From Pit to Perch: The Journey of the Successful, Highly-Sensitive Entrepreneur.

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bali outdoor office

I admit that I’m biased.

We all learn best from experience, yet any experiential learning is only ever anecdotal. Still, I believe that the same lessons that transformed my life from relentless suffering into a sweet ebb and flow of abundance and joy can do something similar for many others. Perhaps you.

If you are someone who identifies as “highly sensitive” or “introverted,” and who has wondered how you’re ever going to achieve the career success you’ve longed for without losing your mind, then I write for you. I share my “journey to success” with you in the hope that you may glean something from it you can apply in your own life, and see transformative results.

A little back story:

I started life as a really poor kid in a really big family. I only have three siblings, but we had four generations living together. And it was only a three bedroom house.

There was a constant bustle in the household, and I found it all overwhelming.

The stories my family tell of me are finding me hiding in cabinets, under tables or behind doors. They tell the stories as if they are charming, but really it just reminds me of that feeling of wanting to find some small quiet place in which I would feel relaxed, having shut the endless cacophony of the world out for even a little while.

In my 20s I moved to San Francisco and, being constantly broke, had to share apartments with other 20-somethings. It never lasted long, because even having my own room, I just couldn’t manage the amount of social contact needed to get my housemates to understand I didn’t dislike them simply because I avoided them so much.

I just needed 95% of my time to be spent alone in order to maintain my fragile grip on emotional, functional competency. I had to be able to go to work each day, and that meant I needed to be alone in my room as much of every evening as possible.

And then there was work. It was brutal. The commute… so many people. The time spent in the cubicle—well, at least I usually had a cubicle. I never lasted more than a couple weeks in any situation where there was an open floor plan. Not that I lasted long in any job at all. I was 36 years old before I hit my first two year mark in any job, and usually I couldn’t manage much past six months.

Obviously, with so little consistency in any position, it wasn’t exactly a great foundation for a profitable career. I was smart, so learned new jobs quickly, but I was always starting from entry level, even after getting an MA in Counseling Psychology.

The shift:

At the age of 33, I decided to sell all my possessions and move to Bali, Indonesia. I didn’t even know where in Bali I was going to live. At the airport I picked the cheapest taxi destination off the board and told the booth agent I would like a ticket to that city, and he refused to sell me the ticket. He claimed I wouldn’t find any place to stay there. We argued a bit and then I gave in and asked him where he would sell me a ticket to. The city he picked wound up being the city I spent the next year living in.

For the first four months I did little beyond sitting out on my deck watching the sky.

It was as if I was letting all the stress and overwhelm of my entire lifetime melt away. I had a household helper (a pembantu) who did the cooking, shopping, laundry and cleaning, so I was for the first time secure in my physical survival without feeling like I needed to be dancing as fast as I could to hold it all together. For the first time in my life, I truly relaxed.

Around the same time I was introduced to ideas about spiritual manifestation. I had met a trance channel not long before deciding to move to Bali, and had gone to Bali with one of my intentions being to learn how to channel verbally. I’d been able to do so with automatic writing for many years, but was always unable to translate the impulses I got into spoken word. The act of speaking seemed to always break the connection.

Putting it all together, the practice of channeling each day, the book on manifestation with spiritual methods I was reading, and the ample time relaxing in the arms of nature… something in me shifted. With that inner shift, my outer life began to shift too.

Everything I had struggled so hard to try to achieve before that, suddenly started walking up and laying itself across my lap. After about four months I had my fill of my sky gazing, so I started going into town a few times a week. Mostly I would just hang out in restaurants for westerners for many hours at a time. I’d often sit there through three meals and a movie.

Within the chance encounters I had on those excursions, I began building a network of people who knew the subjects that interested me, and who had connections to make things happen I had never experienced. Many of them started offering me “once in a lifetime” opportunities, which I eagerly accepted from my newfound inner state of peace and strength.

Flash forward to today: 

The path from there to here has been eventful. In the intervening years I’ve written two books, spearheaded the building of a land trust community for poor Native Hawaiians, taught meditation to incarcerated teenagers, built up two successful businesses, and virtually “retired” in my 40s, given that I’m now completely supported by passive income.

