The Agenda, Part V: Build a Legacy

The Agenda, Part V

I hope you’ve enjoyed the Agenda series so far. Here’s Part I, Part II, Part III, and Part IV.

Part V, live from my second home at Portland International Airport, brings it all together.


Ultimately, what we want to do is live a remarkable life in a conventional world.

As part of this process, we have the ability to step away from the bridge and ask questions instead of blindly following the crowd. We have the opportunity to pursue a big dream and embrace life as an adventure, instead of something to be lived to its most efficient state. We have the imperative to consider our place in the world and how our lives are interconnected with others.

And ultimately, this creates a question of legacy: what are we building? What will our ultimate impact be? How will things be different after we are no longer around?

That’s what legacy is all about. It has nothing to do with money, inheritance, or even what kind of career we choose. Legacy is also not something to think about at the end of our lives when we can’t make a lot of changes; instead, it’s something to think about from wherever we are in life.

I have an interesting job in that I write about non-conformity and unconventional life, work, and travel—admittedly broad topics. As the movement around non-conformity has grown, I sometimes hear questions like, “If everyone is a non-conformist, who’s really conforming?”

Ah yes, it’s always nice to belittle something in an attempt to render it irrelevant. But the thing is, non-conformity en masse is like world peace—a lovely idea that isn’t likely to happen anytime soon. If more and more people start questioning assumptions, pursuing big dreams, and considering how they can change the world, that sounds great to me. I suspect that those of us who truly feel that way and live our lives intentionally will always be in the minority. But it’s an active, growing minority.

Uncertainty and Choices

As related here, two-and-a-half years ago I was turning 30 and found myself faced with a choice about what I would do next. I had done a lot of things in the previous decade, from being self-employed the whole ten years and volunteering in Africa for four of them, but my work lacked a convergence point. I wanted to establish a writing platform and eventually write a book, and I wanted to create some kind of legacy project that would go on to live a life of its own.

I was also highly uncertain about beginning the journey. I looked up to other author / bloggers, especially J.D., Gretchen, Leo, and Jonathan. I thought, These people have done so much already! What could I possibly add to the conversation?

Somehow I managed to overcome my uncertainty and forge ahead. Whether your legacy project has a similar format to mine or is something entirely different, I hope you can also overcome the uncertainty and choose the road not taken. Or better yet, make your own road.


Building a legacy requires hard choices. Here are my suggestions: when faced with a choice between hope and fear, choose hope. When faced with a choice between abundance and scarcity, choose abundance. (Remember: scarcity is all about seeing the world as zero-sum or winner-take-all. Abundance is about making a bigger pie.)

Ultimately, if you really want to live a remarkable life in a conventional world, you’ll want to do something worth remembering. Live your life out loud. Follow a big dream and find a way to contribute something at the same time. If more people lived their lives in pursuit of a legacy, I think the world would be a better place.

This has been Part V of the agenda series. Today I’m flying to Baltimore—this week continues to Washington, D.C. on Wednesday night and then beyond. See you next from somewhere!


Image: Rowan

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  • rob white says:

    Great question, Chris. I believe the greatest legacy anyone can give is the conversation they leave behind. My ultimate aspiration is to leave behind a conversation that may help others experience their own unlimited nature. These teachings are timeless and have been handed to me from masters from Emerson to Epictetus. Helping others on their own path to self discovery ensures an enduring conversation that can be passed on long after the physical body is gone.

  • Brett says:

    The Agenda has been one awesome, awesome, awesome series. Thanks for writing it!

    With regard to my legacy, the one question I always ask myself is this: have I made the world a better place for my having lived in it?

    If the answer’s no, some soul-searching is needed. However, sometimes we can affect the world for the better by just being ourselves – no grand mission needed. Those are the little victories that we can celebrate even when everything else is going wrong.

  • Jennifer Miller says:

    Legacy… long term vision… so important in a short term oriented, instant gratification driven world! We think of legacy in terms of multi-generational vision… where do we see our family in twenty years, fifty years, a hundred and fifty years? Not just OUR vision, but the vision of the generations before us too.

    Example: My Dad planted trees with me when I was five on his property, intentionally leaving a perfect space for us to build our house in thirty five years later. He mows trails and builds boats with grandchildren in mind. My parents began the legacy of epic adventure travel with my brother and I that we both continue with our children.

    We are not the instigators of a legacy, we are part of the bigger picture, carriers of the torch. We add to the mosaic. So will our kids.

    Visionary business, legacy projects, multi-generational heritage. It’s the big picture that gives meaning to the here and now.

    Love it, Chris! Keep up the encouraging work!! Dream big dreams!

  • Andrew K Anderson says:

    Thinking about legacy has led me to make great decisions at critical points in my life – it’s a trump card in the deck of options! Thank you for writing this series.

