Overcoming Shame When You Took a Risk and It Didn’t Work Out

Grieving woman

“Live, travel, adventure, bless, and don’t be sorry.” ~Jack Kerouac

There was no denying it. I had reached a dead-end. A year and a half spent living in a southern town that was simply too small for me; it was time to go. I needed a city, preferably a large one filled with numerous opportunities for a budding young writer.

Ironically, the very day it dawned on me that it was time to move to a metropolitan area, love summoned me. It shouted to me from thousands of miles away, beckoning me to change the course of my travels.

My long distance/Californian boyfriend, the one I designated the great love of my life, declared that he wanted to move in with me—to the very place I had deemed to be a dead-end. He was sick of his hometown. He wanted to come to mine so we could finally be together.

I knew I couldn’t have my cake and eat it too. I had to make a choice. A city would wait for me; I wasn’t so sure love would.

It took only two months of us living together in Deadendsville for him to suggest that we move. I was hoping he would maybe say Chicago or Boston or New York. Instead, he shocked me by saying he wanted to return to his suburban hometown in Northern California.

I knew he wouldn’t go with me to a big city. He had made up his mind. He wanted me to follow him so he could teach me to surf, so we could camp at Big Sur, so we could have our tanned bodies tangled together every night.

A more sensible person might have ignored such a romantic request, favoring sanity and security over things like sunshine, pheromones, and fun. But I, in my reckless abandonment of all that could potentially shield me from making a poor decision, refused to be sensible. I wanted (more than anything) to be true to my wild heart, which in that moment meant chasing after him.

Like magic, the dead end disappeared and I found myself hurtling at 80 mph across the country toward California. I had no plan. No job lined up. No friends. Heck, I had never even been to the state of California, but there I was, road tripping on some lonely desert highway, pledging my allegiance to the west.

At twenty-eight years old, I knew what was expected of me. I was supposed to be at the very least veering toward adulthood, making responsible decisions, preparing for my future.

All of my peers were getting engaged, making down payments on houses, building their careers. Meanwhile, I was on a mad adventure, whizzing past cacti and mountains, feasting on chips and guacamole, in awe of my own defiant behavior.

Sadly, my fiery romance burned out faster than a campfire in a hurricane, which ultimately spelled out all kinds of trouble for me. I had blown through my savings. I had no vehicle for transportation. No clue where the hell I was going. I also had a hole in my heart the size of Texas. I was beyond lost.

Worst of all, shame swarmed all around me. Loved ones reminding me it was my fault for having such a flimsy plan. My own inner voice reminding me that I should have known better.

I felt too old to be this naive, this bad at protecting myself. I could barely get out of bed, and yet I still had the energy to shame myself over and over again for the foolish choice I had made.

Thankfully, my great aunt (whom I barely knew) invited me to stay on her ranch while I licked my wounds in Southern California.

She too had moved to California in her youth for a love that did not last very long. Apparently, many broken-hearted women in my lineage had sought out comfort in her abode. It’s practically a rite of passage.

Never once did my aunt say anything about my poor planning or taste in men. All she said was, “So what if you didn’t have a plan and you ran off with some jerk? You had an adventure. You come from a line of very strong women. You will get through this.”

There it was. Lo and behold, the tiniest taste of the healing elixir my soul was so desperately thirsting for. I vowed to get well again, to build up my strength, to never again let shame bully me into forsaking my heart.

On the long and winding road to recovering my sense of self-worth, this is what I learned…

Sometimes, we do stupid stuff. We leap before we look. We make unsafe bets. We throw caution to the wind. We let lust lead the way.

It is almost guaranteed that when we take those daring leaps, we become students of humility. We learn why skydivers carry parachutes and trapeze artists have safety nets. We come to understand why for better or worse it is smart to set up certain variables that will help cushion our fall.

And yet, in this great hour of learning, if we forget about the love or the excitement that led us to leap from such great heights, we run the risk of inviting shame into our experience.