While there are many lessons that could be learned from my story, my chief takeaways have been:

>>> Learn how to let go; let things come to you from a place of security instead of chasing them from a place of need.

>>> Do what you need to do to create a sanctuary for yourself, even if only for a few months.

>>> Don’t settle for poverty even if you come from poverty. Always reach for more and know that you can create whatever you can imagine and believe.

>>> Apply spiritual law to mundane concerns. Don’t separate anything from what you consider “sacred,” not even the making of money.

>>> Don’t require that the work you do to keep your body alive (fed, housed, etc.) has to be the same work you do to make your greatest contributions to the world. It may be, but that requirement can keep you paralyzed during the many years you are really just acquiring the skills you will need to have your impact.

>>> Think passive income! Always be asking yourself, “How can I do this in a way that I invest time/money now, then am repaid many times later without much further effort?” You must decouple effort from earnings if you will ever be truly free of the monkey on your back of needing to be “making a living.”

While I realize that not all of this advice will fit everyone’s needs, I truly believe that for most sensitive or introverted people, this is the surest path to peace, abundance, and fulfillment. But don’t take my word for it.

Experiment with these ideas in your life, then come back and tell me your stories. I really want to know. You see, once you climb out of the pit of despair, there is nothing you want more than to light a path for others to take to join you.



8 Steps for Living an Epic Life.


Author: Indigo Ocean Dutton

Editor: Catherine Monkman

Photo: Michael Coghlan/Flickr

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Indigo Ocean Dutton

Indigo Ocean Dutton spends most of her time enjoying nature with her dog, Magic, volunteering with local youths, baking pies to share with neighbors, and growing just a bit more of her own food each passing year. Her BA is from Brown University and her MA is from the CA Institute of Integral Studies. You can take her latest free course on the Freedom Business Launchpad or find out more about her custom “business development as part of spiritual development” work with small business owners at Awaken Business Consulting.

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anonymous May 24, 2015 4:35am

I live in a town of 65 people in the dense forest. I am an introvert who is sensitive to noise and smells, and am at home in the woods. It's never completely quiet because nature can be very noisy, but it's sound and stimulation I enjoy. I couldn't go back to city life, it would be the end of me. I'm glad to have found your blog through Growing Your Blog and will subscribe through Feedly.

    anonymous May 25, 2015 11:55am

    You are very fortunate! You live in a setting that can be like a permanent retreat, or sanctuary. And you are wise enough to savor it instead of resisting or regretting it. Glad you found your way to this article.

anonymous May 24, 2015 4:20am

What a fantastic post full of inspirational soul-food!

    anonymous May 25, 2015 11:54am

    I'm so glad you liked it! Thanks for your comment. I love that metaphor. Yes, nourishing the spirit. That's the idea.

anonymous May 24, 2015 1:38am

This a wonderful post with lots of wisdom in its brevity. Thanks for sharing your lessons with all of us!

    anonymous May 25, 2015 11:53am

    You are most welcome, Ben. In the sharing there is another leg in the journey of growth and healing for us all, myself included.

anonymous May 23, 2015 11:31pm

This is great. I admire your attitude about life.

anonymous May 23, 2015 2:00pm

Indigo, thank you for sharing your story! Whenever any one of us who is HSP and introvert steps up to share their journey, it encourages us all! I'm glad that you have been able to find a rhythm to your life that works well for you. Many blessings!

    anonymous May 25, 2015 11:52am

    Thank you, Embrolic. I'm glad to be able to share something that encourages others, as I was once encouraged myself. We are leaves in one family tree.

anonymous May 23, 2015 12:19pm

Wow! You've led an interesting life! I would love to just pick up and move to another country!

    anonymous May 25, 2015 11:51am

    Then do! Maybe not now, depending on your responsibilities to others, but at some point. It has a big effect in many people's lives, and likely would in yours too.

anonymous May 21, 2015 9:43pm

Thank you for helping me to better comprehend the experience of a highly introverted extended family member. Thank you for also helping me to open a little more to flowing fully with life. Or maybe that should be opening space for life to flow fully in me?

    anonymous May 22, 2015 10:54am

    Glad to hear it. Your family member will now have an ally who understands his/her needs.

