5 Huge Life Disappointments (& Recovery Strategies)

Are you disappointed by something in your life? I sure am. Here’s how to recover and feel better even if you’re dealing with each of these five biggest midlife disappointments. Buckle up my friend, because it’s gonna get a little stormy. And then it’ll blossom!

Usually I write blog posts in response to readers’ comments (such as moving on after a midlife breakup), but lately I’ve been struggling with disappointment. I’m 54 years old and it feels like life has been one disappointing thing after another. Especially lately; I can’t find a job, I’m not eligible for EI (Employment Insurance in Canada), and I’m still struggling with grief, guilt and regret for leaving my marriage.

Right now I feel powerless and helpless. I know it’s just a disappointing stage for a middle-aged woman who is still adjusting to a huge life shift. I know that this too will pass. I know I’ll get through it, and in a year I won’t even remember how disappointing life was.

How do you feel about your life? Even if you’re perfectly happy right now, it’s important to become aware of the most common midlife disappointments for women 50+. This list reveals the biggest challenges of growing older alone and prepares us for the future. Best of all, it allows us to start developing coping strategies.

If you’re struggling with one disappointment after another and you’re a middle-aged woman like me, you’ll find hope, comfort and companionship in this blog post. I hope you won’t be disappointed! 🙂 

Biggest Disappointments in Midlife (Plus Recovery Strategies
Blossoming in midlife despite disappointments

Right now I’m facing two of the most disappointing events of my life (numbers one and two in the list of midlife disappointments). My first was being childless (infertility prevented us from having kids), but at least that disappointment spared me from one of the other midlife hurdles (problems with adult children).

1. Marriage didn’t work out

A failed marriage—or midlife breakup of any kind—is the worst disappointment I’ve ever faced. Actually, calling a separation or divorce “disappointing” doesn’t even scratch the surface of the grief, regret and guilt of leaving my husband. I’m disappointed in both myself and my husband for not trying harder. We could’ve spent more time trying to save our marriage than just resigning ourselves to letting the relationship slowly wither on the vine.

After investing years into a relationship (I was married for 17 years), the end of a marriage brings a profound sense of loss and failure. I never expected to face a midlife disappointment like this—and definitely wasn’t prepared to lose friends in addition to my marriage. Ending a marriage in mid or later life also causes financial instability and retirement planning issues.

For me, a recovery strategy for this midlife disappointment is reading (and rereading) Conscious Uncoupling: 5 Steps to Living Happily Even After.

Going through a breakup or divorce is tough, but this book describes how to break up in a way that doesn’t leave you and your partner broken. Conscious Uncoupling helped me through the worst grief and guilt of leaving my husband. It also showed me that even though I was so disappointed (heartbroken!) that my marriage failed, at least I wasn’t alone. I could move forward into a happier, healthier midlife – even if I was growing older alone.

marriage failure is one of the biggest midlife disappointments for women

2. Job dissatisfaction and unreachable career dreams

I started my She Blossoms blogs about 20 years ago. They were my primary source of income, and I loved blogging. But over the past five years I was leaving my marriage, traveling in my camper van, and working at full-time temporary job contracts. As a result my blogs bring in no money at all. I’m out of work, and it’s one of the most disappointing parts of my middle-aged life. I’ve never felt as helpless or powerless. I’m working hard to find a job, and to work with the thoughts that are causing me to suffer.

Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett and Dave Evans is a tool for rebuilding (or restarting) your career and recovering from disappointment in midlife.

coping with career disappointment for midlife women 50 plus

If you’re a creative woman – or you need help thinking outside of the disappointing midlife rut you find yourself in – this book will help you design a life that matters. The exercises will help you rethink your career and life goals at a time, and plan the second half of your life.

A quick internet search tells me that job dissatisfaction is a common midlife disappointment for women 50+. Unachieved career goals and dreams, no opportunities for advancement or professional growth, or simply the realization that our work isn’t as fulfilling as when we were in our 20s or 30s are all disappointing. And as I’m finding out, changing careers as a 54 year old woman is not easy.

3. Friends drifting away or dying

Remember how easy it was to make friends when you were younger? My university days were my best friend-making seasons (except for when I was married. Making friends was much harder after I said “I do”). Now, however, I’ve found myself disappointingly friendless in middle-age. I can’t seem to find true friends who are kindred spirits. I live in a retirement community with lots of older people who are my friends, but it’s just not the same as when we were young and fresh.

It seems like my long-standing friendships have faded away or even been completely, deliberately ended. It’s hard, and very sad. Again, the word “disappointed” doesn’t even begin to address the pain and grief of losing friendships with people you knew when you were younger.  

I’m reading Supercommunicators: How to Unlock the Secret Language of Connection right now, and love the “no small talk” tips.

disappointing midlife friends for women over fifty

If one of your biggest disappointments in life is your lack of friends, maybe it’s time to learn how to connect better with people. Supercommunicators offers practical advice on nurturing and maintaining friendships in midlife and beyond.

4. Adult children are disappointments

I don’t have kids, so being disappointed in my grown children isn’t something I struggle with. I did, however, do a little research. I discovered that even if adult children are successful, healthy and happy they can still be disappointing to parents. For instance, a grown child might move a different city, province, state or even country. If they take their partner and kids with them, then you’re disappointed that you can’t see them on holidays or special occasions – or even for a walk to the park.

One of my older friends has a 37 year old daughter who is planning to move to Europe. My friend is disappointed of course, but also wants to be happy for her. His daughter is excited and happy, and making this midlife move is good for her professionally and personally.