When we do that, we make ourselves vulnerable to all sorts of nasty pathogens that seek to attack our inspiration, our courage, our joy.

In case you weren’t aware of it, shame is one of fear’s favorite minions. Fear is very impressed by shame’s innate ability to make even the most gifted human being feel like they have nothing to offer.

Fear and shame have been working together since ancient times, and sadly it does not look like they are going to break contract anytime soon. Together, they create much of the propaganda that has folks like you and me believing that we are the world’s shining examples of failure.

The minute we allow shame to start broadcasting in our brains, there is no telling what other forces will join fear’s army of oppression. Regret. Guilt. Hatred. Disgust. All of them are sadistic opportunists who have no other way of gaining power than feeding off of yours. Still, it is tempting, isn’t it, to invite these ambassadors of fear to keep us company when we are feeling down and out?

You must trust that there is nothing pleasant about having your heart raked over the coals. Nor is there anything so wondrous about sitting with your head hung low sputtering out the words “I’m sorry” or “I shouldn’t have” over and over again. It is actually quite dull. Shame, of course, will try to glamorize the whole act of penance.

Try not to be dismayed by the fact that your thrilling moment of flight was followed by an equally epic fall. So what if the drastic descent blew your self-esteem to bits or fractured the very bones of your dearest relationship? It is not personal. It is not your fault. It is just gravity.

Give the situation some time to heal. If you get lonely, call upon humor, but leave shame out of the picture. I can assure you, shame has no desire to see you put yourself back together.

And what about that choir of onlookers that keeps singing the same four words over and over again: We told you so? Tell them it was one hell of a ride. Tell them you would do it all again—broken bones and all.

Whatever mistake you think you made, whatever wrong turn you might have taken, if it was prompted by the desire to expand your capacity to live fully or love and be loved, then you have absolutely nothing to be ashamed of. You need not repent for a thing. So quit condemning your heart. It is likely that it has suffered enough.

Here is the secret that lovers and fools and risk takers and geniuses have been whispering into one another’s ears for centuries: Never listen to the sober ones who refuse to drink from the cup that is inspiration.

But you, who has gulped your way through life, unafraid to pair the sweet with the sour, you know why you answered the call, though it left you a bit bruised and battered. You know why you chose to move in a direction that was both surprising and intended.

Hold onto that knowing. Protect it at all costs. Defend it with your sole existence. It is the medicine you must take to remember that embracing a path full of possibility and adventure is nothing to be ashamed of.

Grieving woman image via Shutterstock

About Michelle Price

Michelle Price is a creative content writer who is most at home among fierce doers and dreamers. A lover of the overlooked, she delights in her role as an observer. Her eyes, being as wide and blue as the ocean is deep, yearn to gaze upon that which is teeming with life. She can be reached at

See a typo, an inaccuracy, or something offensive? Please contact us so we can fix it!
  • This helped identify what I was feeling when letting go: shame and fear. Great post and advice!

  • Erika

    Amazing writing and love the advice. This is exactly what I needed to read.

  • Lindsey M

    I love this, so inspiring and well written. I’m not current struggling with shame but I know so many people who regret what they’ve done instead of accepting and rejoicing over the experiences they did have that shape them. I will be sharing this!