    Regarding flowing, it is really both. Try this: Imagine a beautiful, loving light that permeates and surrounds you. Really feel it there…

    Once that feeling is clear…

    Allow your awareness to relax into that light, recognizing it as yourself, with all boundaries between you and it dissolving into light….

    That's what flows.

anonymous May 21, 2015 7:31pm

I so appreciate your strength in providing a peek into your life journey, especially the "learning" stages where oftentimes the pain is real and too often withheld from public view. To then transform emotional struggle and life challenge into bliss and life success…gets a big WOW and woohoo from me! Your story exemplifies human spiritual perseverance and trust in personal evolution. I enjoy your soothing writing style and look forward to future posts!

    anonymous May 22, 2015 10:49am

    Thanks so much for your kind words. You actually brought tears to my eyes. Yes, sometimes all we can do is to persevere. Yet if we remained committed to our longing to be happy, and responsive to the guidance of spirit in creating that happiness, the perfect bliss of our true nature is indeed within our reach.

anonymous May 21, 2015 6:25pm

Hi Indigo, thank you so much for sharing your story so freely with the world. I am in that '9-to-5' office cycle and have been for 12 years now and I often think of escaping – I have lost my passion for painting (which used to be my craving) and now I love to immerse myself in Ashtanga yoga when I'm not at work. Your article has reminded me that there is no need to force the entrepreneurial skill, the 'need' as you said. I'd love to get out of the office cycle one day but perhaps surrendering instead of 'needing' (eg money) is the better way to go. Thank you for the inspiration. Namaste

    anonymous May 22, 2015 10:42am

    Your settling into the perfection of your current moment is beautiful. It is from that place that perfection will be made more and more apparent in your outer circumstances.

anonymous May 21, 2015 6:15pm

Awesome article! Thanks for the inspiration – seems I always receive the message my spirit is seeking when I open up and look around. Am currently letting go of a long term job to pursue a more independent path and your words echo the voice in my own heart. Blessings to you!!

    anonymous May 22, 2015 10:33am

    I'm so glad it resonated with you, Scott. Isn't it wonderful how once we tune into spirit and start following its guidance, it starts sending us more and more of it? It's as if it says, "Well if you'd really like some help, then here you go." Lovin' the ride!

anonymous May 21, 2015 10:14am

thx. I have the same issues & now I understand better why. thank u.

    anonymous May 21, 2015 12:49pm

    Sometimes all it takes is realizing we aren't alone in this. "Others have faced this and not only survived, but thrived, and I can to." If I have helped you feel that way, this entire article has found its purpose.

anonymous May 21, 2015 10:14am

To all of you who have asked about the free course, you can access it by clicking on my name beside this comment or through the link in the bio. It was originally a webinar, but I didn't like the stress of doing webinars, so I converted the one I did into a free course people can take anytime. It does have more of a webinar than course feel because of that though. People were really enthusiastic after the live event, so I'm confident that despite it's origins, it is still a good course that inspires and instructs. I have other courses after that to help guide and support folks as they apply what is taught in that free one, but really what you need to do is just that. Then there is just the matter of the doing.

The entire journey can be an incredibly fun one once you learn to let it be. That learning is simple, but not easy. There is so much we have to first unlearn. But you have my support for that, and the support of many others who have faced similar challenges, but done it anyway. You can too. Come and join us! This really is meant to be a joy ride.

anonymous May 21, 2015 9:45am

Great article!

anonymous May 21, 2015 8:07am

Thanks for the article! Great information to read now, as I'm ready for something to happen! I left my corporate career when I become a mother to twin boys after 4 years of infertility. They are now 2-years-old, but I have lost more of myself than I dare to reflect on. I hated working in a corporate environment and know I need to create a business that helps support the family and fuels a feeling of purpose. However, being introverted for so many years has left me with what feels like a very small network. Just trying to figure out what the next step will be!

