Five Proudest Moments

“I don’t fully understand my life until I write it.”

–Robert Frost

Think back through your life and think about what you are most proud of. The items on your list could be things you accomplished “out in the world” or things that happened internally. Knowing who you are and where you’ve come from, what have you done in your life that you are most proud of?

The definition of what makes you proud is yours, not anyone else’s. The things you choose to put on your list don’t necessarily have to coincide with what other people would choose as your greatest accomplishments, but rather the ones you personally feel proudest of. It could be a moment you showed great courage for instance, rather than a time you won a public award.

If you were to die tomorrow, list the five things you are proudest of in your life.

If you can’t think of five, stretch until you do. If you come up with more than five, winnow them down to five. Honing the list is part of the process.

Once you have your list, write two-three sentences describing each one…sentences that fully captures what you did, said, or accomplished, as well as the obstacles you overcame to do so. Take your time until you’re sure each sentence reflects exactly what you want to say.

Here’s an example from a time I did this exercise a number of years ago:

My Proudest Moments

  1. I set clear boundaries with my mother in order to establish my separate identity. Then after decades of struggle and eight years of estrangement, I reconciled with her, growing to accept her as a complex, imperfect, generous human being whom I could honor, love and respect.

  1. Despite the baggage I carried from childhood and the obvious challenges of being a lesbian parent, I found a partner, carried two babies in my womb, pushed them out of my vagina, and then continued to let them crack my heart open again and again and again.

  1. At 28, I faced the incest with my grandfather, stood up to my family, committed to the rigors of the healing process, and ultimately used my anguish, pain and courage to inspire others to heal.

  1. I have learned (and am continuing to learn) to move myself off center stage, to surrender control and to say, “I’m sorry” and “I was wrong.” Every day, every moment I take a step in this direction is a great victory for me and for the people I love.

  1. Despite being constantly sucked into the world of doing and the incessant demands of my ego, I have claimed my right to a spiritual life and a spiritual perspective, and am slowly, doggedly, building an inner life for myself.


  1. Cathy Hall Stengel says

    1. In spite of growing up without loving parents, in fact with abusive parents, I carried, loved, delivered, and raised three children along with my husband. The love that was born into these children surpassed and continues to surpass anything I ever knew myself.
    2. At 45 years of age I faced the sexual abuse of my childhood, entered therapy and began to tackle the healing road. Surviving this process was not a given to me and yet I have persevered as I become a more whole and realize that I am a sacred person of worth.
    3. I am learning that I cannot earn love and care, but rather I am worthy of love and care. I am enough for today, more for tomorrow, but enough for today.
    4. At 52 years I separated from my father, establishing absolute boundaries between us. As long as the cruelty continues, there will be no contact. As challenging as this estrangement is, it has allowed healing space where I can stand back from the toxicity and cruelty and not accept it as my own.
    5. At 54 years I am learning that my feelings are valid. Enough said.

    • Debbie says

      Cathy – this is a great list and accomplishments of which to be very proud! Your line “I am learning that I cannot earn love and care, but rather I am worthy of love and care. I am enough for today” – really touched. This is a learning I continue to work on integrating into my “reality”. Thanks for the inspiration!

    • Ilana says

      Cathy- This is beautiful and you helped me to recognize some things I should be proud of. For instance, being far better parents to our children than our parents were to us. I really loved your last line, though. “I am learning that my feelings are valid. Enough said.” It just underlined an already powerful piece.

    • Terry Gibson says

      Carol, I love your list and those are no small accomplishments. Hard work behind it all. I also liked the sentence Debbie quoted. Thanks for writing this and sharing it with us.

