But you aren’t. There are so many people struggling through the same hard roads that you are. Everyone is trying to get to where they’re going, and everyone feels alone. Reach out to the people around you, and see how you can help each other.  Be honest about how hard this is.
  5. You can handle more than you think you can. Five years ago, this much chaos in the middle of my plans would have sent me into a tail spin. Someone would have found me curled up in a ball in a corner of O’Hare, crying for my mom. I did a lot of things I’d never done before on this trip – drove between states I’d never been in, in the winter, in a rental car. Dealt with majorly delayed and cancelled flights. Spoke in front of a room of people on very little sleep.
  6. Look for silver linings. Always, always be on the lookout for the silver lining in the struggle. There is almost always something waiting for you to discover it – a new friend, a beautiful landscape you’d never have seen if you hadn’t gotten there at that exact moment, or just this: You’re doing something that not everyone gets to do. Not everyone gets to chase down a dream. Revel in it.
  7.  The hustle never stops. Very few big dreams stop the moment you achieve them. Most grow or change, and you find yourself headed down the road again. Stop long enough in the moment to really soak it in, and then get ready to do the hard work again. And again, and again.

Stephanie Ostermann

I’m the sort of girl who you meet for coffee and end up pouring your entire heart out to. The friend you come to when you need someone to call it straight. No bullshit. No extras. Just truth.

I’m a communicator. That’s a PC way of saying I like to talk, but I also spend a lot of my time listening, and over the years, I’ve developed a sense for subtext – how one or two words can change your entire message, what people are really trying to say and how to weave the varied layers of your story into one cohesive brand message that your clients fall in love with.

When I'm not acting as editor in chief for Vivid & Brave, you can find me geeking out over words here.

Latest posts by Stephanie Ostermann (see all)