Reflections on Dreams

Yesterday, I spent the day skiing with coworkers… and our CEO. We had met before, when I was persistent about asking him questions about the future of our firm (say what you will about me, but I’m not afraid to speak up!), and he remembered me well. He turned out to be an excellent skier, but was one of the most vocal about not letting me go off on my own – he was adamant that we should all stick together as a team. So nice to see that kind of team commitment from the top levels!

I ended up riding the lifts with him a few times, and when it was just the two of us on a double chair, we got into some really good discussions. We had been talking about the future of the firm, and then transitioned into a discussion about what I wanted out of my career and where I saw myself years down the line. We talked about progressing through the levels and what I could expect in the years to come, but then he asked something much more broad: what was my goal for life in general.

Let me tell you, that is a tough question! Especially when asked by someone you want to impress (like the CEO of your firm). My first response was that I wanted to have a family and find a way to maintain a good work-life balance – that I wanted to find a job where I could be successful at work without sacrificing my personal life too much. However, to bring it into the nearer term, I asserted that my short term goal was to take advantage of as many opportunities as possible, while I’m not tied down, and live my life with as few regrets as possible.

After discussing my marathons for a while, we then got onto the topic of travel. The CEO’s family was going to be moving to a South American country for six months, and his kids were going to be attending school there in Spanish. I was so impressed and jealous that they were going to get that kind of experience at such a young age! I’d say that one of my biggest regrets so far in life is how I squandered the time I spent studying in Copenhagen when I was in college. I didn’t take advantage of the experience like I should have… but my CEO pointed out that the fact that I already recognized that and learned from it means it wasn’t a wasted experience at all. And he’s right! Look at all the travel I’ve completed in the past few months on my own, and how I’ve been taking advantage of as many opportunities as possible. When I mentioned that I was taking off this week for St. Maarten, he cheered me on and encouraged me, saying it seemed like I was definitely on the right path to achieving my aforementioned goal.

We then got into a discussion about how much travel can enrich your life and change your viewpoints, and how we agree that more people need to realize this and prioritize travel experiences over material luxuries. He told me that if he had one piece of advice to give me, it was to take a lot of risks now and be spontaneous. This made a lot of sense to me. We all understand that your risk level in your investment portfolios should correspond to your age (i.e., older people should be more risk averse), and we accept that as fact… yet somehow, young people tend to rebel at the idea of making mistakes and following an imperfect path. We want it all figured out and we want to predict the future – but we can’t always do that. My CEO said that he had been given the same advice when he was younger, and didn’t take advantage of it, and we tried to understand why it is that younger generations can never seem to accept the advice of older generations. We all think that we know better, but we end up following in the steps of those who came before us, and not necessarily advancing.

All in all, we had a pretty good heart to heart on the lift rides we took, and I was so glad to get to go on the trip and spend some quality time with our CEO. The discussion we had is still resonating with me now, and I hope that I am one of the lucky few who is able to take the advice that I’m tempted to rebel against. I am a total Type A planner, so it’s hard for me to swallow that I can’t just make a life plan and make it happen. I tweeted yesterday about my favorite quote, “if you can dream it, you can do it.” But maybe we need to focus less on the dreaming and more on just doing, doing, doing… and seeing what dreams are the result.

Are you good at accepting advice? What one piece of “life advice” would you most want to share with those younger than you?


  1. I’m embarrassed to tell you that I’m just now finding out about your 50 States thing. AWESOME!

  2. Best advice I ever received came from the book, the Monk and the Riddle by Randy Komisar. It’s more of a business book, not one of the self-help books. But he talks about how too many people take jobs that are miserable so that they can retire and then do what they want (the deferred life plan as he calls it) when we should opt for the whole life plan – the one where you find a job that you love rather than deferring to retirement. Work-wise, everything else tends to fall into place.

  3. Something like this: If you want things to happen, you can either hope really hard that they do or you can make them happen. Just be aware which of those two paths you’re choosing.

    And no, I suck at taking advice. :-)

    Love reading about and living vicariously through your adventures!

  4. One of my favorite quotes is that “There is no history of something until it happens”. Sort of along the same lines of “if you can dream it you can do it”, I feel that too many people get bogged down by the fact that something seems hard or that no one has done something before.

    I’m not sure what the right answer would be for me on what I want to do with my life. Honestly, I think that I’m nearly getting to the point where I am DOING what I want to do with my life. I have fun at work, but it doesn’t define me. I make enough money to do most of the things I want to do and get to spend time doing the things I REALLY like doing.

    So, if I were to answer the question, I’d say “I want to spend my workday working on something that is truly appreciated and still have enough time and resources to spend with family and do the things that I am pationate about at night.

  5. Great post. Lots to think about. I know a lot of people who struggle with a good work-life balance. (I think DC/NYC are probably hotbeds for workaholics)
    As I contemplate my next career move, I’m definitely trying to take advantage of every opportunity, but also seek out really great opportunities that might not just come my way.

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