The leap.

30d3176299e211e19dc71231380fe523_711,305 days ago, I started my career in advertising. Since then I have worked fulltime at nine agencies. In the spring of 2004, I freelanced briefly and also managed to write The Creative License.  Other than those brief months, I have spent most of my hour as an adult employed by other people and working on whatever they wanted me to work on.

When my boy entered high school, Patti started asking me, “How much longer are you going to do this? When Jack goes to college, will you finally stop? Aren’t there things you’d rather be doing?” For most of my career, my mum has asked me, “How can you stomach working for corporate America? When are you going to  give it up already?” Most of the people I work with have, at one point or another, asked me, “Don’t you make enough money from your books to stop working in advertising? It’s amazing you have done so much while holding down this job. Imagine what you could do if you did it full-time.”

I’ve done a lot of shrugging and changing of the subject over those thirty years.

A few months ago, I realized something had to change. I liked my job but I wasn’t growing any more. And it seemed like I spent a lot of time with my nose pressed to the window of my nice office, looking out at the wide world where so many people seemed to be doing so many interesting things. And now Jenny was echoing Patti, asking me if I wouldn’t be happier focussing on art, films, books, teaching, speaking…

With Jack happily at RISD and with no more real day-to-day obligations except walking my dogs, I realized I no longer had to make excuses to myself. I could finally try out something new.

I am writing in this in my empty office. The surprisingly few possessions I have accumulated over the past nine years here are in a bag and I am watching the clock for the last time. It’s my last day and in half an hour or so, I will step into the next chapter of my life.

My next steps are far from complete and I have realized what a luxury that is.

But I do have a big wish list to tackle. My editor at Chronicle is working with me on a really exciting new book project. I have the outlines for three others just waiting to be tightened up and sent off. I have written all of the first online class I will be teaching. Now, I just need to shot a bunch of cool videos to go along with it and release it to you soon. I have a big stack of art books I want to reread and study. There are so many galleries and museum shows I want to attend. Jack and I have some art projects we want to work on before he goes back to school. I have a long, long list of things I want to write about for my blog. I have several new invitations to give talks and workshops. Several very interesting new projects have just come knocking on my door that could open all sorts of new directions. And there are so many people I’ve met over the years, wonderful inspiring artists, who I want to get to know better and to find ways to collaborate with.

Most importantly, I am also keeping a large chunk of time open for serendipity. Open space that is reserved for adventure. If you have any you’d like to send my way, fire me a note.

The first big adventure: going bi-coastal. In September, we will be renting an apartment in Los Angeles and for at least a year will work there and here in New York. A fresh address, a fresh perspective, and loads of fresh possibilities. I can’t wait.

Well, I better go and say my last round of goodbyes, grab my bag, punch out for the last time, and head off into the sunset. See you on the trail!


  1. Jazz

    How I envy you! Good times ahead I’m sure.

  2. Elizabeth MacDonald

    Congratulations on the Leap of Faith!

  3. leighbunkin

    Bravo! Will look forward to all the wonderful projects you will be creating!
    So excited for you.

  4. Elsie Hickey Wilson

    Best wishes and so pleased to read this! Go, do, live, and keep leaping!

  5. Ann Dermansky

    A grand jete! Congratulations.!

  6. JaneLaFazio

    wow! congrats, Danny! Time for a new chapter, a change and a new adventure! woohoo!

  7. leighbunkin

    Bravo! Looking forward to all the wonderful projects you will create.

  8. bohemianopus

    Good luck to you. I KNOW you will be a huge success!

  9. broworkshop sketching

    My admiration for you is almost infinite.
    Taking this step is really what makes you enough free to say you are devoting your life to art.
    Congrats and good luck from the bottom of my heart.
    Maybe, one day, I hope I will follow your example.


  10. Karen (the Netherlands)

    Wow! That is so cool, I’m happy for you, and wish you much success, but most of all a very happy life. It’s so good to be able to do the things you ‘have’ to. I’m curious for all of your new adventures! Have fun, my artistic friend. Thank you so much for all your inspiring words and drawings. God bless you!!

  11. Elaine

    Talk about serendipity. Just discovered your blog two days ago, and now today, you are leaving your job and all I’ve been thinking about for days is leaving mine. Whoa!

  12. claudomin

    Yes! Well done Danny. You are an incredible artist and you will have wonderful adventures. May the good times begin!
    Claudia D.