  2. Carol Harper Phillips says

    The five things in my life that I am most proud of are:
    1. Care giving when my mom, grandmother and dad had cancer. This extra help allowed them to stay in their homes for longer than if I hadn’t been there to help out. I learned a lot about human nature, our mess of a healthcare system, and many family “secrets” which were quite an eye opener.
    2. Volunteer work with animals, gardening, music groups, Grey Bears and travel. This was, and still is very healing for me, especially working with horses,cats and music. It is said that music was used by the creator to sing the world into existence.
    3. Finishing my degree at UCSC in my 40’s. This was accomplished with little help financially or emotionally, especially from family. The one exception was from my grandmother who finished her degree in her 50’s after raising 3 sons as a single mom.
    4. Raising and helping to raise 3 kids to adulthood, and 3 grandkids. Two of which are adopted, one from overseas. All were high maintenance special needs type kids. We are still in recovery from this!
    5.My home, which is my heart and soul. It took years to find the land and oversee all that was involved in the construction of the house. It is here that I will spend my final days.
    All in all it has been a good life.

    • Debbie says

      Carol – Raising children, caring for the infirm, creating “home” are all fundamental parts of our lives and certainly something of pride! Thanks for sharing your list.

  3. beverly Boyd says

    There are many accomplishments I am proud of. I chose to focus on five of those times when I was able to be completely in the moment, having a clear understanding and acting truthfully even when it felt I might lose something by doing it. Instead I gained something far more valuable: my self-esteem.

    1. I refused to play the fake stripper party game in order to save the one bachelor’s date from embarrassment. All of the rest of the wives followed us out of the room and left our hostess with the pile of pretty underwear she planned to use for props.
    The bachelor and three other husbands, including mine learned about it and thanked me.

    I protected my younger siblings by putting myself between them and my rampaging mother.
    It was enough to make her “come to her senses.”

    After years of a difficult relationship I told my sister that, even if we never agreed on things, I loved her and I wanted to have a loving relationship with her as my sister.
    Not only did our relationship change, she told me before she died recently that knowing I loved her had started her own healing and healing of other relationships.

    I said “No” to the real estate agent who wanted me to ask the black family in the neighborhood to keep their children in their own yard until our house was sold.
    We were in escrow within a week!

    I set boundaries with my mother and claimed my adult status. After a few minutes of telling her what was bothering me, I told her it didn’t matter she was too old to change!(55years old). That got her! She said she was not too old to change and she’d think about it.
    She started going to a therapist and made a lot of changes that began healing our family.

    • Debbie says

      Beverly – I found your list inspirational! And validating that when we stand in our own truth, with kindness, our world can change. And in your case, it also changed the world of others in a positive way. Thank you for sharing these accomplishments with the group.

    • Ilana says

      Beverly- I love how full your list was of times you stood up for yourself and said, “No.” Just reading it was empowering. Thank you for sharing it with us.

    • Terry Gibson says

      Beverly, I love your list. Those moments when we stand up for ourselves feel so great, don’t they? I must admit that a little smile came to my face when I read about what you said to your Mom; that would work with me if somebody said those words. Thanks so much.

  4. Camilla Sørensen says

    My Proudest moments
    1. When I finally found out about the incest and so entered the healingprocess I became a proud suvivor working hard to becoming a proud thriver.
    2. It took me many years to find the courage to say no to my mother, and to set clear boundries, though I am still learning, I do say no to her today which makes me proud of my hard work with boundries.
    3. At seventeen I went into a plane for the first time, flew to the other side of the world all alone, thus after a year of studying mostly with myself, I came out as a lesbian.
    4. When the words come they come faster than I can write. I wrote my first story when I was nine years old. I write whats in my heart even in two different languages which makes me proud of my creativity.
    5. I listen to people and I never judge a person for their past. I change peoples lives by listening and seeing their true heart and spirit, so with a little interest I guide them in the right direction, which makes me proud of my ability to see another human being openly.

    • Debbie says

      Camilla -it is almost like your list took us chronologically through your life with each accomplishment building on the one before. This is a terrific list of special gifts. I am glad you shared it.

