Annual Review: 2009 Life Lessons


This is part of my end-of-year series while I’m away on vacation. Future posts will cover business lessons learned, a travel roundup, a list of every post from 2009, and the shape of things to come. Happy December!


2009 has been a truly amazing year for me personally and for AONC. It’s no exaggeration to say that my entire life has shifted dramatically from the place where it was a year ago.

Of course, the past is history. Once in a while it’s good to look back, which is what I do during this time… but then you need to move on to avoid getting stuck in Glory Days. We’ll be moving on shortly, but first, here are a few things I’m proud of from this year:

  • Published 279 Days to Overnight Succes manifesto
  • Never missed a scheduled post (120 so far in 2009)
  • Sold the book proposal and wrote the book
  • Began the shift to a real, sustainable business (four product launches, new Unconventional Guides site, merchant account, etc.)
  • Established a new home base in Portland, Oregon
  • Starting writing for other outlets (newspaper column, CNN, Business Week, etc.)
  • Traveled to 20+ countries (I’ll list them all in the upcoming travel roundup)
  • Ran two half-marathons
  • Hosted AONC Meetups in 7 Cities


Here are a few themes that emerge as I look back on 2009.

Writing a book is hard but good. I’ve been an active reader for most of my life, and I’ve noticed that some authors like to whine about how hard it is to write a book. You know you’re encountering a whiny author when you run across an acknowledgments section that reads something like:

“Writing this book was the hardest thing I’ve ever done… thanks to my family for leaving me alone for [long period of time] so I could undergo this heroic task. I’m glad it’s finally done.”

I understand that the effort may be herculean if you’re writing War and Peace in longhand, but otherwise, writing a book is like any other kind of hard work that needs to be completed over time. As such, I didn’t whine (OK, not too much) about the writing process. It was hard but good. Next year I’ll be working on the proposal for the second one, so if you’re out there and have also been thinking about writing your own book, I won’t be the one to dissuade you. Go for it!

To sustain a long-term commitment to creative work, you have to be excited about the work itself. It has to become sacred to you. This year I grew to see my main occupational identity as a writer, and I learned to structure my workday around everything that process involves. These days there are all kinds of distractions to keep me from writing. Sometimes I successfully resist them and sometimes I give in; the important thing is getting up the next day and going back to it.

Also, the more you do something, the better it gets. When I read through the early AONC archives, some things I like and some things I don’t. I keep everything there as a monument to the reality that the creative process rewards discipline. I believe in the 10,000 hours theory – keep working, keep improving, don’t be afraid to take risks, and so on.

Empowerment of others is always the best choice. Generally speaking, if you wake up one day and aren’t sure what to do with your time, do something small that helps someone else. As a nice side benefit, you’ll probably feel better as well. It’s hard to explain this in a short summary paragraph, but I’ve tried – and will keep trying – to decentralize any celebrity aspect of my work. I want to correct false impressions about unconventional living (Fearless? Not me), help others to see the possibility for growth in their own lives, share everything I know about self-employment, travel hacking, challenging authority, and so on.

Stay tuned for more and more of this focus in 2010, and thanks for sticking with me thus far.

“Ubiquity is the new exclusivity.” This advice came from Gretchen Rubin, originally in the context of writing for Huffington Post and other outlets. I immediately identified with the idea and latched on to implementing it. I do 15-20 blog or journalist interviews a month. I’ll syndicate my work for free with any reputable outlet. I follow the Google Alerts for my name and leave comments responding to the posts whenever possible. I post on Twitter 10-15 times a day. For the right kind of major media profile, I’ll fly across the country at my own expense.

Gretchen’s insightful comment, and my perspective as well, reflects the idea that it used to be a big deal to become a highly-specialized expert, but now it’s a bigger deal to be everywhere all at once. It works well for me, and I have no plans of slowing down. (I wrote about a few related concepts over here.)

Say yes more often. Speaking of ubiquity, I say yes to all kinds of things. Why not? I used to think of this as a personal weakness – because that’s often what we’re expected to think. But in general, the more I do, the happier I am.

