That Moment When You Question Everything: Is This My Midlife Crisis?

by Michael Keeler

[Disclaimer: This is not a typical post for a business blog (maybe it should be?). So if you’re not ready for some raw, unfiltered emotion, this may not be the post for you.]


Right now, as I’m typing this, I am having a moment when I am questioning everything. And by everything, I mean all of it–my life. Not in a super dark life isn’t worth living kinda way, but in a what the hell am I doing with my life sorta way.

You ever have one of these moments?

Mine seem to come about every 18-24 months. It’s not a precise cycle, but it’s a cycle. And this one seems a little more intense then the others have been.

Is this my midlife crisis?

If someone was to look at my life from afar at this very moment, humbly, they’d have reasons to be impressed. I have an incredible life partner who is one of the greatest humans you’ll ever meet. I own two very successful businesses that make me comfortable financially. My work is often very fulfilling, working with amazing coworkers and clients who make me feel like my contributions are valuable.

I live in a beautiful apartment in a lovely neighborhood with a great view of the NYC skyline. I have incredible friends who are caring and support and fun. I have good health and many of the people around me are well and thriving. Plus, I have a laundry list of other privileges that frankly put me in a class of people who are never supposed to complain about their lives.

All of that is true. But that fact is, I’ve been incredibly unsatisfied for the past few months. And I can’t help feel ashamed that I’m unhappy.

With everything going right in my life, what the f*ck am I doing being unhappy?


Gratitude sometimes feels like a tool I want to use but it’s locked away in a treasure chest that I’ll only find by decoding some ancient Indiana Jones-style scavenger hunt.

The movie that continues to play on repeat in my mind is one of continuous questioning and judgment and aimlessness, asking myself…

What the heck am I doing in NYC? This place is noisy and dirty and mostly unpleasant. If I never had to ride the damn subway again I’d be so happy.

What am I doing running a fitness company? I don’t even like working out. What an impostor.

What right do I have to coach other business leaders and owners? Is this what I really want to do for the rest of my life? Am I even any good at it?

What is the end game of all this work? Am I really going to make an impact on anyone or anything?

Then my problem-solving brain turns to what if questions followed by even more judgment…

Well, what if we just picked up and moved somewhere else? Ugh, who wants to make all new friends? That sounds exhausting.

What if I went back to school for something totally different? Maybe go to pastry school or become a psychologist. OMG, that also sounds exhausting. And expensive! I just paid off school debt, do I really want more?

What if I just really work on a business plan that excites me? Am I just a little burnt out? I feel like I’ve done this already. What good is more planning gonna do?


The cycle continues on an endless loop of self-doubt, which leads to shame and judgment, which leads to more feelings or aimlessness and self-doubt.

Someone get me off this insane merry-go-round from hell. Ahhhhh, I’m gonna barf!

As a coach, I know that there are seasons in life and this will not last forever. But in the moment it’s hard (often impossible) to simply rationalize my way out of feeling restless. Plus, I’m not someone who will easily just let this thing play out, it will take care of itself. Nope. Not my style.

I also know intellectually that it’s a great quality to be able to question everything in my life. Striving for things to be better and stretching myself to achieve greater and greater things is one of my best characteristics. And that’s not at all useful information when I’m sitting squarely in the muck of self-doubt and uncertainty.

So then, what do I do?

Honestly, in this moment I’m not sure how I’m going to dig my way out of this.

In part, I’m writing this as a journal to help me process my thoughts and feelings — honestly not even sure if I’m going to share it publicly or not. And another part of me wanted to write it because I wanted other people to know that you’re not alone if you’ve experienced something similar.


We all go through times when everything looks great on the surface, but there is a tumultuous undercurrent that is forcefully trying to pull us under. That’s where I’m at right now and let me tell you, the current is strong.

In moments like this I ask myself,
what would I tell someone else who came to me in this situation? After all, I help people overcome personal and professional challenges for a living.

I’d say first, take time to be with your feelings. Sit with them and maybe do a little journaling to see what comes up. (Cool. I’m doing that now. Check!)

My second piece of advice would probably be that in my experience getting out of your head and into conversation with other people can be useful. I’d also say that taking action (doing something, anything) will teach you more than merely thinking about it.

Okay, so taking my own advice, what are some ways I can get out of my own head, into conversations with others and start taking action?