  5. Fran Stekoll says

    1. Defying my parents and listening to the words of “Too Young” when marrying Wayne March 14th 1954 at the age of 19.
    Even though the marriage only lasted 46 years, my proudest moments gave
    me two daughters.
    2. Defying Death by beating the odds on November 5, 1958 after birthing Sheri. Her birth defects were challenging; but I didn’t want to have an only child.
    3. Adopting my son Alan, through the Grey Market, in San Francisco September 10, 1961, supporting him in finding his birth father .
    4. Caring for my Father and Mother and Aunt until their deaths.
    Brought me closer to understanding how necessary Long Term Care Insurance was. I don’t ever want my children to have the burden of my care.
    5. Graduating from College at the age of 44. Working part time, raising three
    children, catching my husband cheating with my best friend. Surviving through it all gave me the strength and courage to achieve whatever comes.

    • Debbie says

      Fran – thanks your sharing your list. You have much to be proud of! My favorite line that you wrote – “Surviving through it all gave me the strength and courage to achieve whatever comes” – That learning is absolutely something to shout out to the world.

  6. Fran Stekoll says

    1. Watching 9 out of 10 of my Grandchildrens births. The only one I missed
    was Perle September 24, 1987 as she was born in Paris, France, yet she is
    my closest Grand Daughter.
    2. Meeting Matt May 9, 1997 at the Ideal Fish Restaurant answering an ad
    for my Mother and realizing when he said “forget your Mother I’ll take you”
    I would have the best 15 years of my life.
    3. Accepting the presence of God. Coming from a Jewish background and being born again to the words of Sandi Patti singing “We shall behold Him” and Josh Grobin singing “You raise me up”
    4. Being fired from a job I loved. Gave me the opportunity to start my own
    business which I successfully ran for 28 years.
    5. Realizing it’s ok to live alone. It’s now time for just me. I feel if I died tomorrow I have lived a full and rewarding life. Being a Widow isn’t that bad.

    • Debbie says

      Fran – your list is wonderful and full on special moments. Thanks for posting it with the group.

  7. Debbie says

    1. Making the commitment to living an “authentic” life –
    There have been moments over the past thirty years when I made a conscious choice to turn away from fear or expectations of others and listen to my intuition about who I am and what nurtures my soul. The goal was, and still is, for the outward persona and the internal personality to overlay identically into a single, cohesive view of “me”.

    2. Caring for my father when he was dying –
    This experience literally changed my life, career path and sense of service to others. It introduced me in an intimate way to one of the greatest mysteries we face; our own death. I am proud of making the decision to support his wish to die at home without condition or regard for “consequences”. I have been rewarded many times over for this opportunity to love deeply, learn and serve.

    3. Maintaining meaningful, long term relationships with the most important people in my life –
    I am not wired for the facebook concept of “friends”; numbers don’t count so much to me – rather the quality of relationship does. There are a handful of special people in my life for whom I care deeply – some over decades. This includes a recent, successful transition of my long-term life partner into a life-long friend without rancor or bitterness. I worked hard to preserve the friendship even those our roles were changing and I am proud that together we have accomplished that.

    4. Having a career that supports service to others –
    I think it is a gift to have a career that feeds you personally, as well as, literally. I found my way to that type of career through having the commitment to living an authentic life, courage to “start over” by returning to school in my mid-thirties walking away from a successful business career and the desire to never stop learning and growing.

    5. Lifelong commitment to learning and personal growth –
    I am deeply committed to continued development on a personal, relationship, professional and spiritual level. I continue to be a “work in progress” and I am proud of how that mindset has enriched my life with new knowledge and experiences.
    Laura – I approached this exercise with great trepidation – thinking the number five was way too many things to be proud of!! But as I finished working on this post early Saturday morning – I want to thank you. I am leaving this writing with a greater sense of my own value and “justification” for taking up space in this universe. It was really inspirational and I am grateful you forced the topic and magical number “5”!

    • Ilana says

      Debbie- Thank you for sharing these amazing achievements. I love how you talked about what you have accomplished and then said, “I’m not done yet.” in #5. Bravo!

      • Debbie says

        I hope I never think I am “done”! There is so much yet to do , to learn, people to care about and experiences to discover! Two days before my father died he regained his ability to speak (which he had lost for the prior five weeks). We were able to talk briefly and he indicated he knew he was dying. So I was able to ask him if he was scared and he gave me this wonderful gift. He said “I’m kinda scared but I’m kinda excited, too.” I hope I can carry this same sense of adventure with me to the end of my life, as he did.