  13. donmcnDon McNulty

    Good on ya Danny, all the best! I am looking forward to hearing about your new adventures, taking your on line course, continuing to have my drawing life refreshed and inspired by you, thanks a ton Danny.

  14. artquiltgirl

    I am so extremely happy for you….jealous, as well. It will be a wonderful new beginning for you, you have so many new adventures coming your way! Best Wishes Danny!

  15. Nymph Du Pave

    I am so happy for you!

  16. Suhita Shirodkar

    Good Luck with your new adventure, Danny. You’ve always been an inspiration, and I look forward to lots of new ideas, fresh projects and exciting books!

  17. Christina Breid

    Congratulations on your next chapter…it’s an exciting time in a person’s life…enjoy every minute of it. A new Fan, Christine Yardley, Pa

  18. Nikira (@nikiraa)

    Wishing you the best, very interesting projects.

  19. theartistonetheroad

    Good for you and congrats on your decision! I’m sure you’ll have much success. Sounds like a wonderful adventure. Cheers to a new exciting life!

  20. Carol

    Wow, Danny! This sounds great! I know you’ll tell us of all you’re doing – I’m looking forward to your adventures, too!
    The way to do it is to go and do it. :)

  21. Joy Corcoran

    I’m so glad for you I think we’ll all benefit from this new chapter in your life. You may feel unmoored for a bit, though. Something about the routine of a job keeps you grounded. I always loved that part of the work-a-day world, but had to quit working because of health problems. You might over-commit to creative endeavors at first, but, I bet within a year you’ll be sailing towards your most creative waters.

  22. Nuno

    My best wishes for that new chapter in your life! And thanks for sharing those thoughts with us.

  23. shebicycles

    Wonderful move – and I am fully confident it is the absolutely best one one. I share the sentiment of being so happy for you and the new roads you will travel, the new creations, the words, the pictures …. On a personal level, thank you for everything your books and posts have taught me and the countless ways they have inspired me – and I can’t wait to see the wonderful things yet to come. Congrats!

  24. Gabriela Sampson

    Good luck in your new adventure, Danny! We , the followers, will be along your new trail, as and when you wish to reveal where you are and what you do and your thoughts… You actually DO what the rest of us only dreams about…you are really embracing life!
    Best thoughts and wishes

  25. Nancy Vogt

    Good for you. You are doing what most of wish we could – but we will all benefit from your courage, your freedom, and your dreams. Thank you.

  26. Katie Metheny

    It sounds like the time is right! Happy Trails! Enjoy opening new doors and windows. Look around corners with enthusiasm! Again….. Happy Trails!

  27. cathy holtom

    Good for you, hope you enjoy every minute of your new life!

  28. Rita

    I knew this was coming from your original allusion a month or two ago, and then more certainly during the recent monkey essays. Sure–it’s scary, but it is obviously TIME. I say Go For It. You’ll be fine. The transition is part of the adventure … you now WON’T be in the same rut every day. Hooray! Have fun and high five!

  29. Alexa

    Delighted for you! And I will be signing up for that online class asap :). Hoping for wonderfully happy things for you in your new life,

  30. SiverBlack

    Rock on! I can’t wait to see what awesome stuff you’re working on.

  31. Nicoleta

    You really know how to make an impact! First line in my e-mail (I get automatically when you have a new post) it shock me!!
    As I was reading I got tears in my eyes…it is soooo great, so generous from you to make us “witness” of the moments of your life …I can visual you writing this in your nice office , looking at the clock for the last time, etc…
    I see it like a sacrifice from you, so we can get so much more of Danny Gregory from now on!!!

    I know I’m not the only one that was “touch
    “by your magic (writings, videos and drawings)
    Thank you very much!!!

  32. carolleebeckx

    Oh good luck Danny. You will look back and know that this was one of the best decisions you have ever made. Change is so energising, you will wish you did this years ago.

  33. msmeaton2013Marjory

    Congratulations Danny! I started drawing last year with my husbands encouragement . he loaned me two books, Every Day Matters and The Creative License.He said “draw what you see”.
    About the time I started drawing a good friend of mine who always encouraged me and believed in my creativity was diagnosed with terminal cancer. She died two months later, she was a wonderful artist and would have asked me why I waited so long! Her goodbye letter to me was a drawing of a beach with the inscription “Life’s a Beach!” She thanked me in a poem for being her friend and the fun we had. So Danny Life’s a beach! Have fun !

