Setting aside everything I think I know.
How things always have a way of working out, practices to help with mental health, and following dreams of passion and purpose.
Buried amongst all those Black Friday emails, here we are. Officially moved over to Substack. There’s a feeling of optimism in the air again - for those of you that track the astro, we made it out of Scorpio season. Holy smokes what a ride.
And now we land, with a clear vision of where we’re going, and what we’re doing - how exactly we get there, is all part of the adventure game, and I’m not in the results business.
Today, in ‘Money making and business building in a flailing economy’, I share the experience of things always having a way of working out, even if there seems no way through at the time. Some call it magic, but there’s a strategy to the whole thing. A process of surrender, of letting go, and setting aside everything I think I know about how a situation is going to unfold.
We’ve been working on our titles, can you tell? And in ‘Corporate Counter Culture’, a series of Q&A with business leaders talking about profound hippie shit, dear friend Matt O’Leary shares his tools of navigating challenging times, and how his experience has set him on a path of purpose in a new professional endeavour. People following their dreams with passion and purpose - this is the good stuff right here!
Happy Thanksgiving y’all.
—Holly Gottlieb (Founder, Whole Collective)
Corporate Counter Culture: Matt O’Leary
Matt is a former Chief People Officer at Zepto, previously holding leadership roles at Spotify and Honey. He is currently exploring his own venture at the intersection of high-resolution audio + mental health (sound+wellness).
Holly: I have been talking to a lot of senior folks who are in the middle of career transitions - I’m curious about your approach to becoming focused and staying optimistic in this process.
Matt: Building good habits and healthy practices that work for me has been incredibly valuable, as it’s easy to let the self-imposed career and economic pressure become a bit overwhelming. I’ve found that actively working towards improving my sleep, eating consistently better, and regular exercise have helped build a stronger foundation to stay focused and inspired. Also, staying connected to friends (in person and online), practising gratitude and self-kindness, finding beauty in the natural world, learning and committing to quiet time have also helped tremendously. However, we are all wired differently, and what works for each of us will vary, but I know from experience (and practice) that there is value in trying to find our own version of this.
Holly: How have you arrived at the practices that you use today?
Matt: It’s been a combination of necessity and a desire to find and be the best version of myself, but I know these things don’t come naturally or easily to many people - they certainly didn’t for me. I’ve had to work hard to make progress, and it’s rarely a straight line to improvement. If I'm not making progress, I stop to ask myself - what can I do differently to shift this thinking or this trajectory? Recently, however, I’ve allowed my passions and aspirations to balance my pragmatic realities, which is driving a transition to embrace music as a form of therapy. I’ve always had a profoundly intimate connection to music, and it’s been my pathway to mindfulness and a version of meditation that works for me. I’d like to help make this accessible to more people.
Holly: I love that you touched upon the music, your profound attachment to it, and its impact on your mental health. I believe we get set on these paths of finding more profound meaning and fulfilment for a reason. One of the concepts Whole Collective is centred on is how you define and build what you know you're here on this planet to do, but in a way where you can still be financially self-supporting and pay the bills whilst you build your creative dream.
It sounds like you’re exploring a business in the music space that expands upon this concept of mental health and well-being. Does that feel like something born out of some kind of darkness…. out of a need to find a more profound calling within you?
Matt: Yes, very much so. It’s still early, but I am working on a music therapy concept born from three compelling forces.
Firstly, the challenges in finding the balance of sustainable emotional and mental fitness have played a significant role in allowing music to become a therapeutic partner in my quest for sustainable happiness and well-being. Secondly, a growing body of excellent research proves how powerful music can be for healing and health. Finally, music as a form of therapy is such a primal force of inspiration for me that it’s become clear it’s one of the ways I can meaningfully contribute to society. I feel very fortunate that this is so vividly clear to me.
I think we are reaching a new level of awareness of the therapeutic benefits of music, and it’s a tremendously exciting time. I’ve been inspired by prominent people like James Blake, who openly and eloquently talks about his mental health and relationship to music and is producing new compositions specifically for the benefit of our well-being.
Holly: Any closing thoughts or remarks about the state of the world? A message of hope for today?
Matt: I understand the sense of hopelessness that can sometimes feel overwhelming, regardless of circumstances or people's perception of you. There is excellent help available in various forms, and while there is value in developing a level of resilience and self-dependence, you don’t have to do everything on your own. Equally, it's very easy to judge someone from afar without knowing what's happening in their mind and lives, and asking questions with dignity and humility while leading with empathy can only be a positive thing for the world. Finding the courage to be maturely vulnerable and being receptive to someone else's vulnerability can be a powerful force for good.
We are rapidly evolving as a civilisation and society, perhaps too quickly in many ways from a technological perspective. Yet, while horrendous tragedies happen in real-time around us, there is equally a lot of hope, optimism and faith about what we can accomplish when we come together. Incredible humans are doing amazing things in their local communities every day, and we shouldn’t lose sight of that in the fog of terror or tragedy.