    • Terry Gibson says

      Debbie, I feel quite close to your list. It is very similar to mine. I love everything you have, especially the part about being authentic and a work-in-progress. Thanks so much.

  8. Ilana says

    The Five Things I am Most Proud of

    I am proud of my cooking. I’ve been afraid of food all my life. I used to look at a meal as a terrifying challenge. “How am I going to get the food from the plate to my stomach?” The easiest thing was to move it around on the plate to make it look like I’d eaten. I was anorexic, undiagnosed because I wasn’t convinced that eating would make me fat; just terrified of the food. Like so many other problems I had, no one noticed so no one helped me. Then, one day, as an adult, I figured it out. My fear of food was anorexia and a direct result of the incest I had suffered as a child. “Well! I’m not going to let that bastard take this away from me, too.” The first thing I did was to give myself permission to fail, something I had never allowed before. One after another I tried new recipes and shocked myself by creating something edible. Me! That terrified little girl who believed she was so useless and inept. I am cooking and entertaining! People like my cooking!

    I am proud of my voice. Such a silly, vain thing, really. I never admit it other people but I like the sound of my voice. I sing whenever I can; with my children, when I’m alone and every week when I pray with my little minyan. I grab every opportunity I can to chant the Torah portion or the beautiful Haftarah blessings. When I sing in front of other people I never admit to how delicious the melody is in my mouth. I deflect the compliments with a quick “Thank you” never letting them in. It is with shame that I admit to my innermost self that I think I have a pretty voice. Secretly, I know that my voice turns prayer into chocolate on my tongue. It turns songs into pastries and musicals into buffets filled with every kind of delight I could dream of. Shhh. Don’t tell anyone. If they knew that I like my own voice they’d know that I am ill mannered and full of myself.

    I am proud of my newfound ability to let someone else get the last word. The first time was at minyan. Arthur was running the service. The rabbi was guesting and he was in some kind of a mood. He felt the need to publicly correct everything that Arthur did. I’d never liked him much but I still felt sorry for him. I’d been corrected in front of everyone, myself, and I knew how humiliating it was. As I went up to sing the beautiful Haftarah blessings my joy was a bit tarnished by the discomfort the situation had created. After services, Arthur pulled me aside. “You’ve got the second troupe wrong. I’m sure no one noticed but the rabbis and me but the second half of the first word is supposed to be flat, not uplifted.” Was he serious? Most people merely read this blessing and some even mispronounced the words without being corrected. The second half of the first word…? Then it hit me. He was hurting from the public humiliation he had suffered. He needed to be the one correcting. ‘Alright.’ I decided. ‘I can give him that.’ I smiled brightly. “Thank you. I’ll study it some more and get it right next time.” He smiled with satisfaction and I went home telling myself I ‘took one for the team’ so to speak.

    I am proud of my ability to support others even as I struggle myself. Week after week I sit in my support group and look at the faces of my sister-survivors. Sometimes I laugh but more often I want to cry. Most days I am struggling just to breathe but I am safe. They are there for me and I am there for them. Last week I looked at my beautiful friend, “You’re not gross!” I insisted. “Gross things were done to you but you are not gross!” Her face turned scarlet and tears spilled down her cheeks. “Thank you, Ilana.” She whispered and the look on her face ripped my heart from my chest. We are all in this together and I can give as well as receive.

    I am proud of my newfound ability to withstand this painful process of healing. “I’m not going to take the bull by the horns. I am going to fly in his face.” I have explored every opportunity for healing that has been presented to me. This last one was the hardest, by far; a ‘trauma sensitive yoga class’. It shocked me, how intensely I was triggered by simply breathing and getting in touch with my body. I spoke with the facilitator after class. “Yes, this is to be expected. That is why the teacher keeps suggesting grounding techniques. ‘Watch your fingers move, feel your feet on the matt.’ The point is to learn these techniques here, in a safe place, so you can use them in the outside world.” I thought about it. “I’ll be back next week.” I promised. “You don’t have to. Take a break if you need it.” I shook my head. “I wasn’t making the commitment to you. I was making it to myself.” She smiled. “I’ll see you next week then.”