  • BK

    I am 54 years old, I have struggled with shame & self hatred my entire life from as young as I can remember. I grew up in an alcoholic home, suffered with severe anxiety & self conciseness. I became sexually active (hyper sexual) at the age of 10 and leading to drug use at the age of 13 and at 15 with my then girlfriend pregnant. She had a miscarriage and shortly after we broke up. I always found my self very needy for love as I never received it growing up. I graduated high school near the bottom of my class and soon found myself jumping from job to job taking whatever was offered. I worked in several family businesses always feeling that I was behind everyone else and could not figure out what i wanted to do thinking that I really wasn’t all that great at anything. I raced motocross through out this time and actually did ok, but never as good as some of my friends.
    Once, motocross ended. * I was seriously injured and just decided to quit as I felt I could not make a living as a pro again I was not good enough to win. What I did not realize how much not doing something I loved would effect me. I ended up modeling of all things in an effort to help me to become more comfortable with myself. It did just the opposite – again I ended up comparing my efforts and results to others and was just not good enough and now look back at it with embarrassment that I even did it. I eventually ended up addicted to crack cocaine which, lead me to over 8 treatments and 2 suicide attempts. I finally was able to remain sober for almost 21 years now, faithfully married for 20 years and owning a home in Florida.We have 3 successful children. This is the first time I have shared most of my story as I have kept how I really feel hidden. I went through hell to move to our new home this past June and had to switch jobs with in the same company going back to what I was first hired to do over 20 years agowhich I really do not enjoy, but make good money and do not know what else I would do. I constantly worry about losing my job and fear having to live through another nightmare as I am tired. Whenever, I make a mistake I feel a sense of shame that others are judging me a dumb and that I some how do not deserve to be in this position. While I know I am successful to some degree, How come I view myself so negatively and most always feel less than others? I would like some feed back from others.
    Thank you

  • Dao

    I really understand you.

    I think people who handle daily that much shame feelings or being worthless feelings are “heroic” in some ways! Those are not easy feelings to manage and feel frequently.

    So be proud of yourself for having make your way through life, with this challenge in addition (having to manage shame feelings or negative views of the self).

    Some people seems to be lucky because they don’t have to handle as much those feelings daily (everybody feels shame, but not with the same intensity or frequency).

    So, be really proud of your strength for handling all those feelings et for having try and strive toward a better life, always.

    I don’t know you, but I am impress with your strength!

    P.S. Sorry for my english, it’s not my first language! All the best to you!

  • lv2terp

    Love your descriptive writing style and wonderful message!!! Thank you for sharing this important insight! 🙂

  • Blomster45

    I needed this. Thank you. I am a 60 year old male. I lost everything i worked for for 27 years to bankruptcy in 2014 after the economy tanked.. This was made even worse by the fact that my partner of 8 1/2 years walked out 6 months earlier. I was totally embarrassed. Enough so that I had to move from the city I called home for 35 years. Still trying to get back on my feet. Good days and bad but have not given up. This is inspirational and I feel blessed by your perspective.
    Like the person (BK) who commented previously, I have always struggled with feeling not good enough and comparing myself to other people. Then, when I look back on some of the things I accomplished and was a part of, I blow myself away.
    I have to say that I am proud of myself, although it can be a struggle some days. I am still my own person and manage to look towards better days ahead.
    In starting over, I made a promise to myself that I would rather starve than be employed at something I hated, especially at my age.
    So, I am now on my third attempt at employment, having left a miserable position that actually paid more & feel that I have found something that I actually like doing.

  • Michelle Price

    BK, Thank you for sharing your story. You sound like an incredibly strong person. Dao is totally right. Be impressed with all your strength in meeting all these various challenges. Shame is indeed an intense burden to bear. I wish we all had a simple answer for you. Being the writer of this article, shame is obviously something I have been exploring. That being said, I think shame really is parasitic in nature. It needs a strong host to feed off of. I hope that in the midst of shame rearing its ugly head that you are able to see your own strength, your own beauty. I truly believe that reveling in your own unique self and journey is the most radical act of resistance against shame. Thank you again for your brave, expressive post.

  • Michelle Price

    Wow. I love what you wrote, “Then, when I look back on some of the things I accomplished and was part of, I blow myself away.” I too am blown away by your resilience. As a young person, it is humbling and inspiring to hear that people have to start over at all different points in there life. I wish you so many blessings as you search for work that will serve you on a deeper level.