Granted, I say no a lot too – in fact, sometimes my default response to engagements is no because there are so many opportunities. The difference is that I try to say no to anything I wouldn’t enjoy, be a good challenge for me, or otherwise help someone else. I try to say yes to opportunities for personal growth, collaboration with like-minded people, and anything especially interesting. When Air New Zealand asked me to go to the Cook Islands on less than a week’s notice, for example, I had plenty of other things I was working on at the time. But I said yes, moved the other things around, and had a lot of fun.

“Wealth is in our friendships.” Jen Lemen gave me this advice when I asked about how to manage relationships as a sphere of influence grows. I know it doesn’t always come across this way online, but I’m a fairly introverted person. This year my circle of friends has expanded from a small, mostly local group to a broad range of 1,000+ people all over the world.

This is in addition to everyone else I talk with on an occasional basis. I think I have personally interacted with more than half the AONC readership (currently about 20,000 as a core group, and a larger number of people who drop in once in a while) at some point or another.

Some people say this practice is not scaleable and that eventually I’ll become an asshole like anyone else who becomes Internet famous. It’s hard to know for sure, but my model for scalability and awesomeness continues to be Seth Godin. Seth writes the number one business blog in the world, and yet if I write to him about something, he’ll write me back the same day. Whenever I log in and download 200 new messages after a day of traveling somewhere, I always think, “What would Seth do?” and then it’s no problem to answer them all, even if it takes a while or I get behind.

Also, I don’t make a distinction between online and offline friends, and I don’t view relationships with readers as passive or impersonal. In 2009 I met several hundred readers in real life, and almost without exception, we pick up right where we left off in the online world. As Liz Strauss says, “You’re only a stranger once.”

So thank you, friends, for caring enough to read AONC. (And I’ll have more to say about this shortly, in another year-end post.)

Your Turn

Since wealth is in our friendships, I always enjoy learning from everyone who reads or participates on the blog. Now it’s your turn: what have you learned in 2009? Feel free to share a couple of your own lessons with the rest of our group.

As with Monday’s post, however, don’t just keep it here – consider sharing your 2009 lessons with your own circle of influence. We could all learn from what you have to offer.


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  • Jay Schryer says:

    “Empowerment of others is always the best choice.”

    Yes, yes, a thousand times yes! This is one of the mst important lessons to learn in life. In fact, I believe (as many others do) that this is what life is all about. And at this time of year, I believe it should be in the forefront of everybody’s minds. How much better would the world be if we all lived according to this principle!

  • Ted Hessing says:

    Chris, let’s limit this response to things I learned in 2009 from you. That list is long enough!

    1 – Tell an honest compelling story. I am consistently amazed at your openess and willingness to share. It’s no wonder your small army is such a vibrant community and source of strength. My obsessive privacy complex may be counter to my other goals.

    2 – There is still room for excellence. In a world where ‘the tall poppies must be cut down’ your efforts show that the superlative, interesting and unconventional are not only acceptable, but rewared. The other commentors and guests that you feature also demonstrate this phenomenally well. There is no need to be second rate – leave that to them that will copy you. Be your own standard par excellence. Others will follow.

    3- The phrase ‘plan your work; work your plan’ is alive and well here at AONC. While there is of course room for ‘walkabout’ (lots and lots of room), if you want something, make a plan, work that plan, and go!

  • Nate says:

    Chris – Well, I’ll just say a personal thank you here. It was reading your blog that got me started on my own journey of change, although I’m still in the very, very early stages. I think the biggest catalyst was reading your Break out of the 9-5 ebook. It really showed me that there are unique and unconventional things you can do to make a little money. It doesn’t have to be a traditional job per se.

    It’s wonderful to see your success and although I’ve never met you, you come across as an incredibly genuine person who really cares. I think that’s what’s important in the blogging world.

    Thanks and I look forward to following your journey in the coming years.

  • The Frugal Hostess says:

    I’ve been thinking a lot about the experience of meeting internet friends IRL, and I think you just gave me a breakthrough. I’m always surprised that my online friends aren’t more extroverted (like me), and I always feel like I overwhelm them to death. I would’ve definitely thought you were an extrovert, so (as dumb as this sounds) it’s good to realize that I shouldn’t expect the person’s real life personality to match my perception. Duh, I’m sure a four-year-old could have drawn that conclusion, but I’m a self-centered extrovert! Also, I’ve been amazed to get email or Twitter messages from you, so I can testify that you are doing what you say you’re doing and haven’t turned into an internet famous douche yet. Congrats!

