Preparing for the ‘Third Third’

INTRODUCTION

The Catalyst Leadership Trust (CLT) is a Samudra community, curated to help Catalyst leaders drive the change needed for the world and for their organizations.  Participants in the CLT are Catalyst executives chosen for their bold strategies, innovative outlook, and proven record of business transformation and community impact. Selected members represent a wide range of industries and roles.  This community is curated and organized as a partnership between Samudra and Catalyst Constellations.

One key benefit of being a CLT member is access to cutting-edge research that explores topics that are chosen by the members. One topic that has emerged in conversations with CLT members, is a desire to better understand how Catalysts navigate the latter parts of their careers and latter parts of their lives. 

For many people, there are at least two phases of their professional lives: early in career as we figure out the type of work or industry we’d like to do and gain related skills, then later in career when we are more established, gain expertise and perhaps move into leadership positions.

Through the years Catalyst Constellations co-founders Shannon and Tracey have noticed that Catalysts don’t seem to move from that second phase into traditional retirement. Instead, they intentionally craft a third part of their career.

We set out to better understand this ‘Third Third’ by having conversations with people who are currently in this period or have been considering this period.

We interviewed seven Catalysts. Three of them are members of the CLT. One is a member of the Women Advisory Trust (WAT). Three are outside of the Samudra ecosystem.

Five Key Insights

  1. We need a new word for ‘retirement’ in the Third Third.

  2. There is often a clear transition point that tells us when to make a shift.

  3. Motivation shifts away from achievement in the Third Third.

  4. There is a lot we can begin to do during our Second Third to make the transition easier and alleviate any anxiety:

    • Engage in thought exercises to intentionally design your Third Third.

    • Reflect on what you are good at and what you love doing.

    • Articulate your priorities and boundaries.

    • Experimentation.

    • Nurture your network aligned with what you discover.

  5. As Catalysts, you needn’t fear, your catalytic nature will guide you!

A Look at Each Insight

We Need a New Word for ‘Retirement’ in the Third Third

Consensus: The word retirement is the wrong word to describe the Third Third. Ways the ‘R’ word was described: annoying, a distraction, demeaning, stigmatizing.

This group of Catalysts has no intention of moving from their Second Third into a traditional version of retirement:

“The thought that people would think that I was sitting around reading Scandinavian murder mysteries all day? I don’t like it! ... I am turning work away. If I were 40 right now, I would build a company and I'd be making tons of money. I feel like I'm at the top of my game right now. I have so much experience, skill, curiosity, and resources I didn't have. That is gold. Why would I walk away from that? I mean, it’s fun. I made a decision to only work with people I want to work with!” - Virginia Hamilton

More than an annoyance, there is a feeling that being labeled as retired communicates to your network that you are no longer looking at new work opportunities – which is seen as detrimental. Because of this there is a need to control the use of the word ‘retired’. For example, having your company post that you have retired has the potential to limit opportunities that come next.

For some, the movement into the Third Third has been more of a continuum than a hard break – for example adding more volunteer work, or moving between a focus on passion work and paid work, depending on the bank account.

Some markers of the Third Third: moving away from full-time roles, engaging with a variety of organizations and challenges as a portfolio, and becoming more selective about the type of work and with whom (stop doing work I don’t want to do anymore!).

New words that folks are testing for themselves: self-employment, post-operating career, Kat 2.0. Common titles and roles include Advisor, Board Member, Consultant, Venture Partner, Mentor, and Executive in Residence.

There Is Often a Clear Transition Point That Tells Us When to Make a Shift

For most of those interviewed, there was a pivotal moment that created a break from the Second Third.

Shifts in working conditions, specifically a change in or conflict with leadership, leading to *intense* burnout, was a shared experience for many. This deep level of burnout moved people into a period of self-reflection and led them to realize there needed to be a bigger change than just jumping to another job.

“I was burning out and finding I didn't have a supportive relationship chain above me; they didn't have my back. I had lost the drive to try to achieve. It was time to step away.” – Susan Ehrlich

Other key events that led toward the Third Third: achieving a milestone where institutional benefits were available, the death of loved ones, and a spouse requesting a less intense schedule of their partner.

