People pass through our lives and change us, tilting our orbit with their own. Sometimes, if the common gravitational center is strong enough, they return, they stay. Sometimes they travel on. But they change us all the same.
Maria Popova
I write a lot about the importance of friendship and about prioritising the relationships that matter most to you.
Yet I lost a great friendship by choosing my family over a business opportunity three years ago.
Some days it feels like it just happened. Other days it feels like a lifetime.
The choice I made was avoidable - if I had listened to myself sooner and had more confidence in my long term path.
I’ve tried to apologise and reconnect a number of times - by text, by email - the kind of messages you write and rewrite five times before hitting send.
Trying to find the right words to make it better.
Nothing.
So why am I writing this now?
Because I haven't been able to let go of my regret at losing this person from my life.
The regret that I could have done things differently and that my life is a little worse off from not having this friendship.
I'm writing this in the hope I can let go of that weight and to remind myself to listen to my instincts.
And maybe, just maybe, I hope that she reads this somehow. And even if she doesn't reconnect, she knows how sorry I am for letting her down.
I first met Megan Dolce just over ten years ago.
Ryan, my investing partner, and I had recently made our seed-investment in Elvie, whose first product was a Kegel trainer for postpartum women.
We were brainstorming ways to help the company and, having already made inroads into the CrossFit community, Ryan suggested we meet Meg, who was an athlete at his gym and who worked at Lululemon, overseeing culture, marketing, and brand.
We arranged to meet Meg on the rooftop at Soho House in New York City's Meatpacking District.
Meg had a swagger and style that commanded attention. She had a unique way of making you feel seen and heard while at the same time sharing her strong and passionate opinions.
Ryan and I immediately warmed to her as we sipped our iced oat lattes, looking out over the New York skyline.
Meg took a keen interest in Elvie and, in particular, the founder Tania's story and mission.
After Meg and Tania spoke, Meg agreed to pitch her bosses on the idea of partnering with Elvie to distribute their products.
Whilst the pitch didn't work, we'd shared enough calls, ideas and laughs with Meg that by then we’d become friends.
Through her passion for health, wellness, and nutrition, and leveraging her platform at Lululemon, Meg always seemed to be at the cutting edge of health and wellness innovations - company launches, new gyms and workouts, nascent trends.
Ryan and I were focussing our investing on health and wellness so Meg became one of our go-to sources of feedback and insight.
In return, we always looked to introduce Meg to exciting founders and entrepreneurs who we thought could benefit from her unique insights and experience.
The opportunity for Meg and I to work in lockstep came shortly after my ill-fated decision to join Ample Hills.
It became apparent very quickly that the company needed a clearer, sharper voice and a strong organising energy around the myriad of partnerships and projects we were trying to execute on.
The founders of Ample Hills, Brian and Jackie, fell in love with Meg almost immediately. After a few weeks of consulting, Meg agreed to come on full time as our Director of Marketing, Brand, and People.
But in real terms it meant I had a partner to act as another adult in the room.
The list of projects we worked on during Meg's time are too many to mention, but the way she navigated the quagmire of Disney corporate to deliver a 3-month pop-up activation to celebrate Mickey’s 90th celebration (we can't call him a mouse or the event a birthday!) on a threadbare budget and with minimal other team members is a particular highlight in my memory.
During this time, Meg taught me so much about culture, communication, and strategy - she helped fill in the glaring gaps in my skillset that the role continued to expose.
Our time in the trenches forged a true friendship and collaborative partnership between us.
Despite the amazing impact Meg was having within the company, it was obvious that she ultimately needed to be building her own business - that she should be the boss.
Unfortunately, that realisation came to a head in the worst possible way.
As the challenges mounted for Ample Hills and we looked at all ways to manage costs, the founders decided Meg's role could go.
I objected but lost the fight.
Meg's frustration with the company and her deep-rooted desire to be her own boss meant she agreed to leave despite my protests. I knew the company and I were worse off for it.
What happened to Ample Hills? I've written about it in various ways.
But in the aftermath of the bankruptcy and the struggles, I had to rebuild my own confidence and decide on my next steps professionally.
Meg was a constant source of support and encouragement. At the same time, Meg had begun to build her own leadership and development company, RIPE.
She was the first to identify the potential I had as an executive coach and willingly included me in her progress with RIPE, her learnings, and the tools she was developing.
Her initial client base included professional athletes and the leaders of some of New York's hottest start-ups and the impact of her early work meant the business grew quickly.
Meg began to think about ways to expand the capacity beyond just herself and our discussions about me becoming more involved picked up.
Slowly but surely, I found myself in fairly regular calls with her, either learning the fundamentals of coaching or being a sounding board for projects she was developing.
A new opportunity arose to design and implement a leadership development course for a fast-growing e-commerce company in Vancouver. Meg suggested I work with her in designing the content and then travel with her to implement it.
Here's the thing: I wasn't mentally ready to commit to executive coaching at this stage. The idea of being a facilitator at a bigger leadership off-site made me feel very uncomfortable.
But eager to get back into things professionally and kick-start my coaching journey, I didn't push back hard enough. I let myself get swept up in Meg's excitement and creative energy and said yes when I should have said not yet.
A month before we were due to travel to Vancouver, my wife found out she had to travel internationally at the same time.
The idea of both of us leaving our three kids (10, 7, and 6 at the time) made me feel sick to my stomach.
I remember sitting in my home office, staring at my calendar.
My wife's trip: non-negotiable work commitment.
My trip: something I'd agreed to but dreaded.
And right there in the middle of that week were two events I'd marked months before - a singing performance for my 7-year-old and a class celebration for my 6-year old
The kind of events where your kid scans the audience looking for your face.
The kind of things that come and go so quickly.
I spent days trying to solve it.
Could my wife move her trip? No.
Could I go to Vancouver for fewer days? Not really - Meg was counting on me for the full programme.
There wasn't a solution.
When I finally got on Zoom to tell Meg I was cancelling, I could see her face change before I'd even finished the sentence.
She didn't lose it at me - from what I remember she didn't speak for a few seconds, then tried to reason with me. But I had made my mind up and despite feeling guilt and shame I also knew I was making the right decision.
Of course she was angry - she had every right to be.
I was leaving her in the lurch less than a month away from a huge project commitment that was hugely important to RIPE and the growth of her company.
That Zoom call in January 2023 was the last time we spoke.
I still see Meg's posts sometimes - Instagram throws them my way, and honestly, I'm glad it does.
Since letting her down, Meg has had a baby daughter, and I believe has another child on the way.
Her husband Eric, himself a fitness and wellness entrepreneur, has joined RIPE as CEO of her company.
And RIPE itself appears to have gone from strength to strength. I am always so impressed and amazed at the incredible content and insights that Meg and RIPE share.
I'm genuinely proud of what she's built, even if I'm no longer part of it.
As I get older, I realise more and more that when I think about mistakes I've made or regrets I have, it isn't the exact decision that led to the outcome that was the mistake.
It was the decisions leading up to the main decision - like the straw that broke the camel's back.
Because if I steal an expression from Dr. Becky, one that I remind myself of regularly: two things are true.
I regret deeply letting Meg down.
I regret deeply losing her as a friend.
But at the same time, given that same choice, I'd choose my kids every time.
And it's in this realisation that I've learned that being more present in the smaller decisions helps make the tougher, bigger decisions easier.
I should have said no to Vancouver from the start. I should have been honest about not being ready.
I should have had the courage to disappoint Meg early rather than catastrophically late.
I miss having Meg as a friend, as a mentor, and as a thinking partner.
I'm sorry I let you down, Meg. You deserved better from me.