    anonymous May 21, 2015 12:48pm

    I really hope you'll sign up for the free course. It will give you a lot of idea (8, to be specific) for how you might do that, and in harmony with allowing spirit to really make the path for you. I'm glad you aren't willing to go back to the environment you found unsupportive before. You are in a good position now to experiment with a different way and take the time to build upon a solid foundation. Good luck, and please draw upon my support as much as you need. Consider me your cheerleader.

anonymous May 21, 2015 7:59am

What a wonderful article! This really resonated with me as I also have that urgent need for "alone time" which is very difficult to get between having to be around people at work and with a husband who works from home and is rarely gone. I truly cherish the times he goes on business trips a few times a year. That sounds horrible, like I don't want him around, which is not the case at all. I just want some regular time to myself. Working on creating a sanctuary for myself within our small home to alleviate this problem.

    anonymous May 21, 2015 12:45pm

    That's a good idea. Also consider taking a solo vacation sometime. More and more couples are doing that out of respect for each partner's needs within the relationship. Communication is key. If you convey that it is more about time to connect with yourself than disconnect from him, hopefully he will be supportive of it.

anonymous May 21, 2015 7:44am

Great article! I am inspired to create a passive income so I can live in a beautiful place that is close to nature!

anonymous May 21, 2015 6:42am

Beautiful article Indigo. I left my job 7 years ago do to relentless stress…I'm on my path of least resistance now and learning little by little to follow my bliss. Thank you!

    anonymous May 21, 2015 12:43pm

    I'm so glad to hear you made this change for yourself. So many times people just resign themselves to whatever they have because they are somehow surviving that way. But the way of bliss is so much more fun. Just takes a lot of faith and courage. Congrats for finding both within yourself.

anonymous May 21, 2015 3:28am

Thank you for this article Indigo. I have been very worried about my grandson, who spends most of his time alone. Your article reassured me that it is possible to become successful even if you are an introvert. I will let go now and let him find his own path, in his own way. Very grateful to you. for this timely advice.

    anonymous May 21, 2015 9:59am

    Yes, Pat. It really is just a different way of relating to life when you restore energy while alone and spend it while with others. Your grandson is just doing what he needs to do to take care of himself. The more you support that, the more easily he can self-manage, because he won't also be dealing with the weight of feeling he is worrying people or letting them down. Have faith in him, and keep sending him "vision prayers." See him as happy and successful, living life his own quiet way. Think of him like that whenever you think of him. In doing this, you'll be sending him "psychic invitations" to create that life for himself in the light of your love.

anonymous May 21, 2015 3:21am

It seems contradictory to tell people to "not settle for poverty", yet talk about security and need. I've been applying for jobs for almost 2 years now with no success. I'm almost at the brink of suicide. Life seems utterly worthless to me. Nothing seems to happen, there's no development in my outer reality. I just really want that golden opportunity to get that dream job to pay off my debt. It's quite a simple wish actually. Nothing mind-exploding. Just a simple man's simple wish. Maybe there's a reason I have created this to myself, but I can honestly tell that I'm not enjoying it.

There will be no worries after death.

    anonymous May 21, 2015 9:39am

    I felt this way sooo many times for sooo many years! I actually attempted suicide was I was only 9 years old. Thankfully I sucked at suicide, and then I got old enough that I realized how great an impact my leaving would have on those who loved me, so that put an end to that "way out of suffering." Eventually I also realized that I didn't really want my life to end, just my suffering.

    It took a long time and a lot of spiritual and emotional to get to the point that I could even see a reason to sell all I had and moving to a place I could live without the pressure of working for survival. Before that I would have thought of that as just another waste of time within my hopeless life.

    Thankfully I immersed myself in spiritual teachings that gave me experiences of happiness even while I was in the midst of despair. Then instead of focusing on the despair, I focused as much as possible on those moments of good feeling. I really milked them for all they were worth. Instead of ruminating on all that was wrong and the many painful experiences of each day, I pushed those memories out of my mind and kept reliving each good feeling moment. In this way I began building new momentum for myself.