  34. Sonja Frey

    JEALOUS!!! remember – open heart, open mind

  35. catagonia12

    There’s a book called “Living Your Unlived Life”, since I retired two years ago, that’s what I’ve been doing. Thanks to your wonderful books & blog, I have had lots of encouragement to pursue my unlived (creative) life. I’m glad you are pursuing yours!

  36. christinenorabehrens

    Danny, You are always full of wondeful surprises! I’ve been following your blog in silence for a while now, but I just have to write and let you know how inspiring your leap is. I’m getting ready to leap too and I look forward to hearing about your new adventures.

  37. Virginia Hanley

    Happy trails!

  38. Mikey

    I have so enjoyed reading your daily thoughts and prespectives on art, and other things. These past few days the monkey writing is especially helpful and inspiring for me, but all your writing is inspiring.

    Best wishes on your new adventures, may you bask in the joy and light of following your heart and dreams.

  39. Annde

    I AM SOOoOooOooo Happy for you!
    Go Danny Go!
    Love Annde

  40. Jacky

    Congratulations Danny. You are an inspiration to us all. We should follow you and be your Leaps Peeps

  41. gypsysnail

    Holy oaks! :-) you have just inspired me to do the same. Love your work Danny, everything you do is with passion. I enjoy your blogs and art

  42. Suzy

    That is awesome news Danny! Congratulations on taking the leap of faith into your new life and adventures, I’ll be right here applauding you each step of the way! Looking forward to every adventure you share. God Bless.

  43. Linda Kelly

    Congratulations on your decision, Danny! How exciting (and a little scary, I’m sure) to be walking full scale ahead into new adventures. I wish you the best of luck, and can’t wait to hear about where your path leads. And, sign me up for that on-line class, my friend!

  44. Lynn Cohen

    Your life jounney seems to be flowing easily through a new door on to new exciting adventures; I wish you well on this newest of paths, in relationship, creativity, geography, teaching, etc. I feel your excitement! Mazol Tov!

  45. pamandherart

    saw this one coming. Congrats on having the courage to follow through…..a lot of us don’t have that …yet!

  46. bettymingliu

    Congrats, Danny! I totally relate because I quit my job in May to work on my first book project, with plans to self-publish and…illustrate it myself! Sitting here now at my big dining room table, surrounded by pencils, drawing pads, tubes of watercolor and sumi ink. The table faces my deck. Screen doors are open and I can hear the crickets, hear/feel the breeze. Total bliss. Hope to never punch a clock again! Good luck to you and looking forward to your next book. :)

  47. Michael C. Kalman

    It takes a lot of guts to do what you are doing. Bravo! I wish you good luck and happiness in this exciting next chapter of your life.

  48. Holly Kreag

    How exciting, Danny! Best wishes on your new adventure. May every moment be enjoyable!

  49. Kathy Kelly

    Tears were welling up in my eyes as I read your post, Danny. For some reason, you have gotten under my skin these past few months. I think it has to do with some kind of distilled goodness in you. Kathy

  50. AmyN

    Congratulations, Danny! All that you’ve put out into the world for all of us has paid off. How exciting! I can’t wait to see what else you’ve got for us. And yourself. Enjoy!

  51. Anna Cull

    Congratulations! Enjoy your adventure : )

  52. Elsbeth McLeod

    Wow, Danny… I couldn’t be happier for you!! You are going to never ever regret this decision, I’m thinking. Well, maybe you’ll have your moments, but overall, I think not only will you not look back, but your delightful son will remember all his life the brave moment you claimed your life and followed your passion. I’ve had ten years out of my adult life I worked in the publishing miasma (divorced, single mom), but most of my life I made a living either painting or sculpting. I wouldn’t change a moment of it. And thanks to you, at the age of 60, I’m inspired about publishing/illustrating my own work. AWESOME NEW FRIGGIN’ CHAPTERS!!! YAY!!

  53. Debbie

    For all of us who dream of the opportunity, thank you. Thank you for being so brave, for knowing what you want and being willing to do it, and for allowing us to travel along with you. You have just brightned my day!

  54. monbaum

    Oh wow, that is quite a leap, but I am sure you will never regret it! I am even a little jealous. Ok, a lot ;-) all the best for all that is to come!

