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9 Months of Travel, 3 Lessons Learned, and Why I Quit Software Engineering to Run Team Retreats

I feel more excited about life than I ever have before. Every day I wake up feeling powerful, focused, and ready to leave my mark.

I owe this mindset to the time I invested in self-reflection over a nine month break from work. One year ago today, I walked out the door from my role as a technical product manager at one of the best companies in Seattle. After completing an electrical engineering degree and then working for four years after graduation, I decided I needed a break. I went mountain climbing around the world to test my brain in other ways.

Driving towards the Fitz Roy Massif and El Chalten in Argentine Patagonia during the last few months of travel

I am back in Seattle now, which hosts one of the best job markets in the world for technology careers. I don’t plan on returning to quantitative work quite yet, however. First, I want to apply the three lessons I’ve learned while taking time off. That’s why I am dedicating myself to facilitating team-building retreats for technology companies in the greater Seattle area. Here are those lessons, and why I’ll be running retreats.

Lesson 1: Disconnecting from time to time is necessary to manage the direction you are headed

When I was working a daily job, trying to keep up with my responsibilities, the ever-evolving faces and goals of the organization, the code-named projects, and email, it felt like life was moving at the speed of light. I often left work too tired to remember what I was working towards.

I think this happens to many of us. We don’t have the time or space to really question why. We don’t have the energy to say no, or to organize our output into the things we believe to be most important. We get sucked into just getting stuff done, but what are we really doing? Where are we going? Stephen Covey approaches this busyness in his book, Seven Habits of Highly Effective People. In his terminology, we learn to manage our lives, but we are not often leading them.

I want to lead my life. I quit my job so I could spend time figuring out where I want to end up. I needed that internal conversation to be free of the disruptions and influences that interrupt our day-to-day.

I planned on and went climbing around the world for nine months — this was my time to disconnect. There was a schedule and cadence to it, but I also had a lot of down-time. The still moments allowed me to explore questions like: What do I value? What am I passionate about? What will I look back on ten years from now and be proud of?

I am closer now to my answers to these questions. I spent a lot of time pondering them. I know where I want to head next. Disconnecting from the everyday grind allowed me to figure this out. My answers may not be perfect, but they are a start.

Above: Climbing in Chamonix, thousands of miles from home. This was how I took time to disconnect. It certainly doesn’t have to be this extreme, but this is what made sense for me. The important part is leaving the office and the distractions behind to give the mind time to be free.

After returning to a steadier life and Seattle, I see the process of self-reflection on our direction to be the most powerful tool we have for managing what we all like to refer to a ‘rat-race’. I don’t think “disconnecting” requires quitting your job, just putting down the phone, allowing your mind to relax, and asking yourself tough questions with enough time and space to consider them.

Lesson 2: Healthy, empowering relationships start with quality-time and shared experiences

I spent a lot of the last year traveling with a close friend, Jimmy. He and I enjoyed so much time together, in so many hair-brained situations, that I would venture to say we are closer than quite a few married couples. In my relationship with Jimmy, I feel empowered and supported. He understands what is important to me, how I see the world, my strengths, and certainly my weaknesses. I can say the same for him. I am personally invested in Jimmy’s success because I care deeply about him as a person. I see him as another human who has emotional and physical needs.

This year Jimmy and I joined together to tackle some of the largest and most challenging rock and ice climbs that we had ever attempted. Some of our personal goals overlapped, but there were some dissimilar ones as well. Working through the complexities of choosing how we would spent our collective efforts and limited resources was an important step in growth for our relationship, as was recognizing each others’ strengths so that we could best take advantage of them.

What allowed us to reach this point where we both cared unconditionally about each other’s success and also felt empowered by one another’s support? How did we land at a place where we were willing to drop individual accomplishments for our mutual goals? My belief is that these aspects of a powerful partnership precipitated from spending time a lot time together where we began to understand one another’s needs and values. Our adventures allowed us to move beyond the transactional interactions that define so many relationships in our lives as we live, breath, and work.

And this is the second lesson: if you want to build a strong working relationship with someone, where you don’t feel threatened, and where you are comfortable enough to focus on bringing your strengths to the relationship, start with creating shared, personal experiences.

Above: My climbing partner Jimmy and I standing on top of our first summit in Patagonia. We made this far and found successes through the combination of our strengths.

Lesson 3: We are most creative when we feel safe and relaxed

I started this article with a bold statement: I feel more personal power and drive to pursue what I am passionate about than ever before. I would add to that statement that I feel more creative than ever as well.

While traveling, I spent most of my time outside of the city and away from the computer, and I could feel my mind relax. I had the chance to skirt some of the daily pressures of life and work (Lesson 1), and to build amazing, supportive relationships (Lesson 2). The right side of my brain turned on and I began to consider paths and dreams that couldn’t necessarily be logically supported.

I am beginning to see that working as a software engineer in a corporate environment stifled my creativity a bit. My hypothesis is that the nature of corporate processes, deadlines and quantitative measures of “progress” sometimes suppress intuitive, ‘system 1’ thinking. I also believe we often fail to build relationships with our colleagues that inspire the kind of safe environment we need to voice anything but the most fully-supportable opinions. It does not have to be this way, but we need to manage the environment and ourselves to prevent these effects from occurring. Not only this, but we need to step away from time to time to cool off and relax. When we do feel relaxed in the environment we are working in, and when we feel safe (physically and emotionally) with the people we are working with, we can become the creative, empowered beings we are meant to be.

Team Retreats

What does this all have to do with team retreats?!

Well, with just a small extension to these lessons, I think they apply to teams too. Having worked in high-growth environments, at companies that are focused on continually meeting investor expectations or building the next best thing, I know what it is like to balance multiple priorities all the time. In these situations, it’s critical that we step away occasionally to review where we stand. When we don’t follow through on this need, we get burned out or we iterate down the wrong track, spending precious psychic energy on throw-away efforts. Similarly, when we don’t feel connected and comfortable with our colleagues, don’t feel heard or supported, not only do the best ideas go unheard, but we lose out on the synergistic powers of great relationships.

I see multi-day team off-sites as the perfect way to increase the productivity and creative power of working teams. They provide the chance for teams to disconnect from constant stresses of the office and provide the time and space to collectively consider the direction in which the team is headed. Retreats help to build better working relationships by creating new shared experiences among their participants. From here, a team can transcend to new levels of creativity and engagement that accelerate performance.

Above: The Rolling Huts in Mazama, Washington where we will be running retreats for engineering teams this September and October (no snow involved!)

The retreats I will be running will not include trust-falls, but will build trust. They are about creating opportunities for introspection, strategy discussions, or research, and organic fun at the same time. I am dedicated to creating retreat experiences where an investment of time with your team will return dividends in focus, a sense of shared purpose, and excitement about the future.

To learn more about the awesome team experiences I am talking about, visit northcascadesteamretreats.com

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