    The painful situations continued for a long time. I had a lot of momentum behind that life, decades. But little by little, the good took up more of my life and the bad less.

    Even now, life is a mix, but there is far more good than bad. Still, each day I work on starting my day feeling good, even if I have to lie in bed just feeling how good it feels to be warm and cozy and not get up until I can get a worried thought that came to mind off my mind. And then I meditate first thing, to further train my mind to be able to focus where I put it and not get lost in troubling thoughts. This mental training is key, and was also one of my turning points while in Bali, because I had to do it in practicing my channeling.

    And still, all day long, I get "invitations" from life to feel worried or sad about one thing or another, and I have to deliberately decline those invitations, to choose to focus on something that is going right instead. Because I know from experience the power of my mind. I know that I will get more of whatever I focus on, so that it is vital I focus more on what I want than on what I don't want, more on what I like than on what I don't like, more on solutions I intend to see in my life instead of problems that are challenging me now.

    This is a really long answer, but I think you are at an early step in the journey I took, so I want to try to show you what the path can look like in more detail. Bottom line, it begins by your committing yourself to train your mind. Then you must learn to have more faith in what is in your imagination about what you want than you have faith in what is in your current reality, recognizing what you see now as merely the visible echo of thoughts and feelings from your past. Good luck. It really is worth it. You'll see that once you make it to the good part! And then thing what an inspiration you will be to others and the stories you'll have to tell.

anonymous May 21, 2015 1:38am

I feel like I am channeling your path in a way. I can relate so much. I work from home now and am doing writing on the side. I am very sensitive as well and couldn't handle a traditional job. Now, I just need to find my Bali!

    anonymous May 21, 2015 9:27am

    Congrats on making the home-based livelihood work for you. You may find your Bali right where you are, if you can spend enough time in nature. One of the things I was told by a channel before I left for Bali was that I had to learn to let nature love me. At the time I was already enjoying hiking's restorative properties quite a lot, so thought that was what she meant. But then once I got to a certain depth of being there in such a lush and tropical place, it really sank in. It was a different state of being. You see, letting something love you means letting it permeate and shape you. It means letting it become a part of yourself and letting yourself be made different, even as you do the same in return, so that a union occurs. I got to a place where I could actually feel the plants and trees around me as if I was feeling a part of my own body. So I guess I would say, wherever you can learn to let nature love you can be you Bali.

anonymous May 21, 2015 1:32am

This is fantastic Indigo!
I never knew your journey was so wondrous and deep. Now I'm even more in awe of what you have achieved!

    anonymous May 21, 2015 9:23am

    Thank you for your kind words. It has been a challenging journey but I always say, I'm so glad I finally made it to the good part!

anonymous May 21, 2015 1:23am

What an awesome article – your description of cubicle life and getting away really resonated with me. It's something I've considered in the past, but definitely something to re-examine!!

    anonymous May 21, 2015 9:22am

    Oh and I can so see you enjoying the sweetness of life for some extended period. Your genius and natural inspiration would be given wide berth. I can only imagine what would come forth from you afterward to bless this world.

anonymous May 20, 2015 10:25pm

Wonderful easy to read with inspiring mesage and a path to fallow 🙂 Congratulation and thank you for sharing your life story with strangers !

anonymous May 20, 2015 10:00pm

I loved the six advice items at the en; I get that you really know your stuff.

    anonymous May 21, 2015 9:21am

    Thanks, Frank. It took years of not only experiencing it while really trying to learn, but years after that to truly digest what the experiences have taught me. But I'm working on getting better at being able to convey what has become second nature to me by now in a way someone looking at it for the first time might understand.

anonymous May 20, 2015 9:23pm

That's a great article, many points I could relate to, it reminded me how much I like my own private space. Although I grew up in a large house with my own room I still liked to climb into the warm airing cupboard. At 6'4" I don't do that any more. 🙂

    anonymous May 21, 2015 9:20am

    That would take a pretty big cupboard! Thanks for your comment and glad you could relate. Enjoy the journey.

