The Emotional Smorgasbord of Major Life Milestones
A birth, a proposal, a wedding, a move—all major milestones come with a mix of (often loud) emotions. It’s time to be real about all the complex feelings that accompany big life events.
Hey everyone, welcome to The Unlock—where we get straight to the heart of business leadership. I’m Matt Hunter, your executive coach, and resident wordsmith coming to you from Boulder, CO.
A bit about me: I’m an exited founder with 15 years of hard-earned stripes in building and leading companies, including co-founding Turnstyle (acquired by Yelp) and serving as President & CEO of Founders Pledge, which has rallied startup founders to pledge over $10B to charity. Alongside my business ventures, I've competed as a high-level athlete in college basketball, tournament golf, and ultra-endurance events. As a coach, I bring a deep interest in psychology and communication to elevate growth and later-stage founders and CEOs, steering them toward becoming standout leaders and fostering winning cultures.
If you’ve missed my previous posts, I’d recommend catching up with Reflections From a Recovering Maximizer, Financial Freedom Isn’t What You Think It Is, and Don’t Be Afraid of Tension. Ready to jump in? Let's go!
Pregnancy. Birth. Weddings. Moves. Career milestones. Graduations.
Major life milestones are no joke. They’re exciting, they’re memorable, they’re beautiful, and they’re also… super intense and emotionally complex. We’re told that these benchmark moments are meant to be the “happiest” of our lives—so no wonder we’re confused when these big events are accompanied by a whole lot of challenging feelings alongside excitement and joy.
My wife and I have been together for over five years, and I’ve felt the full spectrum of emotions every step of the way. To be clear, my wife rocks. I absolutely adore her. I feel like I won the lottery with whom I get to spend my life. And yet, at all the pivotal moments—the proposal, the wedding, the positive pregnancy test, and the (very recent!) birth of our first child—I have felt a wide range of conflicting emotions.
In these moments, we’re expected to be “up and to the right” with our emotions, especially as men. It’s gotta be all smiles. How could you feel anything other than overwhelming excitement and joy at the prospect of never dating anyone else ever again? How could you not be 100% stoked at the expectation of providing for several humans until they become adults? In the movies, we see depictions of people becoming overwhelmed with joy and meaning in these moments. As a result, we get the message that feeling anything less-than-stellar in these moments means that something is wrong. For many of us, that leads to suppressing valid emotions that deserve to be seen and heard during these times of change.
To be clear, I have found that there is always a part of me—you might call it my true self or my spiritual self—who is actually excited to move forward with these commitments. This part of me knows that moving forward is the best move, even if there’s some fear and hesitation. Overall, I feel great about the direction my life is moving. I feel great about being married to my wife and starting a family with her. And! There are other parts that are like bucking broncos. At these transition points, I’ve often felt like a cowboy holding on for dear life as I get tossed and thrown into deep experiences of sadness, loss, anger, grief, fear, and terror. Parts of me that value my free time and independence. Parts that are afraid of stepping up to the responsibility. Parts that simply fear the unknown.
I want to advocate for making all of these feelings OK (as you may know, this is kinda my thing). When we do this, we can let them pass through smoothly and return to a loving, integrated stance in our lives.
At this point in my life, I know to expect these big moments to feel like I’m in a rodeo and the gate is opening and I’m riding that bucking horse, doing my best to stay mounted. There’s going to be a lot of movement! I know that I’ve made these big commitments through careful deliberation and intention, and I ultimately feel excited. Then, when the gate opens and I walk through the portal into the mystery of the future, I’m expecting anything to happen. I know that it’s unlikely to be a smooth ride, even if it’s the “right” thing. So I’m prepared, like a cowboy with my hand close to my gun in a duel, ready for whatever might transpire. Or maybe it’s more like being a surfer in a tsunami. I’m likely to be overwhelmed, but I’ll try my damn best to ride the wave when it comes.