Let’s brainstorm. I could…

  1. Schedule some coffee dates with three of my best friends to talk about it.
  2. Talk to a coach or therapist.
  3. Find a personal retreat to go on that focuses on self-exploration.
  4. Plan a work retreat to explore a vision of my future work.
  5. Host a mid-life crisis dinner party. (Haha. This is just a brainstorm. All ideas are welcome!)
  6. Find a therapy or counseling group.
  7. Sign up to learn something new that is outside of my comfort zone.
  8. Hire a career counselor to help me analyze my passions and skill sets.
  9. Take a poll of my closest friends and colleagues to see what they think I’m best at.
  10. Make a bucket list of things I want to experience or accomplish in my life.

Those feel like some good options. It feels pretty good and productive to have made that list. ?

Now what? How do I pick which action (or actions) to take?

Well, shit. I don’t know. What would I tell someone else to do?

I’d probably ask, Which of these possible action steps evokes an emotional reaction for you? Which ones lights you up or gives you butterflies?

I like #1 (coffee dates with friends) because it would feel great to talk about this with people I trust and respect. It makes me feel warm and cozy.

I like #4 (work retreat to explore a future work vision) because it really pressed a nerve for me that my future work life seems unclear.

And I like #5 (mid-life crisis dinner party) because it made me giggle and seems absurd.

Okay, now I’m armed with three action steps that really resonate with me. I’m an overachiever, so I want to commit to doing them all.

Is that too much? Are they S.M.A.R.T. goals?

I feel the need to take some drastic action, so I’m comfortable taking on all three goals. And they feel pretty SMART to me. Each one feels Specific, Measurable, Attainable, Relevant and Time-Bound. Oops, not really that last one. What’s a reasonable time-frame for me to take this action?

I’ll commit myself to take action on all three by the end of this month and have all three completed by the end of next month.

Let’s check in. How am I feeling?

For starters, I’m tired of typing. #truth


Beyond that, I still feel like I’m in the muck, but honestly, my inner monologue of negativity has gotten much quieter. I feel just about 1% more optimistic now that I have some clear action steps to take.

I think I’ll share this with my husband tonight just so I have an accountability buddy to ask me about my progress. Plus, I just like sharing with him anyway. He’s the best.

Should I post this publicly? Hmm, not sure.

Will it read like some self-indulgent, over-sharing, pseudo-psychological-self-exorcism? Will co-workers or clients be put off or hurt by my admission of not feeling fulfilled in my life?

Or might it be helpful for people with similar challenges to see that they’re not alone? Could it be useful for people to see how I tried to apply my coaching skills to myself? Could it be useful to lead with vulnerability in the hopes that it encourages others to do the same?

Well, if you’re reading this I guess you know what I chose to do.

Thanks for reading. Cyber Hugs!



  1. Tamara Christie

    This is such a great post, Michael. I think we all have those moments! I really enjoyed the process you used here to come up with some action steps. Thank you for sharing, cyber hugs back atcha! xo

  2. Oscar

    Thanks for this post Michael! We all go through moments like this and it’s a good reminder that even those we look up to have a crisis every now and then. Keep sharing and helping!

  3. YA

    Read – and appreciated. Honest and relatable, and the recognition that this comes and goes should assuage any sense of oversharing or regret. We get it.

  4. Juliane Godfrey

    Dear Michael,

    I resonate SO VERY MUCH WITH THIS POST. You are NOT alone at all as I feel like I’ve been on the exact same journey for the past 4 months. I recently finished my first Broadway show feeling more miserable, restless, and terrified of my uncertain future than ever before in my life. I’ve taken a ton of small steps including courses in meditation, career counseling, therapy, talking to every friend and family member I know about what I’m feeling, and researching other careers and job opportunities non-stop as well as debating grad school. As a former Ninja and high-achiever myself, I so identify with your feelings of guilt and frustration when life seems to be pretty great on the surface, and yet you seem to have completely your personal life compass. I’d love to write you a similar article about my journey and where I’m currently at, and if you would like a digital accountability partner, I’m all ears. I think the company that you and Mark Fisher have built is truly remarkable and I am so glad that you had the courage to put these feelings out into the world. Rock on and know that I’m right there with you!