  • Esmeralda99

    Yes! Thank you for this beautifully written article and the stories that it inspired in response. I needed to hear this exactly at this time. I am in my 50s and starting over, except that I was supposed to be doing that 2 years ago! I left a successful career to travel and try other things in a foreign country. Soon, my long-term relationship ended. I had no job and difficulty with the language. I doubted myself and my self-esteem was in the gutter. I was alone and very vulnerable. Some pretty boy took advantage and made me feel special, and I put my life on hold to make it work with this man.
    Just days ago, I found out that he has been having sex and/or various emotional affairs with other women during our entire relationship and before. (He has played on their vulnerabilities, too.) The shame that I feel is tremendous. I am a smart woman! How did this happen? Again?
    Maybe I was scared to rebuild my own identity. This identity crisis, uncertainty in a foreign language and country and my lack of confidence caused me to revert to old destructive patterns that I thought I had conquered many years ago in my 20s. Maybe you never conquer your difficulties but repeat them until you get them right.
    I am working to diffuse the negativity that I feel (including shame) by not adding any more negativity to the situation. It’s very soon, so I am not sure how I can do that. My thoughts can get very negative. But to paraphrase Eckhart Tolle, if I didn’t have this problem, I would have another problem. Life is not without problems. You didn’t do anything wrong because you have problems. Everybody has them! This has been helpful when I feel shame.
    As for me, the only way that I can live is fearlessly and by following my heart (probably in other things than men for a while). Yes, I should have seen this coming. But if I can use this horrible problem and learn from it – I can become happier because of it. And the sooner that I start my story, the better. This guy is not worth another moment of my time!

  • cplmrs

    This truly was an inspirational story. Yours is too. I am a 33 year old female who has tried everything to find work for many years. I have a degree in graphic design and worked as a full-time graphic designer until the fall of the economy. I switched gears and worked as a customer service representative, but hated everything about my job and decided to go back to school. While I was in school I also joined a job club where I established a connection with a fellow job seeker. I proposed a project to maybe put up a small business together that would get both of us out of unemployment. While we were working together a lot, I also developed feelings for my partner because we both understood each other’s situation. Things turned around for the worst when I ended up taking most of the project myself and when my supposed partner found out that I developed feelings for him, he laughed in my face. I decided to end everything. I terminated the project and cut my connections with my partner. The downside is I used up some cash for meetings at small restaurants thinking this project would take off. The upside is that it ended and I didn’t waste any more money than if it did take off.

    I haven’t given up though. I’m still finishing up my classes, volunteering, applying to jobs and not hearing anything from the places I have been applying to. I do feel lost but after reading this, I feel a little more hopeful.

  • AL

    “Whatever mistake you think you made, whatever wrong turn you might have taken, if it was prompted by the desire to expand your capacity to live fully or love and be loved, then you have absolutely nothing to be ashamed of. You need not repent for a thing. So quit condemning your heart. It is likely that it has suffered enough.”


    I went through something quite similar. I traveled to another country to meet my lover after being separated for almost a year (we had dated for 5 months before I moved). My traditional family was completely against it and her, to make a very long story short. They made my life crazy with constant disapproval and disappointment (I live with them). Plus, threatening to break contact while being depressed.

    Yet I packed my bags and left to be with the love of my life, not knowing what lay ahead. We spent two days and we couldn’t connect physically or emotionally even though we went through the distance better than many people I know. She broke up with me in less than three days.

    I’m left hurt, disappointed, dejected, angry, depressed before the break up and after (obviously!), ego and self esteem at an all time now.

    But, I have no regrets. I wanted to live my life to the fullest and all this is part of it. Rather go through the roller coaster than a log ride! As you said, given an opportunity, I’d do it all over again. Hopefully armed better the next time!

    Thank you for sharing your thoughts, Michelle! I really needed this!

    PS: Some inspiration from a very unlikely source:

  • Shanker

    Hi Michelle,
    I envy your choice of words and metaphors! As a writer myself, I enjoyed it a lot however.

    That apart, you’ve touched a crucial issue that most of us go through in life. Yes as you say, we all feel scared and ashamed during that time. Your points are a true guidance to all of us. And, we all should strive to be like your aunt, a real healer who might be the most important person in your life then.