  55. Chris

    Good luck – it sounds like a great thing to do!!
    If you have not done it until now, then the time wasn’t right. Now you yourself feel it’s time for a change – now the time is perfect!

  56. Caatje

    That is so cool! Wishing you the best of times and looking forward to see what your future brings. Good luck!

  57. Cathy Tenzo

    Congratulations! Your work has inspired me so much over the years. I’m glad you’re taking this step for yourself and your family, and also looking forward to any new books and things this helps to enable.

  58. Matthias

    Danny, congratulations for this important leap! I’m really happy for you! :-)
    To be honest:
    New Year 2012 I’ve startet to read your very inspiring book: “The Creative License” -
    This book changed my life in many ways, it was very encouraging for me, but then I realized, that you were employed at the agency and I thought:
    “Oh my god, how can this talented and inspired man stand this?” ;-)

    Now, all things are fine!
    Keep on drawing…
    - Matthias

    P.S. “Bi-coasted”… Los Angeles – New York
    how wonderful! I’m a little bit jealous …
    Since decades, I’m “dreaming of California”…
    Maybe, one fine day, I’m able to make this dream come true… ;-)

  59. pamiejane

    Well done and good luck!

  60. Marisa

    Congratulations!! You had me at “online class.”

  61. Cecile Somers

    FANTASTICO! What a leap! Cheering you on from my advertising agency office window seat in Luxembourg.

    I think it was Susan Sontag who said “Security over freedom is a deplorable choice.”

    And now I can hear Cat Stevens sing “So if you want to be free, be free…”

    Well done, you. Here’s to all the goodness coming your and our way soon. Bring on da monkies, et alors on danse!

  62. Beth Berman

    One of my favorite quote:
    “Leap fearlessly into the void,
    What awaits is the creative power of the unknown.”
    Have a wonderful adventure!!

  63. Karen

    An online course????? I’m in!!
    All the best Danny!!

  64. cynthiamorris

    This is so exciting! The gifts awaiting you in your new creative adventure will be pure delight.

    Have a blast going bi-coastal. I can’t wait to vicariously enjoy your adventures.

  65. Peggy

    Frankly, I am not surprised that the man who inspires so many, beginning with Creative License, has taken his own advice to “just do it”. Thanks for letting us follow along. Can’t wait to see where you’ll go.

  66. Valerie Brown

    I also sensed (knew) this was coming. Welcome to the other side (ha, ha), Danny.

    It sounds like your leap is well thought out and that you have lots of projects to sustain you and keep you moving forward. I am also very interested to see what the on line course will entail!

    A few years ago I was pushed off the cliff – and so started my creative journey/self employment. Unfortunately, since it was unexpected, I am starting from scratch. However, I really do appreciate being my own boss and making my art to my schedule.

    All the best on your new adventures!

  67. roosnans

    you know your monkeys well, so I think you’ll be just fine! So, enjoy your leap, good luck and have fun fun fun!

    ps: the Rijksmuseum and the Van Goghmuseum in Amsterdam are re-opened after years of being closed and rebuilding!

    • dannygregory

      I’ll be in Amsterdam in November!

      • roosnans

        Have a really nice time! Enjoy!

        And if you like old towns, Utrecht is worth a visit too!

        • Andie

          Andie/ The Netherlands,
          Danny I wish you all the luck and enjoy! Because of you and your books, I was in Barcelona last june with the Urban sketchers. And this was fantastic.
          So if you visited the Netherlands in november don’t forget Rotterdam! Old and new architecture in once. .

  68. Mim Stella

    Congratulations on making the “leap”. you’ll love it!

  69. miatagrrl

    Congrats on making the leap, Danny! I made a similar leap 10 years ago and have never, ever looked back. You deserve this! And I look forward to seeing the results of whatever your trails lead you to.

    - Tina

  70. Dawn

    Congratulations! I’m sure there are many of us who hope to follow in your footsteps one day. Best wishes for a wonderful, exciting future! I can’t wait for the online class!

  71. Kooky Makes

    Congratulations Danny, may your new life bring you even more joy & light and all that’s bright.

  72. Nita

    This is wonderful news! Both for your new adventures and for all of us out here, who will benefit from your new endeavors! Hooray!

  73. Laura (@Bookworm)

    Congratulations and best wishes!