Business Building & Money Making in a Flailing Economy
Setting aside everything I think I know, by Holly Gottlieb
After 7 years in the US, I now get the holiday cycle pretty well. This week is like any other in the UK. It’s that full speed drive til the end of the year, and then the week before Christmas everything shuts down, lethargy and gluttony set it, and you can expect emails returned in early January at best. In the US it seems Christmas isn’t as big, Thanksgiving is major, but it all rolls into this weird in-between period - less than 6 weeks til the end of the year (there I said it), is enough time to make some major progress in business, and yet it holds that undercurrent of frustrating holiday delay.
In the face of what appears to be interesting economic uncertainty, added to a holiday week where most are focused on more festive matters, I’m driving to get new business in, and it’s very easy to get daunted by this time and think, ‘what’s the point, no-one's going to reply’. And yet, a favourite saying from my friend Kate, is ‘to put aside everything I think I know…’, a paraphrase of the 12 step set-aside prayer. It’s a helpful one to pull out today.
As I unpack my relationship with money more and more, I see how there’s a pattern of anticipating defeat before I’ve even begun. It leads to procrastination, and a general sense of helplessness. But it’s really bullsh*t. I’m calling myself out. Because in that process of unpacking, I have also created a ‘positive evidence board’ - a big sheet of ALL the times things have worked out in my favour, when I had NO clue how things were going to be ok:
the visa that came in
that client that arrived out of nowhere
the house that magically appeared
the people that showed up when they weren’t there before
the lover, the friends, the exact amount of money….
There’s a lot more on there. But in the center of this big sheet of paper, in big red capital letters, I have written, P R O O F.
Because it is proof. A reminder to myself. That EVERYTHING has worked out so far. Never in the way I expected or wanted it to, but somehow, it was never the catastrophe or defeat I was expecting. That’s not to say there wasn’t extreme difficulty, pain and fear, but in riding waves through those nights of hell, I seem to somehow be standing on my feet right now. In fact, every single one of those moments somehow worked out better than I ever expected.
It kinda blows my mind….
And I have to remind myself of that right now. As I’m on a mission to pick up work and find aligned clients, I could very easily find all the reasons to not even try. It’s the holidays… no one will reply… companies aren’t hiring… everyone is looking to next year already… blah blah blah.
But what if I took those words of advice, and set aside everything I think know, and continue putting one foot in front of the other, and see what wants to meet ME? Maybe, just maybe, things might be working out for me, even now?
And maybe I don’t need to send emails this week. Maybe I don’t need to kick myself for not being able to take the ‘forward progress’ I want. Because maybe my idea of progress isn’t actually the one that’s going to move the dial. If I look at all the ways those things on my PROOF map worked out before, was it ever as a result of me hustling and grinding and trying to make things happen a certain way? Nope. Never. Not a single one.
Ok. So a reframe. I’m not going to make things happen in the way I want. What can I do instead? What other actions can I take? I’m not advocating for doing nothing. Sometimes that is needed - I find when I’m confused about the next direction to take, I’m really just being asked to sit, get quiet, and pause.
This doesn’t feel like that kind of time. The clarity is piercing. Of what I’m doing, of what I’m building. It’s like I’ve been collecting different puzzle pieces over the last 5 years, and I’m only just starting to see how they all fit together…. It’s a map! Where I get to pull in all the things I LOVE doing, all the things I’m GOOD at doing, and the things I get PAID well for doing.
This motivation and drive is a FIRE inside me right now. There’s no doubt it’s going to get used, just not in the way I want it to.
So I made a business plan for next year. In ten years of recruitment, that’s something I’ve never done, well not for me at least. At my old company we had to project our numbers for the coming quarters / year, but it was never something that felt genuine to me. And now here I am in November, with this piercing clarity, and engine-revving fire, pulling together everything I have ever learnt into a clear plan of how I get this ship sailing. Of how I build the life I have been dreaming of for so long. Building it on rock, not sand. THIS feels genuine. THIS feels achievable.
When I return to the PROOF page, I might not have had any idea of how those things were going to work out, but I was holding a vision for them. For some it was a conscious vision, for others it felt like once they arrived it was an obvious feeling of ‘oh yes, THIS is what I wanted.’
So I write this business plan, this dream of the future of what I want, I am creating the vision. I am saying very clearly in black and white, ‘THIS IS WHAT I WANT’. But the HOW isn’t really my business. I keep showing up to the next action as it arrives, in this case writing this email, pushing send, refining the business plan, reaching out to the folks I feel inspired to…
In putting aside everything I think I know about how it’s all going to work out, I’m actually allowing the space for it to do so. Never in the way I expect. But always in a way that is supportive to my vision. The PROOF literally tells me so in big red ink.
What a game of adventure this all is. One foot in front of the other. It feels like show time.
Holly has 10+ years working with high-growth companies (primarily in tech, media & CPG) to scale their teams (at the CEO level through to entry level hires). Her primary focus is now working with mission-driven / purpose-led companies and founders who are building for the betterment of people & planet. Ideally in a fractional recruiting capacity. LinkedIn HERE.
