Disappointment: So You’re Not Where You Thought You’d Be
There is a particular kind of ache in reaching an age you once imagined differently. This essay makes room for disappointment without shame, invites grief for what has changed or been lost, and offers a gentler question: is the life you pictured still your real longing, or is it time to choose again?
As a therapist, I’m privileged to be invited into the hearts and minds of many amazing, bright, brave people.
And in my many years of doing this work, one thing I seem to hear over and over again is a sentiment that goes something like, “I’m just not where I thought I would be by age [fill in the blank].”
This sentiment seems to be, at least in my personal and professional experience, indiscriminate across ages, gender, professional sector, education level, or tax bracket.
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It seems that most of us , myself included , have the thought from time to time, “This just isn’t where I thought I would be by now.”
If you’ve had this thought, too, what I share in today’s post may resonate.
The big reckoning.
Many of us seem to have ideas about where and who we would be by certain ages , particularly those watershed ages like 25, 30, 35, and 40.
Prior imagined lives where, perhaps, we were partnered to the person of our dreams, surrounded by loving community, thriving at work, maybe even achieving a level of fame or notoriety, and certainly financially abundant.
We all have our own version of what we thought life was going to look like for us.
A picture in our minds that, when we do arrive at that age and experience a disconnect (be it big or small) from that painted picture, can cause us to feel sad, frustrated, or even resentful of life and ourselves for not taking the path that we believe would have gotten us there.
I’ve come to think of these thoughts and the time we dwell on them almost like a reckoning.
It’s a time where, for many of us, we take stock and often perceive ourselves and our lives lacking.
So what’s to be done?
I don’t think there’s much to “do” when we arrive at this place, but rather we can allow , we allow ourselves to feel whatever comes up for us around this.
Still not married and struggling to even find a relatively functional person on Tinder?
Feel your sorrow and anger about that.
Deep in student loan debt and nowhere near where the experts say you “should” be in terms of saving for retirement because the cost of living is so high in your city?
You’re allowed to feel your fear and frustration about that.
Watching your college friends achieve massive professional success by launching venture-backed companies, being promoted to partner, even getting their 2nd or 3rd book published?
You’re allowed to feel jealous about that.
No matter what, we must allow ourselves to feel the spectrum of emotions we have about not being where we thought we would be at such and such age.
The more we tell ourselves, “It’s wrong to feel this way”, or “It’s petty of me to feel this way,” we layer on more judgment and shame on top of already-painful feeling states.
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So please try not to do that. Allow your feelings to be whatever they are.
And if we need to grieve where we are, we do that, too.
It may seem “extreme” to use the word grieve in talking about life disappointments but I think that as the years progress and we move away from the years of invincible, wide-open options (such a common emotional state for teenagers and college-aged somethings), and as we plod forward into adulthood, we accumulate losses that need to be grieved.
The essay uses grief to name the emotional work of facing losses in relationships, bodies, work, financial opportunity, dreams, and imagined futures.
In plain terms: You are allowed to mourn a life you thought you would have. Giving that loss a name is not self-pity.
Sometimes these losses are actual deaths of loved ones, losses in our bodies’ abilities, losses of romantic partners, lost jobs, lost financial opportunities, lost dreams and lost choices
And we weave these losses into our story, they add a kind of sober temperedness to us, a patina of realism and pragmatism in how we view the world that is so different from the invincibility of our teenage and college-aged years.
Listen to me: There is nothing wrong with needing to grieve the fact that you’re not where you thought you would be. You actually do get to grieve this.
And after the grieving, we can pay attention to the disconnect between our reality and our dreams, to our disappointments, and we can ask ourselves, “Is this what I imagine I should be/do or is it an actual longing? Do I truly deeply still want this?”
The essay distinguishes an actual heartfelt longing from an expectation about what you thought you should want by a certain age.
In plain terms: Your disappointment can be information. It may point toward something you still want, or show you that an old picture no longer fits.
If it turns out that your disappointment points to an actual, truly heartfelt longing, it’s a clue for you to perhaps course redirect.
For example, if you still want a healthy, functional marriage and lifelong partnership, that’s beautiful. And it may still be possible.
And so when the thoughts and attendant feelings arise that you don’t have this, it’s an opportunity for you to revisit how you can more and better invite that into your life.
If you are envious of your friend for launching a company and receiving series of funding, check in with yourself: is that truly what *you* want to do, or is it what you thought you should do based on your education or expectations from others?