If your adult children are involved in unhealthy, immoral or even criminal activities then they may be the biggest midlife disappointment you’ll ever face. I can’t imagine what it’d be like to remember the joy of being pregnant, the wonder of having a tiny baby to care for, and the challenge of raising a child. How disappointing is it when you’re facing typical middle-age issues and your adult child’s life is in turmoil?

Here’s a recovery tip to consider: read Doing Life with Your Adult Children: Keep Your Mouth Shut and the Welcome Mat Out by Jim Burns.

biggest midlife disappointment for women is adult children's choices

Parenting adult children can be tricky, and you’ll be disappointed if you think that it gets easier as they get older! Being a midlife or older parent is complicated because your heart and your head are as involved as ever, but your relationship is shifting – whether your child lives under your roof or rarely stays in contact.

5. Aging parents are getting sick or dying

As I mentioned, my mother struggles with mental illness (schizophrenia) and lives in a group home for seniors. She isn’t a midlife disappointment for me because I made peace with having a mentally ill mother when I was in my mid-20s. It was a very painful time—I remember well how hard it was to accept that I didn’t have a dad and my mom wasn’t emotionally available—but now I’m not dealing with aging parents. 

Most women 50+ are dealing with the harsh, sad reality of aging parents getting sick or dying. Even if you expect to care for your elderly mom and dad, it’s still a profound midlife disappointment. Witnessing your parent’s health decline—both body and mind—is painful and sad.

You may also be facing your own health and mortality issues. If you’re a childless woman growing older alone like I am, you know there will be nobody to take care of you in your old age.

Are you taking care of your elderly mom and dad? You may find it helpful and comforting to read 36-Hour Day: A Family Guide to Caring for People Who Have Alzheimer Disease, Other Dementias, and Memory Loss.

biggest midlife disappointment is caregiving elderly parents

Caring for an elderly parent or grandparent with dementia is worse than a disappointment in middle or later life. It can feel overwhelming, scary, and even unbearable. This book offers practical tips and compassionate advice that make the caregiving journey a bit more manageable.

Blossoming despite midlife disappointments

I know how difficult and disheartening it is to be disappointed by how life is turning out. It’s not easy to face the second half of life without the same energy and enthusiasm we had when we were in our teens, 20s and even our 30s.

On the upside, midlife brings experience, wisdom and even freedom to women 50+. Despite the challenges and disappointments I’ve faced, I also know I’ve learned a lot in my 54 years. I trust myself more, I’m less worried about what people think, and I believe that blossoming in midlife isn’t about perfection. It’s about authenticity, peace, and acceptance.

How are you coping with the biggest disappointments in your life? Your thoughts and feelings are welcome below. I know I missed a lot of disappointing midlife events – such as a broken engagement that makes you fear you’ll grow old alone.

Take good care of yourself.

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  1. My twin sister’s biggest disappointment right now is that we’re turning 40 in three months. Not me! I’m going to spend my 40th birthday racing exotic cars in Vegas, then flying to Mexico for a week, lying on the beach, golfing on perfect turf, going to see Mayan ruins, racing dune buggies in the sand, scuba diving, and planning my new business idea.

    Forty is not old….you’re as young as you feel. IF you wanna go get all responsible for your 40th birthday….go ahead…..or you can embrace the fact that you’ve only lived 1/3 of your adult life and have plenty more to go!

  2. Thank you for this website!! I feel much better knowing I am not alone in my sad feelings about how my life is turning out. 

    I am turning 45 in 2 weeks and my husband and I have barely been on speaking terms for 10 years. Unhappy at home but don’t know how to leave.

    And I hate my job, so that’s a huge disappointment. I don’t want to share what I do for a living because I’m supposed to be kind, upbeat and patient all the time. I hide the fact that I’m just a disappointed middle aged woman who is stuck in a rut in her life.

    Anyway, thanks again for your Midlife Blossoms blog. I found it by searching for disappointed in life, and am glad to be here.


    1. I’m glad you’re here, Jen – thank you for sharing a bit of your life with us! It’s been almost two weeks since you left your comment, which means you must be turning 45 soon.

      It really is a drag to be disappointed in your marriage and your job. Those are two of the most important parts of life – it’s where we spend almost all of our time.

      When you feel that the time is right, maybe you could start making small changes. Not risky ones, but little ones like rewriting your resume or looking on job websites for possibilities. Little steps are more powerful than you think 🙂

      Another little step is celebrating your birthday in a special, meaningful way. Here are a few ideas to get your creative juices flowing:

      40th Birthday Ideas for Women Who Want to Blossom

      All good things,

  3. I am 42 years old and me and my husband were trying to get pregnant and found out that I had blocked ovarian tubes. I had surgery to correct this and was told that the only way we could conceive was Invitro. We went through the Invitro and I still cant seem to get pregnant. This is definitely the biggest disappointment of my life and I feel majorly discouraged. I am adopted mom to 6 of my God children but I’ve always wanted my own child.

    I waited to try to conceive until I got married but now I’m in midlife and it seems that all of my friends are getting pregnant by mistake. My husband would like to continue trying but I don’t think that I can handle the depression that comes when we don’t conceive. I have only shared my true feelings about not being able to conceive with a few of my friends and family because people can be so insensitive. I am told to pray and not give up hope but I must admit that Im feeling pretty hopeless. I’m afraid to build up hope and be disappointed, again. I feel so guilty that I feel so hurt when people I know complain about getting pregnant or married couples complain that they are pregnant and didn’t want anymore kids. I know that God would not put more on me than I can bear but this is so very hard.

    Thank you for saying that some women with adult children are disappointed by their choices. Maybe this is wrong but it makes me feel better that not all mothers are so happy with the way they children turned out.

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