On Chucking It All and Going On the Road

Ontheroad1 chucking it all


I made a huge change in my life when I was 19 and I left Nebraska to move to Hawaii.

It was the best decision of my life.

Now, over 40 years later, I’m about to make a change that is almost that big.

I’m chucking it all and going on the road.


I’ve spent over 40 years in Hawaii and I have loved living here. I’ve loved making a career here as an artist of the male nude, being able to live in Hawaii and still have collectors all over the world. I especially loved the change I made 3 years ago, when I bought an apartment (my first time as a homeowner) in Waikiki. I loved the apartment, and I loved living in Waikiki! I absolutely loved waking up in the morning and looking out at the ocean, Diamond Head, and the Ala Wai canal, seeing the palm trees sway in the breeze, and knowing that I lived in the most beautiful and comfortable place in the world.
It was perfect!
Yeah, PERFECT…for a while.
But paying a big mortgage every month, not being able to travel much because of that mortgage, and living in a place that feels like my PERMANENT home in a way a rental never does, has had an effect on me. As much as I’ve loved living in this apartment, over the past year or so I’ve begun to feel a bit like a prisoner.


I felt like I was chained to this apartment and its comforts (not to mention Hawaii and its comforts) and I kept hearing this very reasonable-sounding voice saying, okay, now it’s time to just accept it, you’re over 60 now, you’re slowing down, settling down, you’re going to grow old here in this place. Relax and enjoy it…it’s a beautiful place to let your life wind down.



…let my life WIND DOWN??



So here’s what happened.

I was cleaning out a kitchen cupboard one afternoon and I was about to wad up and throw away a months-old issue of the Honolulu Weekly when an article caught my eye.

The story was about a British woman in her mid-40s who is rowing her way around the world. Yes, ROWING. Roz Savage had a mid-life crisis when she realized she had lots of material things and a comfortable relationship and a cushy job, but something was missing. At that point she did something really interesting: she wrote two versions of her own obituary.

In the first obituary she imagined continuing her life as it was going. In the second version, she imagined herself doing something adventurous and living life by her own rules. It was quite an epiphany for her. She wound up deciding to end her marriage and her career and give up all the material things she thought were important. That’s when she came up with the crazy idea of rowing across the Atlantic. (Read the article at the bottom of this page if you like.)

I’m not going to row across the Atlantic. (It’s painful enough flying across it in Coach.) But I have taken her message very much to heart.

Okay, it’s not quite the same. I’ve been living an adventurous life by my own rules for practically my whole life, and I’ve loved it, and I love my career and I will be keeping it. But that story really struck a nerve. I was standing there at my kitchen counter reading the article, thunderstruck. I realized what I HAD to do.


In a matter of about 30 seconds I not only knew I had to go traveling, I knew how I would do it. I would rent out my apartment (let someone ELSE pay my mortgage for awhile!), move my studio into my current office (which actually has plenty of space for it), sell my car and get rid of everything I didn’t need, and take my drawing, painting and photography (and blogging!) on the road. And I would travel for at least one year!

The fact that it took under a minute for me to know exactly how this would be done tells me that on some unconscious level I’d been planning this for awhile. But I hadn’t known it until I read that article.

What struck me with great force was how RIGHT this felt. As soon as the idea of doing this occurred to me, I knew it was already a done deal. It felt so right on so many levels, there was absolutely no question it was my path. I didn’t realize how unhappy and conflicted I’d been feeling until I finally saw my next step, and saw it with crystal clarity. I got so excited I could hardly contain myself, and I’m still feeling that way!

That was a little over two weeks ago. Since then I have contracted with a property management company to handle renting and management of my apartment for at least 1 year; I’ve put my car up for sale; I’m putting together a garage sale to get rid of everything; i’ve cancelled the cable, car insurance, and a dozen other things I had taken for granted and now feel lighter for having cut off; and the movers are coming day after tomorrow to move my studio into my office.

I’ll be flying to Los Angeles around June 30 (give or take a few days either way) to move in with my friend Gina for a few days while I decompress and start planning the next year (or more) of globetrotting.

Although I’m not going to plan TOO much. I’m excited by the prospect of making it up as I go along.

I love the fact that I’ll be free to travel the world yet I get to keep my gorgeous Waikiki apartment…kind of putting it on reserve until some future time when I’m ready to move back in. This is a mix of liberation and stability that really appeals to me.

I’ll have my studio all set up in my office so that whenever I’m in Hawaii (I plan to come back and check in every 2 or 3 months—where I’ll stay I don’t know yet but that will fall into place) I’ll be able to spend some time painting in a fully equipped studio. But most of the time I’ll be drawing, and photographing, wherever in the world I happen to be.

And I’m inviting you along for the ride, in a way. I’ll be updating you regularly on my adventures via this blog. And of course you’ll continue to see my new art popping up on my fine-art website, www.douglassimonson.com, and new models and photo shoots appearing in new entries right here on this blog.

Don’t hesitate to comment on any of this as we go. I’ve always enjoyed your comments on this Artist’s Diary blog, and appreciated them. Now I’ll appreciate them even more as you give me your feedback on where I’m going and what I’m doing and your suggestions on where I should go next, and what I should do when I’m there! I love the fact that I’ll be traveling on my own, but I’ll never be alone.

As Buzz Lightyear would say, “To infinity…and beyond!”