“I don’t have the pressure of having to achieve in some particular career vein. I feel completely disengaged from that and look at it as a kind of weird curiosity. I don't feel the pressure of having to be part of a productivity scene. I don't at all feel like I need to prove myself. I'm just not motivated or ambitious in that way. And it's not that I don't want to work that hard. … This is giving me a more reflective period of my life. I feel like it's the same experience I felt in my early twenties, but I have a lot more resources.” – Ann Kovalchick

Motivation Shifts in the Third Third

If our Second Third is about operational achievement, which we can measure in organizational KPIs and scorecards, motivations in the Third Third seem to shift.

Motivators that have become more important include learning, exploration, maintaining relevance, focusing on personal strengths and interests, having a meaningful impact with causes that matter individually, to organizations and directly at the 1:1 level. While money was not a primary motivator, there is still motivation around money.

Learning, Exploring, Doing New Things

Learning is a primary motivator for everyone interviewed. Catalysts are curious learners by nature and this seems to follow us through every stage. “I love to learn” was a sentence heard in every interview.

And while Catalysts can learn in any situation, there is a stated desire to push past what had been done before and experience new organizations, new problems, and new people – without having to be responsible for everything, not having to do what is required, not having to do the work that they no longer want to have to do.

Plus, every person explained the love of getting to work on multiple things at once, getting to be “intellectually promiscuous” by building a portfolio of engagements.

Maintaining Relevance

Four of those interviewed talked about the motivator of staying relevant, each sharing stories of having watched colleagues around them have their experiences become irrelevant.

“I fear massively irrelevance and decay. Decay not of me, but decay of my knowledge brain. I've watched a lot of board members, this is a reason I don't want to be on public boards, they're just talking about the old days instead of actually knowing what's going on and staying current. And I don’t want to be one of those people.” - Karenann Terrell

“I have on my golf balls a Latin saying that gets misinterpreted as ‘between a rock and a hard place’. It's not what it really means. Literally, it means ‘in front of me a precipice and behind me a pack of wolves.’ And what it was originally used for is to say that life has all kinds of obstacles. Everybody bumps into obstacles and precipices over time, but if you stop, and you don't keep moving forward, there's a pack of wolves behind you that's going to get you. The saddest people I know stagnated and got stuck. It's just horrible to see. After they fell in the precipice, they pause and stay there. And nothing happens. … The most flavor in life comes from challenge. No one feels flavor from the couch and daytime TV.” - Toby Eduardo Redshaw

Focusing On Strengths & Interests

Every single person sounded gleeful as they talked about the ability to only work in areas where they can apply their strengths, that they are personally interested in and with people they like.

Identifying opportunities that align with strengths and interests is an iterative process of exploration.

“I check in with myself and ask ‘Do I like this? Do I not like this?’ I’ve learned that I really like kettle bells, not weight machines. I like trail running, not pavement. It is similar in my work. I love to do executive coaching; I love doing mentorship. I test things out and ask 'Does this work for me?' I cast a very wide net. I set things up intentionally, as shorter engagements, with people I know and trust. Not all of them have worked out – I was a startup advisor and they didn't know how to use me. There have been a couple of engagements like that. You begin to go to situations being very clear about what you want to help with and where you can add value.” – Chris Cravens

Meaningful Impact

Aligned with focusing on areas of interest, several folks shared that one of the ways they choose what to work on is whether or not it is aligned to the impact they’d like to make. 

The impact that matters is unique for each of them. For one person it is working with organizations that have a true belief in diversity and inclusion. For another, it is a deep focus on climate change. For another, it is stepping into roles with organizations where she can see her ability to add value and leave things better than she found them.

For several of those interviewed, there is an increased desire to make a direct difference, 1:1, in individual lives.

“One of my best friends, that was not even 60, died in August. I had a wonderful, incredible experience of being with that friend in the last 6 weeks of life. At the end, it is just us. You and me. Loving people. And making contributions. It is not all the shit that we have and the titles that we have. It is just people. What I feel like I can continue to do is have an impact on individual people. A woman came up to me after my last class and said the class completely changed her life. That is the motivation for me. I have been trying to change big government systems for 40 years. And some of them look the same. So, I am learning it is the individual impact I can have with individual people, rather than claiming the big work I got done or having a fantastic job with a great mission and title. It is moving from top down, to side by side - networks as opposed to hierarchy.” – Virginia Hamilton

Money

While money does not seem to be a primary motivator in the Third Third, there is still motivation around money in a variety of ways.