  • paurullan says:

    Thanks to you for the hard work! Keep going!

  • Josh Wilson says:

    Hey Chris,

    Great to read your end-of-year-lessons-learned report. You’ve definitely pushed me to start doing things that I’ve only talked about. I continue to reference your manifestos to keep me moving. I’m hugely impressed by your consistency with posts and replies and everything else. But where do you draw the line on ubiquity? Do you draw a line?

    Here’s maybe a better way to put it – let’s say that you aren’t a full time writer/online hero, and are doing other stuff and trying to communicate and build followers at the same time? Is ubiquity the only way? How can you use social media (the phrase even rubs me the wrong way) without social media owning your every waking moment?

    Anyway, nuff of that. Here’s to 2010!

  • Kevin says:

    The most powerful lesson I’ve learned this year is that for me to be happy and live a motivated, meaningful life, I must always be thinking about some new idea or exciting possibility. If I only live in the “now” without dreaming ahead, I have no impetus to excel, no future hopes stoking the fire of the present.

  • Juliet says:

    The main thing I’ve learned in 2009 is that (for me) time largely isn’t worth trading for money, and especially not in the standard 9-to-5 five-days-a-week mould. Turns out I’m happier with less cash and more time spent doing things I enjoy and value but which don’t pay.

    I also found out that it’s entirely possible to support myself at a level that I’m happy with without full-time paid work, and with the paid work I do choose to take on being work that I love.

    I also got back from 10 months of travelling (which had a big part in the above lessons) and concluded that I have *way* too much stuff in my house. I’m working on fixing that!

  • ABCcreativity says:

    “To sustain a long-term commitment to creative work, you have to be excited about the work itself.” i love this, and in 2009 i found more ways to get more excited about, and committed to, my creative work.

  • Kylie says:

    My greatest lesson this year has been that we truly create our lives through our actions. I knew before that life does not simply “happen” to us and that we have the power to create the life we want, but I never put this into practice as much as I have this year. I’m now preparing to do your annual review process in order to fulfill my vision of what next year will be, thanks to you and the inspiration I got from your manifestos.

  • brian says:

    After traveling extensively the early part of the year I reached the same conclusions you did. I miss the road, but I appreciate being amongst family and friends because I was on the road. Missing home and missing the road have a proportional relationship.

  • Wayne says:

    Preparation over Perspiration……Motion over Mediation…..Action over Reaction….

  • Patrenia says:

    Lessons learned in 2009? To just get out in the world and really “just do it”. I know we’ve all used that quote many, many times, but this year seemed like the right time for me to break free. Thanks for helping to be that inspiration:-).

  • Kangai says:

    Hey Chris.

    Thanks for this, and every other post you’ve.. well, posted.

    I guess the one thing I’ve learned this year, especially from you, is the art of discipline. You mentioned that you’ve not missed a post once, and I think that’s a testament to how disciplined and committed you are.

    I guess once you find something you absolutely love doing, being disciplined is that much simpler (not easier, though).

    Thanks for keeping your promise to us- your loyal fans. I personally appreciate what you write, and how much fun you have while you do what you love.
    It’s given me sike (Swahili slang for excitement) to go out and do my own thing fearlessly and courageously.


    ~Kangai, from Kenya~

    I just graduated with my degree in international business. It’s even cooler because it’s taken me almost 9 years! (it’s a long story…)

  • Jon says:

    Well Done Chris. Congrats on each achievement! Glad to see you living and enjoying life to the full.

  • Kendra says:

    Hey Chris!
    I loved your end of the year review & your process for planning your next year. I can’t wait to sit down & hammer mine out (after finals week of course).

    Just wanted to say you are one of my favorite bloggers and I love the ability you have to span many topics and still make them applicable to nearly everyone.

    This is one of my favorite posts so far! I know you just relocated recently to Portland, I’m considering moving to the outskirts of Seattle, so we’ll be almost neighbors!