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25 replies on “On Chucking It All and Going On the Road

    • wendy hickey

      Dear Douglas, I have been back in Hawaii for 4 months, couldn’t keep away. I would love to catch up before you go on your adventure, I was in the same frame of mind 20 years ago so know how you feel,My phone number is 808 3586249 I am living in Diamond head so can make it to star bucks in 10 mins, Australia maybe on your list?? Aloha till we meet Wendy Slaa

  • Chris K. Camarillo

    interesting… can’t wait to see the new models and course of your artistic direction cued by your jaunts abroad. each artist i have known breaks the comfort zone of their own existence because of constraints imagined or real, hope you have a safe and wonderful adventure.

  • ardyth

    hey doug! good for you!! i have done this. I left hawaii Oct 1 2010 and I’m still going! my plan is for a year too!
    I’ve been from florida to calif and oodles of great spots in between. for now i’m stick with the usa…
    it’s so fun and amazing! my advice: travel as lightly as possible. and HAVE A GREAT TIME NO MATTER WHAT/WHERE OR WHO!

    bon voyage! and take you aloha EVERYWHERE! ardyth

  • Ken Sentner

    Hey Douglas, good on ya! You can’t help but win in this adventure; you’ll find new inspiration and perspective that only travel can bring, and your work and life will be the better for it.

  • kelly

    It’s all coming together, isn’t it? I’m excited for you! Can’t wait to hear your stories and see how they come through on canvas.

    I get to see you during your travels, right?

    WIth love from your little sister,

  • Kalei Lyman

    Hey Doug!
    This is totally awesome. What an inspiriation!
    If I had the balls to do what you are doing, there is one thing I wanna do.
    I’d love to see the aurora borealis upclose and personal. I’ve never seen it in person, and would love to experience this phenomina. Seeing mother nature’s version of club lighting would be unreal. Of course, the icing on the cake would be to make mad passionate love beneath a blanket of stars lit up in hues of green and blue… but that’s another story…
    Good luck to you!
    I’ve never been one to blog or follow blogs, but like I said, you’re an inspiration.
    I’ll be checking in on you every now and again.
    A hui hou. Aloha!

  • espy

    Great blog. Great inspirational article. Steph, thanks for posting this on your FB page. After 7 years in HNL, I am at a similar crossroads in my life and welcome the chance to experience all of these new adventures with Doug. Lets me know I’m not crazy or alone in this. Can’t wait to read more.

  • Eduardo Hernandez

    Inspirational. Please let’s get a drink to catch up if you’re in the Palm Springs area @ summer/fall 2011.

  • Kelli

    I am so happy for you….please keep my updated on your itinerary so that perhaps I might join you in one of your adventures! You’ve been such an inspiration to me, and I wish you all the best….if you need a few recommendations in Spain/Amsterdam/Ibiza/Rome, I have some great new friends there that would be wonderful hosts!!! xoxoxo

  • Angela Treat Lyon

    This is so awesome – I’m so very excited for you! Do we have to do anything extra in order to get your posts? Or will you just continue to email us as usual – I don’t want to miss one nano-second!

    And you – well, I was going to order you and say you better call me, but we both know how well you respond to orders! Ha! So – Plizz, call me once in a while! We can keep each other on track for writing our own stories!

    much much love –

  • Vic

    I look forward to some awesome paintings inspired by all the lovely souls you will meet. If you come to Vancouver Canada recall Vic from Hong Kong ( have 2 of your paintings ) you are welcome to stay with us we have a guest room and a lovely ” as close as it gets Hawaiian” garden 🙂 Travel safe ..but then knowing you …I think you’ll be off more likely to southern shores ..Safe journey.

  • Lil Tom

    Writing your own obituaries is a wonderful tool. I’ve often wished someone would hypnotize me to believe I had six months to live–I wonder what I would do. (The lesson, of course, that that’s the way we should be living our lives anyway seems trite, but there it is…and as that sage Clint Eastwood said once in a movie, “Tomorrow is promised to no one.”) Happy trails, dood. As someone who loves and misses Hawaii and yet yearns to chuck it all and see the world, I envy you.
    Lil Tom–San Diego

  • Tanya Hall

    Once again so excited for you Doug….just go for it….know with your energy, vibe and personality that things will work out as they are meant to and that the universe will look after you! I will keep updated on your wonderfully written blog….thanks for sharing!
    Keep living, loving and shining…. Namaste Tanya fm Durban, SA

  • Michael Lee

    Hi Doug, great to hear that you are going to do a lot of traveling. What a great way to see the world. I’m sure you will also meet a lot of interesting people and new models to add to your collection. Good luck and if you plan on passing through San Francisco, let me know. Would be nice to see you again.

    Take care,

  • Rodney Washington

    This is freakin awesome Douglas! You’re officially my new hero. I had the pleasure of interviewing you a few years back (I don’t know if you remember) but anyway I’ve always been in awe of you and the courage you’ve already taken to live your life on your terms doing what you truly love.

    This new adventure is just Chapter 2. I know that you’re friends with the talented Kurt Brown so if your travels bring you through LA again I’d love to officially meet in person.

    Rock on and enjoy your journey, I’ll be watching you through the blog.

    All the best


  • Jason Yaris

    Awesome. I’m inspired. Be open to your spiritual guides and this adventure will be fulfilling. I love your work and am excited about the fruit of your transition.

  • Lloyd Luzerne Thoms III, Wilmington, Delaware

    All your friends and associates, all wish you the best of all possible worlds. At 87, my only thought is that I am 67 years out of date. Always remember that Life is Beautiful. We all will follow your adventures with much interest and enthusiasm.


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