For some, retirement from a financial perspective is not an option. Therefore, engagements that make significant money were still important. For some, the current state of the bank account would direct whether it was a period more focused on money-making projects, or more-passion projects. One person shared that her cancer has returned, and that has led her to think about passive income that can sustain her.

Others shared that because we have no idea how long we will live, it is difficult to feel confident living solely off of savings. Therefore, making enough to pay basic expenses, like rent and healthcare, feels important.

Money also plays another role – communicating our value. If choosing to participate on boards or as an advisor, “money is a scorecard and when you do things for free it becomes an expectation.” So being clear about what your rates are, when doing work with organizations that can pay, is a way to quantify the value you still bring.

There Is A Lot We Can Begin to Do During Our Second Third

Van Ton-Quinlivan is the one person we interviewed that is still in her Second Third and she explained that she is nervous about the path to her Third Third

“I think it would be scary if you kind of fall off the cliff. The day after you stop working you lose passwords and access – it seems like a very binary experience. You get cut off from that identity. And if you don't begin paving the path, then it's too dramatic. So, part of me is trying to figure out ‘what is satisfying, but not a full-time commitment and doesn't bring the same level of stress, but yet it's still impactful.’ … it's hard to take the type A out of the type A, to take the Catalyst out of the Catalyst. And so, what am I going to do in that third age? That's why I've taken up my taiko drumming.” - Van Ton-Quinlivan

Those interviewed shared four key activities we can begin in our Second Third to help the move to our Third Third feel more like a continuum than a cliff:

1. Engage in thought exercises to intentionally design your Third Third

Virginia has been teaching design thinking across the US government for decades, so it is not surprising that she shared that preparing for our Third Third can be approached as a design problem. Here are some of the reflection exercises / design problems that people suggested:

  • Imagine yourself at an old age, with one grandkid sitting on your knee, and he asks you: ‘What did you do in life that we care about?’ – For Toby, telling him that he ran labs or moved a population from 4G to 5G probably wouldn’t matter. So now he is deeply focused on the environment. Once we identify key areas, we can begin to do more of that work with intentionality.

  • Try to get to know your 90-year-old self. What might she need to support mobility? To support engaging with the world? Consider: If I were to meet my 90-year-old self, what would I begin doing now that would lead to her hugging me and not hit me over the head and say I screwed up? – For Virginia, this has led her to build a smaller residence in her yard which will allow her passive income from renting the bigger house she now resides in, plus it has no stairs to accommodate a walker or wheelchair.

  • As we age our worlds can get smaller. How might I continue to make my world as big as possible? – Virginia watched her parents' lives move from travel and people to a small scope. To have her trajectory be different than her parents she reads new books, takes classes, intentionally builds relationships with younger people, takes full months to do language immersions and is planning to travel via VR if necessary.

2. Reflect on what you are good at and what you love to do.

Because a primary motivation of the Third Third is having the ability to focus on work that leverages our strengths and passions, it is crucial that we identify our strengths and interests.

As an easy way to identify strengths and passions over time, Toby suggests creating a ‘future box’: have a cardboard box, and every time you feel great about something or something really interests you, write it on a paper, date it, and put it in the box. In the future, you can sift through the notes and see what motivates you and interests you and the type of work that most excited you.

Ann suggested considering what you loved in your youth. She likened the Third Third as allowing her to come full circle, going back to the reflective period of her 20s as she entered her First Third, however now she has more experience and resources. She is revisiting the things that excited her 20-year-old self, and seeing what is worth exploring more now.

Several people spoke of the benefit of having worked with an executive coach to help identify strengths and passions – in part to ensure time is dedicated to this reflection during the bustle of the Second Third.

3. Articulate your priorities and boundaries.

Several people had a clear list of what was important that had been evolving for some time. They suggest giving yourself permission to begin to consider what might be important and creating a place where you let yourself write them down.