    All the best,

  • Rachel says:

    Fantastic post, Chris, and really inspiring/insightful life lessons. Ones that particularly resonated with me were:

    – Writing a book is hard but good. I have so many friends who have written books and who complain about it via social media. I’m writing a book and complain about via social media myself. I don’t think this complaining is all bad – it can serve as a kind of community reassurance that other people find the task difficult also – but it’s also helpful to not think of it as a Herculean task unlike any other.

    – “Ubiquity is the new exclusivity.”

    – Say yes more often. Like you, I’m happiest when I have a lot on my plate – I feel more stimulated, excited, energised… I do wonder though how to best balance that impulse to say ‘yes’ to things that sound like they will be fun (and almost invariably are) with the kind of focus that we’re told is necessary to reach the really big goals. How do you best manage a multi-goal life?

  • Srinivas Rao says:

    What I think is amazing and important for people to take not of is how far you have come in a year. You’ve been persistent, you had goals, you worked on accomplishing those goals and you’ve accomplished them. That’s awesome. With regards to relationships, I’ve found that the more I end up talking to somebody the better the relationship gets. I often talk to people on skype and even do audio chats because it seems to increase the authenticity of the relationship.

  • Sandy says:

    Thanks for the year end review. As I head into 2010 and my 51st year facing a major shake up it is so encouraging to read your blog. You continue to inspire me to see things from a non-conformists perspective and to stop envying the status quo.

    And so, I am seeing 2010 as a chance to reinvent! People in my stage of life need to see someone doing this and I can be thankful to have the opportunity to be that person.

    Your optimism is contagious. Keep doing what you do.

  • Nathan Hangen says:

    Chris, this is one of my favorite posts of yours in recent memory.

    I remember when I first starting reading here over a year ago, before the new design and the massive amount of recent work you’ve completed. I could see you were on your way, and I’m very excited to see that I was right.

    Keep leading the way and being a trailblazer. And thanks for being an inspiration while I was overseas.

  • Evan says:

    2009 business-wise has mostly been finding out what doesn’t work for me as far as making money goes. Affiliate stuff, selling my own products and so on. Not sure where to next.

    I have learned I really don’t want the 9-5 lifestyle, so long as I can make enough to live frugally I’ll avoid the 9-5 thing (too much useless work, too much petty office politics, too much hassle to get anything worthwhile happening).

    I’ve learned that where you live can have a big impact on quality of life – moving away from cold winters soon.

    I’ve learned that I can persist for the long haul even if not ‘successful’.

  • Judith Nelson says:

    I just found your site. I am giddy with excitement on setting my goals for my life moving forward. I have spent 39 years working for someone else’s agenda – time live my life starting at age 60. Thank you for your insight and honesty.

  • jenx67 says:

    I hope you make it to Oklahoma in 2010. If you do, I’ll help gather together your meetup!

  • Jonathan Campbell says:

    Huge post! Love the No vs Yes. Saying yes to lots, but in particular say yes to ‘opportunities for personal growth, collaboration with like-minded people, and anything especially interesting’

    I learnt that:
    *Going outside is important and has a major impact on my happiness.
    *NOT smiling is unattractive. Smile more and you will be come a mirror for other’s smiles.
    *I should be outstanding every time I am standing up
    *Some soy milks don’t dissolve in instant coffee.

    Currently in competition to book an international flight as close to departure time as possible. Be good to book a seat AS it’s boarding.

  • thebearwallah says:

    This year the local Chocolate Shoppe packed up and moved. No more friendly cafe with triple hot chocolates. Life lesson: expect that your world tomorrow may be a different world.

    Now, if only I could figure out what ‘ubiquity’ meant … Bear

  • CJ says:

    Thanks for the guidance on doing an end of year review, in addition to goals for the next year. I’m in the process of doing my own goals for 2010. Among them are to devote time to a couple of entrepreneurial and self-improvement ventures. ’09 involved several leaps of faith and tackling some fears head on (nothing like doing “open mic” at a comedy club for the first time!). I hope to take that momentum further next year. Thanks for sharing your “like mind”, Chris!

  • Jack Woods says:

    Chris, there are going to be 9 students upset with you on Tuesday, you just gave me a great topic for an end of the year student essay. I think I will join them in writing my life lessons from 2009.