In August, I found out that my wife was pregnant. I’d just returned from a beastly, multi-day mountain biking trip with friends, and I was absolutely exhausted when I got home and received the news. Jane took a pregnancy test right when I arrived and it came back with a faint second line—meaning, she was pregnant! Wow. We did it. Getting to the point in our relationship where we both felt a level of fluency and trust in each other that we were comfortable taking the next step of becoming parents was something we had been working towards for almost five years. This was a huge milestone that we’ve worked hard to get to.
Immediately there were movie scenes flashing in my mind about the moment when the couple gets ‘the news’. A voice blared in my mind: “Get your ass off the couch and get excited.” And yet, all I wanted to do that Sunday afternoon was sit by the fire and read my book. I knew this was a significant moment for us, so I did what I could to put my exhaustion aside, connect with my wife, and share my excitement for the journey.
My feelings of exhaustion were followed by a messy blend of emotions. Immediately I started to experience these strange intrusive negative thoughts about my wife. Judging her. Thinking poorly of her. They were really scary if I took them at face value. The next couple of mornings, I woke up feeling depressed. Two days after confirming my wife is pregnant for the first time (a true miracle, a huge milestone for us), I’m feeling depressed and indifferent to life. Seriously? What’s the deal?
My wife rocks. I built the courage to share with her that I was having a hard time. She let me lay in her lap by the fire and asked me to share what I was feeling. I went through all the things I was experiencing. Sadness that my off-ramps are now gone. Sadness that I will no longer be the cool bachelor guy in NYC, I’ll be a dad in Boulder. There was fear that I wouldn’t be an interesting person anymore. I would have to sacrifice a lot.
And then for the hard part: I shared about the negative intrusive feelings I was having about her. I’ve come to learn that intrusive thoughts usually occur when I have some deep-seated challenging emotions that I haven’t processed yet. They are simply a signal that I have to deal with a more challenging emotion, and they actually don’t have anything to do with her. She and I gave that part of me some space, asked it what it was trying to do, and made it OK. And sure enough, I learned that it was trying to protect my heart. Taking the next step with her would add a whole other layer of depth to my heart. This part of me wanted to make sure it was safe for me to go there.
After those few days of accepting and processing my emotions, the challenging stuff subsided and made way for excitement and joy, which I experienced for most of the last nine months. By accepting my ‘unacceptable’ emotions, I was able to enjoy the lovely feelings that we would all expect to feel in those situations.
Here’s the thing: In these big moments, no one talks about how a whole smorgasbord of feelings is the norm. I want y’all to have a clear takeaway here, and the takeaway is this. Challenging emotions should be expected in these big moments. We are human beings, and we need to embrace that this is the nature of being human.
The real problem is when we make our natural human experience not OK; when we bottle up the big challenging emotions and feel like we can’t talk to anyone about it. That’s when things get dicey. So please, lean on a friend, lean on your partner, lean on the people you love. Get real about your experience. The magic of being human is that if we can acknowledge our emotions, especially in the presence of a supportive partner, they start to loosen their grip and move on.
This gives us the internal space we need to truly embrace and enjoy these big moments—in all their messy and imperfect beauty.
On the Radar
⚫ What I’m Reading: I’ve been reading a lot of spiritual books at night lately and really enjoying the experience. I just finished Awareness and Rediscovering Life by Anthony De Mello. Anthony is an Indian Jesuit and is very provocative, giving you his no-holds-bar approach to spirituality. Very thought-provoking reads.
⚫ Epic Highlight: Max Holloway KO’s Justin Gaethje right at the end of an epic match. Warning, this is a UFC highlight of two men fighting each other.
⚫ Spirituality Tour: I recently completed the Hoffman Process. I wanted to do it before becoming a dad. Wow. It was awesome. Very worthwhile and super challenging. Definitely check it out if you’re interested.
⚫ Ask Matt: Respond to this email with questions or topics that you want me to write about and I’ll consider putting them in future posts.