    These are the five things I am most proud of. I can’t share them with too many people but I can share them you. Thank you for asking

      • Ilana says

        Thank you, Laura. I hope I will sing for you one day. Maybe by then, if you say I have a pretty voice, I’ll be able to let the complement in. Now that would be an accomplishment!

    • Debbie says

      Ilana – Cooking, entertaining, singing (in public!), being supportive with your sister survivors (and us), understanding when someone’s need may be greater than yours and making commitments to yourself regarding continued healing – WOW! – look at all you have already accomplished! You have much to be proud of! Thanks for sharing your growth, talents and support with us. P.S. I just love this line “Secretly, I know that my voice turns prayer into chocolate on my tongue.” What a strong image of enjoyment!! I have been thinking about this since my first read – returning now for my second!

    • Terry Gibson says

      Ilana, what a fine list you have. I really love your line about not letting the bastard rob you of food’s vital nutrition, as well as your joy of cooking. Supporting friends while in the process of healing; I find myself doing the same and it really rocks to be able to give someone another perspective on things. Between us, I like my singing voice too and I don’t think it’s vain. When we spend so much time putting ourselves down, it sure is about time we give ourselves a bunch of pats on the back. Lots of love and encouragement to you.
      To you and all mothers here, Happy Mother’s Day!

  9. Terry Gibson says

    Five Things That Make Me Proud

    Despite life obstacles that make Mt. Everest look like a speed bump, I found my way and continue to use a checks-and-balances approach to life. Even with that concentration, which I slip up on sometimes, I seem to have fashioned a career, of sorts for myself, thanks to my laptop. The fact that it involves words and writing is absolute heaven to me.

    I ran away when I was in Grade 10 so only I motivated myself to stay in school, which provided a needed structure for me. My desire to learn was never sated; I was the first in my family to finish high school and go on to university. I’ll get my degree even if, by time my graduation happens, I suddenly ‘wake up’ and wonder why I’m at a strange party with people wearing dark robes and flat square hats.

    Three reasons make me proud that I am not a mother right now. One, I believed it was a given that I, as an abused child, would be an abuser; I was terrified of my rage and visiting it upon an innocent. Two, I grew up in such poverty, I couldn’t do the same to a child–especially when I know the pain of having a fine mind and unlimited potential, but, due to a lack of resources, having to let much of it fade away, unexplored. Three, I would’ve had to have two children at least; I have no extended family and it would’ve been wrong to have a baby because I wanted one, while knowing that when I die, she or he would be all alone in the world.

    With all the shaming, humiliation, and stigmatizing I experienced in my first 20 years, taking a chance on AnyOne was highly unlikely. However, thanks to Joan, my first social worker, I started that long journey by degrees, and somehow kept going. I am an observer of life and recently my doctor said that having the ability to watch, is what ultimately saved my life. It is also because of the compassion and love that somehow sprouted within me, as if through a dense thick wall, with each new and outrageous abuse I endured.

    After I figured out how, I took on the criminal justice system, on behalf of my siblings and myself; I had my brother and sister’s okay, so we all told our own part of the experience. This activity helped us all as we were grieving the loss of our oldest brother, 35, who had just died of alcohol poisoning; we were all eventually awarded criminal compensation money for therapy or whatever. In a continued commitment to my brother, Steve, I also flew back east many times after he was diagnosed HIV+. I’m proud that I travelled 3,000 miles to be with him for life-or-death brain surgeries, his paralysis, loss of speech, a premature stint in palliative care, etc., while the rest of the family was within five miles and didn’t show to comfort him.

    • says

      Terry, I’m so glad you finally posted before the week was out. I am, as always, moved by your courage, strength and fortitude. Your brother is so lucky to have you.

    • Debbie says

      Terry – this is an amazing list of inspiring actions. There is much to be proud of in what you have accomplished to date. I get the sense you aren’t done yet, either! Thanks for sharing with such honesty.