  74. Marjory

    Congratulations Danny ! I started drawing last summer. My husband gave me Every Day Matters and The Creative License to get me started encouraging me to “draw what you see” I started drawing about the same time a very good friend was diagnosed with terminal cancer,she died two months later and kept her illness to her self. She was such a creative artist, and always encouraged me, believing in me when I didn’t. Your books and her spirit,with my husbands’s encouragement have helped me a lot.I almost considered your workshop in May! Good luck on your quest. I hope to start my own quest someday.
    We are visiting New York next month first time for me!

  75. Mary Ellen Bratu, Psy.D.

    All the best to you, Danny, in what’s sure to be the next rich chapter in your life. I’ve followed your work for many years, drawn to your bravery, unbridled talent, and willingness to live out loud. I’m excited for you and look forward to hearing how it’s all unfolding–and happy to hear it’ll include more books. I myself left advertising so many years ago to pursue work in clinical psychology but I’m wondering whether you, too, feel a degree of indebtedness to that industry for showing how powerful and vital a force creativity can be. I’ve used your books in my private practice work, with clients who’ve got creative potential but don’t know what to do with it and others who struggle with the tyranny of perfection. And, of course, with clients who are coping with painful loss. Know that your work has helped me to be more effective in mine. Cheers to you, many, many thanks and all good things on your road ahead.

  76. Loretta

    This is fantastic news! I am so happy for you (and a wee jealous!). Can’t wait to see all you!

  77. Cheryl

    It just feels right. Isn’t this how you started out as a little boy? Now you get to call the shots!! Best of luck in the adventure of your life. Just promise that you will let the rest of us tag along now and then.

  78. Patti

    Free???? You are now working for all of us!!!!! ;)
    Now seriously: Danny I wish you all the best, you deserve it! You can jump and we all will hold you: I sure will do your on-line course and keep on buying and reading and recommending to everyone I know your books. Good Luck!!!

  79. Emie

    Good Luck!!!! Can’t wait for your on-line class!!!!!!

  80. stacey

    i am working backwards…found you through your publishing of andrea joseph whose work i very much enjoy. have read your books in reverse (travel journals, life journals and now EDM). will enjoy being in your class online. thanks for the inspiration and hope the monkey gets sick on planes. good luck.

  81. eSeN

    Yay! I’m so happy for you!! You can ‘hear’ the joy in your post :)

  82. Diem

    Amazing news! Congratulations, Danny! See you in class.

  83. Joe Nevin

    ‘And in the end the love you take is equal to the love you make.’

    The comments above are testament to how much you’ve given.

    All the best


  84. Kimberlee Soule

    we were just looking at one of your books the other night and saying “surely he could leave his job and devote more time to this…” :) Were your ears ringing? Blessings on the next stage of your journey.

  85. crispmind

    you knew that journaling can change your life :-)

  86. Lynn

    What wonderful news. Let’s see what you can do with the Grand Canyon! (I’m serious.)

  87. Britta

    “Ease my Troubles, that’s what you do…”
    Thanks for all the never ending Inspiration and
    All the best for you, dear Danny!
    I love your books, your Blog is part of my week and I’m thrilled looking forward to hopefully good good good news from you!
    You’ve done right!

    LIVE IS!

  88. Rosie

    What do they say – leap and the net will appear.. Sounds like youve been weaving your net for a while, and its ready… Good on you Danny and thanks for sharing your delight and wonder with us all. Trust and wonder, dance through and acknowledge and celebrate it all!!

  89. Andres Lafe

    Best of luck!

  90. Pam Perry

    I too thought this was coming by some of the things you talked about at Rowe.
    If your upcoming classes, talks etc. are half as good as that workshop, you’ll have
    no problems being out on your own. And you’ll have more time to write more books and blog
    entries to be an even more influential inspiration to all of us. Good luck, we’ll be watching
    and routing for you.

  91. Joan

    Couldn’t be happier for you! And an online class for us???!!!! Yipee! I’ve followed you for years, read all your books 2-3 times. Followed you on your journey with Jack & Patti. Now Jack’s all grown up and on his way to his own adventures. You couldn’t time this any better. Good on you for taking the leap.

  92. Andy Casillas Hein

    Having recently “retired” myself, I know the new freedom you’re going to feel. It’s wonderful and a huge breath of fresh air entering your brain. Energy will skyrocket and ideas will flow. Be ready for it!

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