anonymous May 20, 2015 9:17pm

Thank you Indigo for sharing your story. Your story is inspiring!

    anonymous May 21, 2015 9:19am

    You are so welcome! Glad it resonated with you.

anonymous May 20, 2015 9:15pm

Wonderful easy to read with inspiring mesage and a path to fallow 🙂 Congratulation and thank you for sharing your life story with strangers !
And your encouragement to join you in your happy place in life ! It's all possible if we dream big take some steps forward and relax about all!
Life is good if we just allow it to be 🙂

    anonymous May 21, 2015 9:19am

    Your final words really say it all, Elizabeth. Life is good, if we just allow it to be. Yet that isn't what we're taught growing up, so we have to relearn what we were born knowing. And support each other in that relearning journey.

anonymous May 20, 2015 9:15pm

I loved your article, Indigo. SOOOO many times in my life I physically and emotionally 'craved' an escape to some beautiful place, surrounded mostly just by nature, even if only for a week or two to connect with ME and restore, but I never did. I made the mistake of always making others in my life more important than my own needs. I'm impressed that you honored your own needs so well, and that you were so wise and courageous at such a young age. You've inspired me to commit to taking a personal retreat at least once a year, if not more. Thank you so much for sharing your story!

    anonymous May 21, 2015 9:18am

    It means so much to me to read your words. It will make a huge difference in your life if you follow through on this commitment to yourself, even just one year, let alone for some time each year. Think of it as giving your fields some time to lie fallow. Enjoy.

anonymous May 20, 2015 9:08pm

This is a fantastic article and I would love to know more about passive income and your free course.

anonymous May 20, 2015 8:59pm

Inspiring. I was riveted! You got me thinking about passive income…. <3

anonymous May 20, 2015 8:34pm

Great article, Indigo. 🙂 Not as introverted as you are but it was interesting to read that perspective.

    anonymous May 20, 2015 8:52pm

    I'm glad you enjoyed it… and that you aren't as introverted as me! It has it's blessings, but the level of self-care needed can sometimes be extreme. Thankfully there are just as many paths as their are people.

anonymous May 20, 2015 8:15pm

Beautiful article Indigo! Congratulations on making your life exactly what it needs to be for you! Happiness and joy be yours always.

    anonymous May 20, 2015 8:38pm

    Thanks, Christine. I guess that's what inspires me to share my story. I want to encourage more people to take whatever risks or make whatever changes they need to create the life they most want. We really don't have to settle for what we're used to, even if it is all we've ever known.

anonymous May 20, 2015 7:44pm

Great post! I have been contemplating a retreat to a peaceful place. Thank you for the encouragement.

    anonymous May 20, 2015 7:54pm

    It is something that I think everyone should do at least once in their life, even if only for a few months. It provides the outer space that makes it easier to go into an inner space and find what we've always been searching for.

anonymous May 20, 2015 7:36pm

I hope you all really enjoy the article. And please don't be shy about leaving a comment. I've been very much looking forward to chatting with you here.

And btw, the link to Freedom Business Launchpad is broken right now. If you want to enroll in the free course, just type in and you'll see it listed there (or just click on my name with this comment to go to the exact free course page).

Did you ever have a time in your life when you were so completely done with the life you had that you were willing to let it all go for the chance at something more?

    anonymous May 20, 2015 7:55pm

    Link fixed!

    anonymous May 21, 2015 5:51am

    Yes…yes! I was a school librarian for 30 years and have recently retired and decided, like many who retire, to find my authentic self. I had started painting as an artist before I retired and absolutely loved expressing myself this way….long story short, I started painting animals, especially dogs and now I have the beginnings of a successful business ( Thank you for your story…very compelling as it is so true. Life is to be enjoyed, giving back and being grateful for the path you are on….if not, change it up and seek your authenticity by asking and you will hear your inner voice speak. Wonderful story! Keep writing!

      anonymous May 21, 2015 9:16am

      Exactly! Nice to meet a kindred soul.

    anonymous May 21, 2015 8:20am

    What a wonderful Journey ……much love to you.