    I don’t think I am ready to write about my lessons from the 2000 to 2009 yet.

    Thanks for the great post and the great idea.

  • bondChristian says:

    1. It’s more important to keep friends than to be right. This of course is a give/take relationship. Up until now, though, I’ve focused on being right too much. While I still believe it’s important to be right, there’s a certain level of grace there that’s crucially important. This goes along with the “Wealth is in our friendships” lesson.

    2. I already (pretty much) have all the info I need. It’s just a matter of working my face off to succeed (via Gary Vaynerchuk mostly).

    3. Therefore (from the first two), encouragement is the most important thing.

  • Scott Webb says:

    I should look up when I discovered the art of nonconformity. I know this site and yourself have had a great influence on myself.

    I plan to do a post like this and link here.

  • gabriela masala says:

    2009 Lessons…in no specific order…
    1. Follow The Dreaming.
    2. Take MASSIVE action in lifestyle design.
    3. Command my Sacred Space.
    4. Put people before things.
    5. Prioritize Play.
    6. Love Radically.
    7. Be a universal citizen in addition to a national and global one.
    8. Relax into life as the ultimate spiritual path.
    Thanks Chris! You are very inspiring!

  • Scott Webb says:

    @Sandy, I recommend reading a book called RENGEN. I am in the process of reinventing myself, and I am partly through the book. It’s right on point and would be inspiring for moving into 2010

  • ian anderson says:

    I came to NZ for a while to take a supporting role at home while my wife worked. On one salary:-

    (1)I learned that half the stuff we used to buy we didn’t need.
    (2)That most of the stuff we wanted we didn’t actually need.
    (3)Most of the stuff that the kids had the most fun with was actually free.
    (4)That just because a place looks good on paper and lots of other people say it’s cool, it doesn’t mean that it is right for you.
    (5) That you need to ‘connect’ with the place that you chose to live.

    And lastly, that the old cliche of ‘to meet extra ordinary people you need to do extraordinary things’, is more true now than ever.

    Merry Christmas Chris and a Happy New Year to you and yours,

    p.s. looking forward to hearing all about your journey next year!

  • Sylvia says:

    Lessons learned – Food – Shelter – Everything else is a bonus. Enjoy life!
    All the best to you Chris! 🙂

  • Peter says:

    This has been a year of change for me as well. I had to give up paid employment but discovered new ways to use my existing skills. I also rediscovered the importance of listening to people and their stories, which I have not had time for in the past few years. I expect more developments in the next few months.

  • Allison says:

    Hi Chris,

    Thank you for sharing your lessons learned of 2009! I have been following your blog for just over a year now, and it’s truly wonderful to watch you grow throughout the year and now read back on your reflections on what you have learned in the past 12 months. They are, as usual for this blog, sincere and thought-provoking.

    The most important lesson I learned this year is that you cannot think your way to where you belong. If you are not happy, then you need to keep moving forward. I realized this when I made a decision to drop everything in Boston, take the biggest risk of my life and sign up for a cross-country bike trip to support the affordable housing cause. The AONC community has been very powerful in that it helps me know that there are lots of other risk-takers out there who follow their dreams, instead of doing what is easiest or the most comfortable. Thank you for everything you do! Happy holidays and happy new year.


  • giulietta nardone says:

    Great lessons you shared. Love that you find the time to respond to your readers. This leads me to my two greatest lessons for 2009:

    a) We all learn from each other
    b) Everyone has something to contribute

    Much thx for your 120 posts this year!

  • madaline says:

    1. RESILIENCE is a GIFT money can’t buy.
    2. Always follow your gut. It can SAVE your life. It did mine.
    3. It takes COURAGE to turn against a tide. Well, that is most often where an AUTHENTIC LIFE begins.
    4. Sometimes you have to THROW OUT everything you believe in to THRIVE.
    5.When facing a life threatening disease: LEARN something that takes patience and a lot of PRATICE. Even on days when you are too sick to do it, you will have something new and challenging to look forward to. It strengthens patience, PERSISTENCE, faith, and encourages compassion!
    6. The people who show up when you are in trouble are not necessarily the ones you thought they would be, that is GRACE.
    7.How you handle an unexpected challenge determines your HAPPINESS, HEALTH, and ability to experience WONDER.
    8.The smallest KINDNESS can HEAL a broken heart that is willing.
    9.It is never too late TO BE HAPPY if you are WILLING TO LET GO of how you define happiness.
    10.In these times: those who are FLEXIBLE FLOURISH.

