* Jedd Thoughts, * Life Updates, Intentional Living

2015 Annual Review

For the last couple of years, at the end of the year, we’ve been doing a practice called the Annual Review inspired by our friend Chris Guillebeau of the Art of Non-Conformity. In it’s simplest form, it’s an exercise to take some intentional time out of your life to reflect on your previous year and to look ahead to the coming year. Here are the main questions from Chris’ original post about annual reviews:

What went well this year?

What did not go well this year?

At the end of 2014 we had just started our unconventional lives and our freelance web service business. Honestly, we weren’t really sure what we were doing and just thought there was no harm in trying. If it didn’t work out, we’d look for regular jobs and say, “at least we tried.” During our 2014 annual review we realized that things went better than we expected. We had no idea what to expect, but what we realized that by the end of that year is that we were happy. We had started a business that was small but providing some income and enjoyed having the freedom and flexibility to travel, to experience new things and spend time with family and friends. Life was exciting and fulfilling. We wanted more of that.

So for 2015 we set one main goal for ourselves: become digital nomads full-time and live the lives we want (with the continued focus being on travel and spending time with family and friends). No more trial period. This is the life want. How can we make it happen? How can we sustain it?

2014 taught us that the possibility existed but 2015 was going to be the year that we hustled. We found more jobs and clients to sustain this lifestyle financially. We let the world know that we did pet/house sitting. We shifted the focus of our businesses to provide services that better reflected our passions and interests (away from just doing things we knew we could do).  We made more plans to visit friends and family around the world and effectively used travel hacking to afford the flights. We were open to new possibilities and projects. We made it happen.

Here are the highlights of 2015:

  • It all started when we rang in 2015 in Hawaii with my family.
  • We followed that up by helping my parents prepare for their move to Japan
  • We visited our good friends in Vietnam and then headed to Japan to visit my parents in their new home (our first visit to Asia).
  • Awesome “tiny house” opportunity.
  • Back to Hawaii for a mini family reunion to celebrate my cousins’ graduation.
  • Celebrated the life of Michelle’s wonderful grandma who was 100 years old.
  • Assisted with coordinating the World Domination Summit 2015
  • Helped to successfully raise $200,000 to launch a new college in Portland called the Wayfinding Academy
  • Traveled to France for Michelle’s cousin’s wedding, did an epic bike trip from Bruge to Amsterdam, visited and made new friends in Denmark.
  • Pet sitting for the month of September.
  • Assisted with coordinating a entrepreneurial conference called Pioneer Nation.
  • Traveled to California for a month long road-trip to visit family and friends, and capped off by Michelle’s brother’s wedding in San Diego.
  • Continued to work with the Wayfinding Academy and a dry, beautiful Thanksgiving with family.
  • A quick, fun trip on a train from San Diego to Portland on points, and a fun working trip in Hawaii to escape the rain in Oregon for a couple of weeks. Bonus – we got to see and spend time with my family.

Reflections of 2015:

  • This life is not possible without support. Recently, my cousin called these people “enablers” and it’s true – we would not be able to live this life without the help of enablers in our lives. People that have opened their homes to us when we had none. People who offered us trade for room and board. Jobs. Etc…
  • What do you value most? This lifestyle makes sense to us but it’s not a great fit for everyone. We’ve designed it for ourselves based on our values (travel and relationships). What are the things most important to you? Do you feel you’ve made intentional life choices that support your values?
  • A whole lot of planning and intentionality is involved. We live by a pretty strict budget (we try to limit our expenses and increase our income). We live simply, most of the time out of a suitcase/bag (we are constantly purging our stuff). We value time over money (almost always, the freedom of making our own schedule is more important than how much money we can make).


What’s Next for 2016: The Year of Launching

In 2015 we spent about 70% of our year traveling. This year because of our commitment to help launch the Wayfinding Academy, we are going to switch that and spend only 30% of the year abroad. The reason for this change is that 2016 will be the year of launches. Michelle and I are part of several different projects that we are helping to launch this year.

Here are some of the goals for 2016 (more details about these goals in future posts):

  • Increase income from the previous year and have money to put towards retirement (both)
  • Travel to another continent and country we’ve never been to before (both)
  • Launch Blogging Abroad website project. (Michelle)
  • Learn another language to the point of being conversational (Jedd)
  • Launch the Wayfinding Academy (both)
  • Do a 30-day “Elimination Diet”. Find out if we are allergic to anything. Fast from bad food. (both)
  • Achieve new fitness goals like being able to do 10 pull-ups or hand stand push-ups. Still determining what this will actually be. (Jedd)
  • Work on being more productive, actually schedule things (Jedd)
  • Help launch new initiatives for the World Domination Summit.
  • Continue to work on our marriage. Have a better balance regarding the time we spend together and apart. Get better at communication (both)

Here’s to 2016.

How To Do an Annual Review?

  1. Get a feel for how to do an Annual Review by reading others: Here’s ours from 2014 and 2013. Chris highlights some of his reader’s blogs here.
  2. Block out some time, at least a day to do this exercise. Find a place that you work best in that inspires reflection.
  3. Find someone to do this with. A spouse, a good friend, a family member. This is a great exercise to do on your own but also to share with someone else.
  4. Use the resources found on Chris’ site and here at Live Your Legend.

Let us know if you have any questions and we hope this becomes a helpful tool for your life.


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