If it’s not what you truly want to do, and instead if you want a quieter, more simple life in the country working remotely for someone else’s company, that’s FINE.
It’s so important if we’re struggling to reconcile where we are with where we thought we would be, to evaluate if that vision we had in our mind even fits anymore.
Times like these, when we despair over the disconnect between where we are versus where we thought we would be, can be such a great opportunity.
It can be an opportunity to feel our feelings, of course, but also to take stock and reevaluate what it is we truly want.
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And then, if possible, to move closer to that in some small way whether this is in external action or by doing the inner work necessary to achieve this.
Moving forward.
There is no big thesis, no silver bullet, no how-to, necessarily, to today’s post.
Instead, I hope you gather from what I wrote that feeling sad/frustrated/disheartened by where you find yourself in life versus where you thought you might be at a certain age is a very common and human experience.
There is nothing wrong with you for feeling this way.
It may be uncomfortable, yes, to have these thoughts and feel the feelings that come with the thoughts, but it really is important for you to allow yourself to feel your feelings about this , no matter what they are.
Of course, it can be an opportunity, too, for you to self-reflect and ask yourself whether that vision you had in mind by a certain age even fits you anymore.
If it does, if it’s truly a deeply held longing of yours and it is still possible in some degree, you can course redirect and do whatever necessary external and internal work you need to get there.
Rarely in life is it ever too late for some semblance of our dreams and desires to take place in some form or another.
And if you find out that that vision isn’t at all what you want any more, that’s very important information for you!
So remember, please don’t shame and blame yourself for having thoughts about regretting or mourning where you’re at a certain age. This is a perfectly normal experience.
I’ve included some links to some of my other posts below in case these may feel helpful to you as you sit with the thought and feelings that you are not quite where you want to be in life.
Please do leave me a message in the comments below and let me know if they feel helpful to you.
Here’s to healing relational trauma and creating thriving lives on solid foundations.
Warmly,
Annie
Q: Why do I feel disappointed about where I am in life?
A: The essay describes this as a common reckoning between a current reality and an earlier imagined life.
Q: Is it okay to feel jealous of friends’ success?
A: Yes. The essay gives permission to feel jealousy, sorrow, anger, fear, and frustration rather than layering shame on top.
Q: Why call disappointment grief?
A: Because adult life can include real losses of people, opportunities, abilities, dreams, and choices that deserve acknowledgement.
Q: How do I know whether to change direction?
A: Ask whether the disappointment points to a deeply held longing or to an expectation that no longer fits who you are.
Q: Is it ever too late?
A: The essay’s stance is that it is rarely too late for some form of a dream or desire, even when its shape changes.
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Annie Wright, LMFT
Licensed Marriage & Family Therapist · Relational Trauma Specialist · W.W. Norton Author
“Helping driven women finally feel as good as their résumé looks.”
Annie Wright is a licensed psychotherapist with 15,000+ clinical hours since 2013 and an EMDRIA Certified Therapist. She’s the founder and former CEO of Evergreen Counseling, a multimillion-dollar trauma-informed therapy center she successfully exited. She’s currently writing her first book, The Everything Years: Navigating the Pressure and Promise of Your Thirties, with W.W. Norton (2027). Her expert commentary has appeared in Psychology Today, Forbes, Business Insider, NBC News, and The Information.
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Annie Wright, LMFT
LMFT · Relational Trauma Specialist · W.W. Norton Author
Helping driven women finally feel as good as their résumé looks.
Annie Wright is an EMDR-certified licensed psychotherapist and relational trauma specialist with over 15,000 clinical hours, and she's been in practice since 2013. Trained in EMDR, psychodynamic, and somatic modalities, she is licensed in 14 U.S. jurisdictions and registered to provide telehealth in Florida (California, Colorado (telehealth only), Connecticut, the District of Columbia, Florida, Illinois, Maine, Maryland, New Hampshire, New Jersey, New York, Texas, Utah, Virginia, and Washington). Annie works with driven and ambitious women from relational trauma backgrounds, and everything she writes about is field-tested across thousands of clinical sessions. She is the founder and former CEO of Evergreen Counseling, a multimillion-dollar trauma-informed therapy center she built, scaled, and successfully exited, and is currently writing her first book, The Everything Years: Navigating the Pressure and Promise of Your Thirties, with W.W. Norton (2027). A regular contributor to Psychology Today, her expert commentary has appeared in USA Today, Forbes, Business Insider, Inc., NBC, and The Information.
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