  • Sam says:

    Thanks Chris. A much-needed boost for those of us who are, well, still sitting in our cubicles. 🙂 Have fun in DC – one of my favorite cities in the U.S. If you have any free time at all, I’d highly recommend stopping by the National Gallery of Arts if you haven’t visited yet.

  • Linda Gabriel says:

    Love this Agenda series Chris. Thanks so much for this segment, in particular the part where you admit that you were intimidated as well as inspired by others who had already established their voices. I for one am very grateful that you decided to forge ahead. You have added SO much to the conversation!

  • Ellen says:

    “When you have a choice between hope and fear, choose hope” — I believe this is the most crucial aspect of it all. I remember from rock climbing that I was stuck on the wall frozen to death because I was so scared. The longer I waited the weaker I got and no upward movement was possible anymore. After a while I came down, thought of it with the hope to see the sun at the top and climbed again. I did not even notice how quickly I got to the top.

    To form a legacy could also planting a tree. Thank you for your great insights and have a good flight.

  • Daisy says:

    “When faced with a choice between hope and fear, choose hope.” I’m facing some difficult times in my career right now, and I need to keep this in mind.

    No pressure, now — but thanks for the inspiration! 🙂

  • Shazia says:

    “We have the opportunity to pursue a big dream and embrace life as an adventure, instead of something to be lived to its most efficient state.” Words to ponder. Thanks for this series, Chris.

  • Melissa Dinwiddie says:

    Great suggestions, Chris. Thanks for a wonderful, thought-provoking series. You’re certainly leaving a legacy, and inspiring the rest of us who want to do the same.

  • Marci says:

    Just had to say thanks for the small push! I have been re-evaluating my 8:30-5:30, getting home just about dark – not spending enough time with my kids job…and an aquaintance asked if I would be interested in helping with a program “Rachel’s Challenge” at the high school. I recognized the chance to be part of something that would benefit kids and change thier lives. It is something that I would have wanted to do before, but didn’t have enough time. I said not only yes…but heck yes. It is time for me to make more of a contribution. Thanks for the small push:) Love your site.

  • Marla Miller says:

    Since discovering your work/site, I feel like your messages are speaking to me. I’ve been working on a project that sidles up to ‘aging’ but doesn’t speak to it directly. In recent weeks i’ve realized the project is bigger and in no small way, your words/perspective have influenced this.

  • Krys C says:

    Really enjoyed the Agenda series but I have to disagree with you on your statements in ending:

    I personally don’t believe you need to do something MASSIVE to live a remarkable life in a conventional world. Some grandiose dream, some huge thing no one else is doing to ripple down through the ages. . .I think being a good parent or a good friend, can be remarkable. Quietly standing your ground, sticking to your morals. . .these things are remarkable, if not global.
    Personally, I’ve got starry eyes and big dreams. I have a few friends that confessed they felt I ‘looked down on them’ because they weren’t traveling globally, or dreaming of changing the world. But I didn’t, at all. I think being true to yourself can also include accepting that the massive life project, or world travel thing is NOT for you. While a lot of people fall into the pattern of ‘get married, buy a home, start a family’ because that’s what society dictates, others do it because that really is what they want.

  • Mark Dowling says:

    Hi Chris, “If everyone is a non-conformist, who’s really conforming?” is actually an interesting point & I don’t think it belittles what you & others are doing. Conformity (or non-conformity) are relative terms, & what you are doing is shifting the status quo. That’s really important, massive in fact. Non-conformity today becomes conformity tomorrow. Isn’t that just another definition for progress?

    I’ve been a lurker on your blog now for many months, & your art, as I see it, is to show people the adventure that’s everywhere, right in front of us, if we just take the time to see beyond our (conforming) viewpoint.

  • Evan says:

    I would like to leave a changed world. One with more equity and compassion in it. If I can do this and live an unremarkable life, that is OK by me.

  • Stephenie Zamora says:

    Loved this series. Your past post about creating a legacy project had a profound impact on me during a time of serious soul searching and self discovery. I had never heard the term before and really wrapped my brain around it. Since then, I have expanded it into something amazing that I can’t wait to bring to life. I’m working on a piece of it right now and enjoying every moment. I’m glad that you were able to overcome your uncertainty and “forge ahead” because you are making a huge difference for a lot of people!

  • Molly Gordon says:

    I’m glad you mentioned the people you look up to, Chris. Too often, I find, my clients think their legacy has to be something unusual or distinct from what others are doing. A legacy doesn’t need to be unique to be powerful. It just needs to be something deeply important to you (and bigger than yourself) to which you are willing to devote yourself over time.

  • Natalie Sisson says:

    I decided many years ago to live my life as one big party – as in to celebrate it every day and help others to do the same.

    In my business world I tie that in with helping women entrepreneurs to create freedom in business and adventure in life.