For example, Ann knew that she wanted to move so she prioritized opportunities that would support a nomadic lifestyle as she and her husband explored new locations. Susan was clear when exploring opportunities that they would be compensated, not full-time, fit with her skills and experience, provide opportunities to learn, and allow her to stay local. And Karenann prioritized working with organizations that focused on diversity and inclusion and a clear track record of courageously working toward a strong vision.

4. Experimentation.

While several folks hadn’t begun to deeply consider their Third Third until it had begun, you can begin to experiment in your Second Third. For example, Van had a love of music in childhood; she was an accomplished pianist. So as a small step of integrating a former passion into her Second Third, she has begun to study a new instrument – taiko drums. 

For Susan, she had an interest in serving on boards and in venture. She began to do both during her Second Third, and this experience led to many opportunities in her Third Third.

5. Nurture your network aligned with what you discover.

It is never too early to cultivate a network that can support your Third Third. 

For all those interviewed, opportunities they are engaging in came through their networks – for some, opportunities came in response to their posts on LinkedIn and, for all, opportunities arose through conversations with folks in their networks.

If you have colleagues that are in their Third Third, ask them about their experiences. A conversation like this was pivotal for Susan.

And as you identify your potential interests, reach out to folks that align. For example, if you are interested in serving on a board, have conversations with board members of your organization, or reach out to folks that you know have served on boards. Karenann reflects on her gap in doing this. This is her key piece of advice to others now. 

“If you have done a good job of networking, the opportunities will knock on your door.”  - Toby Eduardo Redshaw

As Catalysts, You Needn’t Fear, Your Catalytic Nature Will Guide You!

If your Second Third feels all-consuming, not to worry - your catalytic superpowers of creative problem-solving can be used to design your life whenever you are ready to begin! Take Virginia’s words to heart:

Our Guides

Here is a snapshot of the experiences and wisdom from each of the people we interviewed.

  • Ann Kovalchick

    Second Third Overview - Ann spent 30 years working in higher education as an IT leader – in several CIO roles, spending the last 8 years of her Second Third as the CIO at the University of California Merced.

    Snapshot of Third Third - Ann is in a period of experimentation – moving to various cities to identify a new home and trying different roles, currently working as a consultant with KPMG and as the Chief Data and Learning Officer for the nonprofit Up Together.

    Process for Identifying Third Third Opportunities - Ann wanted to expand beyond higher education, so she began a process of ‘trial and error’, having conversations with a lot of folks and taking roles that don’t have to be long term that felt resonant, with the primary goal of learning, vs producing.

    Advice about Third Third - Try to make a clean break from the Second Third. “You have to decide if this is evolutionary or revolutionary. It is hard to do both at the same time.” And try not to take it too seriously – find a flow.

    LINKEDIN

  • Chris Cravens

    Second Third Overview - Chris describes this period as an “intense application with skills developed around operational excellence, change management, program management and gettingshit done, focusing on companies that scaled fast.” This included roles such as CIO at Uber & Zynga, VP of SW Engineering at Splunk.

    Snapshot of Third Third - Today Chris serves as a Strategy Consultant, Executive Coach, Advisor, Startup Mentor and Investor across a variety of organizations.

    Process for Identifying Third Third Opportunities - Chris made a conscious decision to treat himself better than he did in his Second Third. Today he is committed to casting a wide net and testing roles, then asking ‘Does this work for me? How do I feel? Do I like this?’ He sets up short engagements in areas of interest with people he knows, likes and trusts.

    Advice about Third Third - Be thoughtful and intentional about the outcome you want for your Third Third. And be willing to adjust and fail.

    LINKEDIN

  • Karenann Terrell

    Second Third Overview - Karenann sought assignments around transformational technology during periods of tumult across her operating career, which was scary and brought her great joy. Roles include CDO & CTO at GSK, CIO at Walmart, Baxter Healthcare and Mercedes.

    Snapshot of Third Third - Karenann has built a portfolio where she serves on multiple boards, including the Google Cloud Advisory Board, and as an Advisor to multiple companies. Her areas of focus are diversity and inclusion, helping women reach senior positions in tech, helping companies that are scaling up or being disrupted. She is still incredibly busy and has an EA and research assistant to support her work.