  • Zen

    Thank you for the great article Michelle. Timing of your article was perfect as I’m going though extremely challenging time right now. Just came out of 9.5 years of marriage. I came to America as a foreign student. I met my former husband when I was so fresh of the boat. After years of giving my time and energy for his career goals and fulfillment I demanded that I want my own identity. I had a dream when I came to America, and it has gotten lost somewhere in between life’s unexpected things and the marriage disasters. As soon as my former husband realized I’m serious about my intentions he took off, leaving me with nothing. We managed to finally divorce. I didn’t demand any spousal support knowing him as a freelancing artist. I ended up with no place to go, can’t afford to rent any apartment, no money, and no family here. All the years I spent with him his family was mine, well I thought it was until we divorced. I was extremely polite and nice with all of his family members, because I come from the culture where we respect our spouse’s family no matter what. I was shocked how people can turn the other way so quick! Well, after couple of nights in my car, and 4 months of couch surfing, doing odd jobs and getting sexually harassed, and living off of food samples (thanks to Trader Joes and Farmers Markets) and showering at the beaches (thanks to sunny SoCal) I’m finally gaining my strength back. My neighbors took me in. I’m staying with them now. Number of jobs I apply every day is ridiculous but so far no luck. I’m a creative person. I like writing, but it’s hard to write anything when your mind is filled with basic survival and safety. My former husband said if I’m struggling then that was the choice I made when I decided to divorce him, and that he doesn’t owe me anything. Well, he is right, he doesn’t. Since our divorce he moved on and moved out of the country, and I wish him all the best, really and truly, from the bottom of my heart. I’m 38 years old, and every day I struggle with being nice to myself. I put all my energy and efforts so I try not to beat myself up harshly. For me it is a survival right now. Some days are good and some days is hard to get myself out of bed and I just want to scream because of all the voices in my head, so loud and not backing off no matter how I try. And of course people telling me “we told you, you should have left him long ago” or “well you knew what you are up for when you divorced” or your own shame which is harsher than anything else . Honestly, I’m not promoting anything or anybody here but books have been my solace and sanctuary. Brene Brown’s “Rising Strong” and Elizabeth Gilbert’s books, and empowering quotes and articles like yours are my doctors right now. They are helping me tremendously, as I can’t afford a therapy. My family back in my country don’t know I have divorced my husband, and they have never actually met him either. He never went to my country to meet my family. I’m trying to bring myself to a better place and gain some strength before I tell my family because I need to be strong for the outcome after they receive the news. I come from a conservative family. And of course after all these years in America I can’t go back to my country. I love it here. I just want to say regardless of anything I’m grateful. I got my car fixed and applying for Uber driving. I would like to acknowledge all the kind people that I have in my life, and meeting along the way as I go through this tough time. I’m so depended on the kindness of strangers right now, and this world is full of kind people. It seems so impossible now, but I know I will survive, I have to.

  • Michael Job

    Holy shit, this is one of the most amazing things I have ever read. I have lived a similar story. I let lust and love throw me onto the wildest emotional roller ever built. It threw me into the air and I crashed harder than I ever thought possible. I wouldn’t change the experience if you paid me, though.

  • Jacqueline

    Sometimes you just have to follow your heart. The ones who say ” I told you so”, live with their heads. A life lived with no passion is a poor life.

  • psu2454

    Thank you for posting this article that I needed so very badly. I recently put my all into a relationship very quickly, and while I did not follow him across the country, I still had friends and relatives telling me that I really should have known it wouldn’t end well. Doesn’t really help when you are already in a low place! I am also around your age and have been telling myself over and over again that I shouldn’t be this naive at this point in life, that I should know better by now. Anyway, this article was everything I needed so thank you for writing it.

  • Danielle McCafferty

    Oh my goodness the whole time I was reading your article I was shaking my head yes. I have always been a “fly by the seat of my pants-Head first-Leap don’t look-Heart on my sleeve “girl. I now am suffering the consequences of some of my past adventures. Guilt is a sugar coating to some of the pain & regret I feel. I am trying to forgive myself but find it quite difficult at times. Thanks for the reminder to quit condemning myself. 🙂