    • Terry Gibson says

      Thanks Debbie and Laura. Your words always mean a lot to me. Yeah. After I finished that poem, I had trouble focusing my thoughts on anything. I wrote and re-wrote these five things a few times, only to scrap them again. By the way, you’re right, Debbie, I’m definitely not done yet. (I even forgot to say that I’m lucky in love and proud I ever got to be intimate emotionally with friends, let alone physically with lovers.) That’ll start my new list. 😉

    • Ilana says

      Yay! Terry posted!! Your strength is inspiring as is your ability to recognize it and give yourself credit. As Laura said, your brother is lucky to have you and so is the rest of the world. We, each of us, touch so many more lives than we know. I am glad that you touched mine.

      • Terry Gibson says

        Thanks Ilana. That enthusiasm felt like a hug to me. Been needing them these days. I’m struggling a lot right now but hanging on.

  10. Karla says

    1. I am present in my own life. I am wholeheartedly engaged—intellectually, emotionally, socially. At times I think I am connected to everything in the universe, big and small. I am my own person.
    2. I have spoken for those who are voiceless under the most vulnerable of life circumstances. I have transformed the fear I felt as a child into ways to understand battered women who defend their lives against their abusive partners. Working with women accused of murder has created the kind of meaning for my life that I didn’t know I needed.
    3. I have learned to love without control, if imperfectly. It is a struggle for me to let go of what I want for my child and get out of the way so he can find whatever his passion is. It is difficult to give my partner the joyful freedom to pursue what he needs even when it irritates me beyond what I ever expected.
    4. I have said, “I’m done.” To my father, the last time he attempted to bully me. To relationships that didn’t move me. To friends who didn’t get me.
    5. I have said, “I’m here.” To my father, after a debilitating stroke, whose vulnerability I expected would evoke revenge, but instead brought a rush of love that seemed linked to the core of who I am. To my first true love affair, as she waffled daily in whether she wanted to be with me. To a friend, who was willing to give me the space to get myself.

    • says

      Karla, Welcome to the Roadmap blog and thanks for sharing your powerful life accomplishments. I especially loved the juxtaposition of #4 and #5. I’ve been there with my own parents. P.S. If you’d like to get more response from the other writers on the blog, that will probably happen when you respond to the current post. Keep coming back!

    • Beverly Boyd says

      I was so moved by your share. I wonder if your willingness to be honest in #4 made it possible for not only you but also your father to be present for $5? It seems to work that way. It did for me.

  11. Karla says

    Thank you, Laura.

    Thank you, Beverly. I think that you’re exactly right abut the connection between these things. That is partly why I wrote them in that parallel way. At some level, I think we can only be here (there?) for people when we are also willing to walk away from them. That’s true choice, I guess.

  12. Bobbie Anne says

    This list is one of most difficult things I have done, but I’m writing it because I need to. It is time for me to do this. Now.

    My Five Proudest Moments

    1. Even though I was abused,builled and hurt, I don’t do the same to others. I try to diffuse situations that could turn abusive or badly. I am amazed by how often this works for me. This comes with my faith in God.

    2. I am glad I became a teacher and I taught and still teach, with the student’s goals in mind. I’m more of a guide on the side and I listen, really listen, and then we go on from there.

    3. I am glad I am a writer and a poet. Yes, I did get published and won awards for my poetry, but the best thing is knowing that what I write made someone else feel happy, or even if they cried when they read it because it touched them or struck a chord or made them think about something they had to do. That is priceless.

    4. I am a cancer survivor. I am glad I have thrived instead of dying. I have decided to help others as much as I can, and I go to a cancer survivor’s support group. I’m so glad I’m still here writing this list. I had another birthday. Happy Birthday to me, Laura and all cancer survivors!

    5. When a health care worker sexually assulted me, I was glad I was able to get his license suspended so he can no longer work in this state. I did this without the help of the police. In fact when I did report it, I was humilated, and the police detective told me he couldn’t help staring at my cleavage. I stood up to him with courage.

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