    I’m fulfilling this legacy everyday. My question to Rob White is – do you also want to create the conversation now, not just leave it behind when you’re gone?

    I’m sure you do, and you probably are. Go for it


  • Lilian says:

    Chris, thanks for the series.I was uncertain and stuck in the crossroads until I reread what you’ve written.I am going with hope, by going ahead with my own path.

  • David Trotter says:

    So often it seems like prominent people try to leave a legacy that points to their own greatness…frequently in the form of a building with their name on it. Although most of us may not be able to afford such a ‘legacy,’ it’s tempting to buy into the subtle lie that a legacy is all about what I’ve achieved that I get to leave to others. A generous legacy is one that is left each day that I’m alive…not just when I pass on to the next life. How are my words, attitude, and actions a legacy left in the hearts of my family, friends, and clients?

  • Karen says:

    To me its not so much about being a “non-conformist” as it is about being your own “authentic self”. I see it as a matter of navigating your life from answers from within as apposed to following what we see around us externally. The result of being internally directed may appear to others to be “not conforming” but that appearance is merely a symptom of being true to oneself.

    That aside I have derived much courage and motivation from what you are doing and you have my absolute appreciation and gratitude!!

    ps. I looked for your book in two large book stores in Bangkok, but sadly not there?

  • Jadyn says:

    Leaving a legacy is such a great way to approach life – not just living for what brings pleasure today and not even making a good future for ourselves, but thinking about what we leave behind. I think we all leave a legacy to some extent in the hearts of our loved ones and every time we make a decision that is rooted in love rather than fear or other motivating factors. However, I am also really liking the idea of coming up with a project that will bless people beyond my circle of friends and family…thanks for giving me food for thought on this.

    On a different note, it sort of baffles me that people ask “If everyone is a non-conformist, who’s really conforming?” as I think that the beauty about people is that we are all wired differently and I think that even if everyone decides to follow their dreams, we still wouldn’t end up with a set way of life that would work for all “non-conformists” therefore rendering it “conformist”, because every person would forge their own unique path.

  • Bekah says:

    Your statement “These people have done so much already! What could I possibly add to the conversation?” really hit home with me. Last year I was faced with the same question when I started my blog. It took awhile to get through the question and just forge ahead. I am so glad I did. Through my work I have met a new community of amazing people and have immersed myself into a sport that I love. If I would have answered the question with “nothing” I never would have what I have today. It still is a hurdle that I have to jump over every time I do a post or reach out to people, but each time that hurdle gets smaller and smaller.

  • Wyletter Whaley says:

    I am enjoying ‘The Agenda’ series. I particularly like this part on legacy. We live in a short sighted, today driven society that often gives little thought to tomorrow or the impact on community. I believe that our world would be better if we all asked ourselves what our legacy will be. We all leave a legacy. The question is what type of legacy do we leave.

  • M Ryan Taylor says:

    I really have enjoyed this series of posts.

    Sometime late last winter, I set what I thought was a crazy goal, to do all 60 of the hikes in this book we found (60 hikes within 60 miles : Salt Lake City). That might not sound crazy, but I had reached an all-time high weight of 424lbs and lugging and extra 250lbs of weight into the Wasatch mountains was a big deal to me. My wife and I completed 37 of them this Summer and I’ve lost about 60lbs (long way to go still).

    Mid-Summer I found your blog, and have been following with increased interest, got the book, and as I said, love this series of posts on ‘the agenda.’ It’s been an extra measure of inspiration in my quest for health.

    As a musician, I’m not quite sure what kind of legacy I will leave behind, but I’m going to give it more thought. For now, the health quest is the biggest thing for me. That way I’ll be around long enough to figure it out at least.

  • Coach Dawn says:

    Great post and I hope (and believe) that I am in the midst of leaving a useful legacy that I can be proud of…it’s exciting when you think about it!

  • Karen Divine says:

    Legacy can be as simple as making a connection with the person at the counter or allowing someone to help you with something. It’s as simple as being compassionate and forgiving during challenging times. I am 58 and have always chosen the non-conformist life. When I was young I read Krishnamurti’s book on Fear and learned that the only way through our fears is to confront them, so I mustered up Courage and took the walk and each time I did I realized there was nothing there to be afraid of. One must go through the fire in order to get to the other side. It’s the only way out. I also did Tony Robbin’s 30 ft Firewalk and NLP training in the 80’s and learned how important it is to become CLEAR about what we want in our lives. We cannot move forward towards something until we know what it is. Sounds basic and it is, however sitting with oneself and being honest about what we want in this life is the first real step.

  • Knapyhed says:

    This series has been terrific! You’ve given the AONC nation much food for thought. This series along with your book are 2 items that are on my list to be reviewed on a regular basis to help me stay focused.
    Thank you Chris Guillebeau where ever you are.

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