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

[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!

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