    <3, Juliane

  5. Tom Keegan

    Right there with you. I’ve mentored many, and have seen their success and cheered them from the sidelines, but have been afraid to truly pursue what I think I could excel at and be happy both. I’m my own worst enemy when it comes to making personal choices, especially related to my “career”.
    Instead, I find happiness in smaller ways. I find outlets to be creative, and to free myself, accept myself, love myself. While I probably should be more concerned about my long term planning, I find joy in the here and now. And most often, that’s enough.
    Yes, you are the zig to Mark Fisher’s zag; the yin to his yang; the vinegar to his oil. You’re both fine separately, but when you’re blended together, everything is as it should be.
    Will there come a time when you two need to go on separate journeys? Probably. Is that coming sooner than either of you expect? I certainly don’t know. But if some of your fears are whether or not to try something new, I usually say go ahead and try it.
    A friend once said she never regretted anything she did; she only regretted the things she never did.
    Trust yourself. Even if you don’t know the answers. Put yourself out there, and the answers will come.
    Thanks for sharing.

  6. Tim Goldman

    Thank you for posting this. I’ve been at a career cross road that has been causing me stress. I want to leave my current job but I am not sure what the next best step is and I am afraid to take the next step because I am not sure what the right step is for me.

    Perhaps identifying some actions I need to take to get me there will help me beyond looking for answers in job postings on Glassdoor or Indeed!

  7. Shanti Nagel

    I love this and YOU. I want to be on the coffee list! I have thoughts ?

  8. Michael Vinereanu

    Thank you for sharing this post! Please keep us updated on how your goals are coming along!

  9. Brian Crowley

    I loved this post, Michael! It’s comforting to know that others feel this way no matter their level of success. I love the list you made. It was invigorating to digest the idea that “taking action (doing something, anything) will teach you more than merely thinking about it”.

  10. Stella Kaufman

    I really love this “raw” post. Also, I am available for the mid-life crisis dinner party. Love you.

  11. Michael Keeler

    THANK YOU to everyone for your outpouring of support and affirmation. I’m so glad I decided to share this post because it seems to have resonated with so many of you. I truly appreciate all of your outreach and friendly advice. I promise to post a follow-up article about the next chapter of my journey (and photos from my midlife crisis dinner party, haha!). <3

  12. Geoffrey

    Aloha! In the past 5 months I’ve wrestled with quite a few self doubt loops coupled with a sprinkling of existential angst. Our ability to do self audits & ask hard questions is a blessing and a curse because we may not be able to come up with the answers to our own questions.

    Not to be dark, but I am often steered by the question “What would people remember me for/as if I got hit by a bus today”. I personally think you’re making an immeasurable improvement in many peoples lives, and that you are creating the change you wish to see in the world by teaching humans to be better humans. It just so happens that the humans you teach are the teachers of other humans, so your impact expands in a big big way.

    So many of the details we tend to worry about are arbitrary, and what really matters is that we live a life with the intention of virtue and goodness (at least that’s what I tell myself haha) . If that’s our standard, you’re on top of it!

    Love ya Keeler!

  13. Anthony

    I’ve had this blog post earmarked for reading for over a month now, just waiting for the right time to dive into it because I am going through the exact same cycle in my life right now. Your words resonated with me and my partner as we took turns reading it aloud to each other.

    What’s next? I have no idea, but this is some of the encouragement and questioning needed right now.

    Thanks for leaning into it and being brave.

    • Michael Keeler

      Thanks, T&A! I’m so glad it resonated with you both. Cyber hugs!

  14. Farid

    I don’t know, years after we met, the thought of you popped into my mind and I decided to look you up. Upon finding you on FB, I get inclined to Doha little deeper …I didn’t have to dig very deep to discover this post which happens to be very relevant in my life right now. I’ve begun doing some work in order to get me out of this slump and this article was just what I needed to read. Thank you for posting it.

    • Michael Keeler

      Thanks so much for reading it, Farid. I’m so glad this resonated with you and you’re working to get out of your slump. I’m here for you if you need any help or support. Hive fives! Michael

  15. Kate

    I honestly have those moments where you question about everything as you explained about twice a week. Only for like a few minutes because my brain starts hurting being so confused so I then distract myself. It use to happen once every 2 months but cause we don’t have much to do at home during the lockdown, it’s been having more frequently.

    • Michael Keeler

      Thanks for sharing, Kate. So glad to know I’m not alone. I also want to say that it’s important for us all to have some healthy coping mechanisms for handling these feelings when they emerge. Whether you cope by distracting yourself with work, or use medication, or make artwork, (or whatever!) it’s okay to purposefully walk away from these feelings until you’re ready to address them more directly. I hope you find what works for you! 🙂


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