47: Your First Million Live

Podcast art for episode 47 of the Leaving Well podcast with Naomi Hattaway

Resources and articles mentioned in this episode:

Your First Million Live

Your First Million Book:  Bookshop or Amazon

To learn more about Leaving Well, visit https://www.naomihattaway.com/

To support the production of this podcast, peruse my Leaving Well Bookshop or buy me a coffee.    

This podcast is produced by Sarah Hartley.


Transcript:

If you can’t find a reference, then it’s your job to become one. -William “Classic” Thomas

Leaving Well is a new concept in the United States, as it relates to workplace transitions, as is the formal container for interim executive leadership, even though it’s an indisputable reality that People Leave. I have been using the concept of leaving well as it relates to moving from place to place for many years, and in 2018, started realizing how closely the concept correlated to the workplace. Besides the amazing work of Jerry Jones as it relates to expat life, there was not much in the way of workplace / leadership related content when it came to support and resources for the executive leader who was departing a role or title, and even less content to assist The Stayers, and board of director members while navigating the transition of leadership. 

As I launched and formalized Leaving Well, I quickly realized the difficulty of delivering the services I offered in a way that was sustainable. 

In June of 2023, I attended a one-day mastermind in New York, hosted by Arlan Hamilton. Each of the attendees had a hot seat opportunity and when it was my turn, I asked Arlan how I could offer my signature body of work - Leaving Well - alongside interim executive leadership for organizations going through a major transition - while still tending to myself, my rest, and my boundaries. My question wasn’t about scaling for the sake of business growth, but to increase the scope of impact.

Her answer was to share the following: 

“I know very well what it’s like to be very accessible. However, I choose the way I am accessible and choose how to offer my time.. One of the ways you could do this is by choosing the very specific things you do - but not offer them 365 days per year through your consultancy arm. If you desire to spend more of your time at home, then find ways to have your time before, during, after, and in between the work that you deliver, so that you are also replenished.”

During that mastermind, Arlan mentioned that she was planning her first conference, which came to be named Your FIrst Million LIVE, after her second book, Your First Million [purchase your copy on Bookshop or Amazon]. What a joy to have attended in early April 2024, and witness the first of many of events that Arlan will no doubt produce in the coming years.

The conference was incredible and jam packed with an incredible line-up of folks who brought their expertise to the stage from a multitude of vantage points, with powerful nuance, and personal stories.

Throughout the entire conference, I couldn’t help but be impacted by the messages around rest, prioritization of goals and impact, and how you treat people along the way. I saw Gary Vee speak in person back in 2015 and it was delightful to hear him speak again during a fireside chat that Arlan moderated. His vibe has shifted quite a bit in the last decade, to a bit softer version.

Gratitude needs to be the first thing that comes. Chaos needs to be in perspective. It’s all about human beings. 100% of the upside to your business is how you navigate the people around you. -Gary Vee

There were also many correlations from a few speakers about their own experience with Leaving Well. One that stuck out was Lauren Chan, who recently sold her business, Henning, to the massive and very popular clothing company, Universal Standard. It was so powerful to hear her story of leaving that company, and how much the identity of ‘business owner’ was attached to her role. 

[Henning] went to the right place, and I’m so happy with how it went. I had a transitional contract for about a year, so I got to hand it off, and work on some collaborative designs. But more than anything, it was a mental shift. I gained a confidence by having that business card to whip out, it was really empowering. I’m no longer the CEO of my own business. I no longer walk into a room with that being my moniker, and that was attached to my confidence. ” -Lauren Chan


For those who wish to build businesses that can sell, check out the book by a similar name: Built to Sell, creating a business that can thrive without you. (purchase on Bookshop or Amazon).

In the world of Leaving Well, 100% of the upside to prioritizing an intentional workplace transition is how you navigate the people around you as you’re departing, or as a board member how you prioritize the staff during a leadership transition.

Find five things to cancel, restructure, defer. -Camille Nisich

From the stage, Camille walked the audience through a process for staying aligned inside your business or organization when it comes to your finances. Her encouragement was to regularly find five things to cancel, restructure, or defer. This concept was focused on canceling subscriptions, restructuring payment plans, or deferring the purchase of certain items. However, I immediately related this advice to the concept of Leaving Well. 

During workplace transitions, it is important to prioritize those same three things:

Cancel appointments that no longer matter for your remaining time at the organization. Rather than simply canceling, identify someone else in the organization who can take the work forward and make the introduction.

Restructure the way you spend your time as your weeks tick down to your departure. Be very diligent about asking how your time is best served during your last few weeks. Take a look at your draft email folder to find projects or conversations that you weren’t previously ready to complete, and restructure what “done” looks like. 

Defer the projects that you will no longer have time to complete, and instead prioritize helpful knowledge transfer exercises to leave behind with your colleagues (whom I call The Stayers).

Back to a beautiful lesson on the topic of managing your energy expenditure and stress levels as it relates to business, this set of guidelines from Issa Rae resonated when thinking about both my own offerings, as well as the way you might navigate your own decisions re: Leaving Well in your own career:

Everything I do has to fit into a particular set of tenets, with these questions asked first:

  • Does it make sense

  • Is it furthering or progressing my career

  • Does it fit the story or narrative

  • Does it allow me to help in the way I want to help 

The refining process is the best part. -Issa Rae

My favorite speaker delivered the most potent and powerful statement as he was leaving the stage, following his interview. Humble Lukanga …

Show me someone who has achieved a level of success, and I guarantee you they have a long list of things they have stopped. Comparison to others, ridiculous shopping, social networks to stop logging onto, friends to stop associating with. What is your Stop Doing list? No tactical advice will work if you’re not mentally and soulfully ready. -Humble Lukanga


I was so incredibly proud to witness Arlan and her team deliver three days of an incomparable event to anything else I’ve experienced. The genius from the stage was incredible, but the real magic was in the other attendees. 

It reminded me of the first in-person opportunity to spend time with Arlan and brought back – front and center – the reminder that my business needs me to be whole and supported. It’s through relationship, community, and taking advantage of opportunities to be in the room with other folks who are on similar tracks. It’s through prioritizing ways to deliver my work in sustainable ways, where I can be rested.

Be in a constant state of harvest. This matters too much. I am the investment.  -Ange Matthews


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48: Book Recommendations

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46: Workplace Transition Archetypes