  • Maria Brophy says:

    Chris, I think your message is the most important of all the blogs I follow. Essentially it is that you can create the life of travel if that’s what you want. Anyone can do it.

    This year: I learned that the world won’t come to an end if I am brutally honest about my mistakes and screw ups on my blog for Artists. In fact, it makes people want to read my articles more, not less.

    I learned that I can commit to a craft and if I work at it every day (like writing) then every day, I get a little bit better. (The power of gradual)

    And finally, I learned that though I love love love money, I’m happy even when the economy is down (and my income cut in half). I’m happy no matter what, as long as I’m creating my own life of doing work that I love, traveling the world, and being with my family.

  • Jennie says:

    Just wanted to say that I look forward to your e-mails and have enjoyed your e-books, very inspiring. Thanks for such great content, keep it up!

    Meanwhile, I am learning how to stay focused on a business plan (and how hard it can be) as well as working up the nerve to travel long-term (as soon as I am generating consistent income from my business)!

    Happy Holidays!


  • Andi says:

    As always, your words are awe-inspiring! May 2010 be your best year yet (though I have no doubt it will be)!!! I learned this year that I seriously can accomplish anything I put my mind to. I’ve always believed in myself, but every goal I made this year I set and then some! I’m so excited to make even more goals for 2010 now.

  • LeoArtetaV says:

    I’ve learned to enjoy and look for the eternal amaze that aparently lies dormant in every bit of this surrounded reality. I’ve found this group, which helps to widely spraed the art of living helping others.

  • Victoria says:

    A great read, as always, Chris. I know you’ll hear this a lot, but thank YOU for sharing!

    I’ve been doing year end reviews and plans for a while now – I do this from birthday to birthday (instead of January to December). I tried out your template last year, and, well, it’s a lot more organized than the lists/sketches/doodles I’ve been using. I met a lot of goals in the past year because of it.

    As far as lessons go, I learned most from one weekend, when a typhoon caused a flood that submerged 95% of the city I live in:
    1. I don’t need as much stuff as I thought I did. 2. Count my blessings, everyday. 3. Opportunity is everywhere, as are heroes.

    I hope you get to keep writing!

  • Mary Golubeva says:

    One of the most important lessons I’ve learned this year was the fact that the world is very big and full of people whom you can help, and who can help you on the way to the life that one really want to live. You’re not alone, and if you want somthing, just do it, and Universe will help you 🙂
    Chris, I admire what you do, and though I read your posts just occasionally, I always find something very valuable and inspiring. Keep going!

  • Jordy Clements says:

    I learned a lot from life this year and a lot from you personally, Chris. This was the year I bought in fully about making a career on the Internet. Seeing you and other successful writers/thinkers made this seem possible. While my personal blog remains a personal endeavor,, an entrepreneurial venture I have a 50% stake in, continues to excite me and scare the crap out of me. I think the most important thing I learned from AONC was the concept of personal branding. Perhaps not as uplifting as the more motivational messages on this site, but certainly the most important one for me. 2010…New Year, new goals, can’t wait…

  • charlie ahern says:

    In 2009 I learned a lot about what makes us really happy. Although the economy has hurt many of us, I learned the importance of optimism and the relative insignificance of materialism to our long-term happiness. My two favorite (not new) books for the year are “The How of Happiness” by Lyubomirsky and “Learned Optimism” by Seligman.

    I gave several speeches on these themes in 2009. In a year of so many struggles, people appreciated learning about how they could improve and enjoy their lives.

    Your comment that “Wealth is in our friendships.” focuses attention on what’s really important in a happy life.

    I’m looking forward to your “Empire Building Toolkit.”

  • Wyman says:

    Thanks for the review series and the rest of the 120 posts. I have read them all with comments. Your readers are top of the line. Only 3% of people write their goals and they all seem to be following your. God bless 2010 and all the entrepreneurs who refuse to accept the recession. It is a great time to change direction. I’m starting out new at 72.

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