    Process for Identifying Third Third Opportunities - Opportunities came to Karenann, so she has had to build a process of what to say yes and no to. Her main criteria: interesting people with interesting problems – not one without the other. She has made some mistakes where one or the other wasn’t present, and she’d stop those engagements.

    Advice about Third Third - The nature of the Second Third is complete engagement and achieving your potential in an operating world may preclude you from thinking forward. And that can be OK. But ideally begin to cultivate a network that will support your interests. And once in your Third Third, find cohorts of non-operating leaders, like at Samudra. And it’s OK to get the help you need!

    LINKEDIN

  • Susan Ehrlich

    Second Third Overview - Over the course of her second third, Susan was a C-suite executive (CEO at Earnest, CFO at Simple Finance, President of Financial Services at H&R Block and Sears Holding) with 25+ years of experience scaling financial technology businesses, teams and products.

    Snapshot of Third Third - Susan has built a portfolio where she serves on multiple boards, including BECU bank, and as an Advisor with multiple companies and a Venture Partner. In addition, she works in her family winemaking business, and joined a private club to pursue her passion of golf.

    Process for Identifying Third Third Opportunities - The process started with a LinkedIn post to her network. Her employer had “retired” her in the headline of their announcement of the appointment of a new CEO. She made the story her own and put the word out to her network that she was looking for opportunities. That post received over 30K views and opportunities started to filter in. Susan is clear that her portfolio work should not be full-time, should fit with her skills & experience, provide opportunities to learn and allow her to stay in the Bay Area.

    Advice about Third Third - Communicate with your network about your intentions and what you want – “Put it out there into the universe and see what comes back to you. You may be pleasantly surprised!”

    LINKEDIN

  • Toby Eduardo Redshaw

    Second Third Overview - Toby served as an executive at multiple organizations, such as Global CIO at American Express and Aviva; SVP and CVP of Innovation at Verizon and Motorola and VP of Global Supply Chain Integration at FedEx, as well as “taking a run” at Silicon Valley startups, usually choosing roles where there is the biggest mess he can help clean up!

    Snapshot of Third Third - Toby describes his move into the Third Third as a trajectory vs a moment. While he was an executive, consulting opportunities began to “arrive.” Over several years he steered more toward opportunities based on the intersection of what he loves and what he’s good at. And his choices changed to include what was important to him societally and socially – which for him has an emphasis on climate. Today he is an Advisor to multiple organizations, serves on multiple boards, is a Mentor, Executive in Residence and a Venture Partner.

    Process for Identifying Third Third Opportunities - For Toby the Third Third has been a process of evolving toward work at the intersection of what he is great at, what he is passionate about and what he believes is meaningful. Sometimes he will be doing more volunteer work, and then he will realize the bank account is low and will need to move toward paid work.

    Advice about Third Third - Make sure you are really good at networking. Networking is simple – your job is to be helpful and useful. As you make life changing shifts, bringing your network with you is hugely valuable. “A semi-retired person with a fantastic network has lots of choices.” And keep moving forward!

    LINKEDIN

  • Van Ton-Quinlivan

    Second Third Overview - Van is currently in her Second Third with 15+ years in workforce development, currently serving as CEO of Futuro Health which is in the process of a multi-state expansion. While she can easily imagine another 10 years with Futuro, she does not want to fall off a cliff into her Third Third, so she is beginning to explore interests and opportunities that may make the transition feel natural. She has taken up taiko drumming and is exploring the Harvard Leadership Institute for career changers.

    LINKEDIN

  • Virginia Hamilton

    Second Third Overview - Virginia held increasingly influential positions in government, leading to becoming a Regional Administrator in the US Department of Labor and advisor to the Obama Administration, and teaching government employees across the US to leverage human-centered design to ensure that the people being affected by policies and programs are involved in the design of them.

    Snapshot of Third Third - Virginia continues to work as a public sector innovation catalyst, consulting with and advising organizations on how to infuse design thinking into how they work with more work than she can take. She has a grant to ‘Scale Virginia’ so that the human-centered design classes she taught to federal employees for decades can be replicated without her. She has an idea for a product she’d like to create and is excited for AI to help her jumpstart it. Her breast cancer has returned for a third time so she has been battling insurance companies and documenting the issues. Once her treatment is complete, she plans to publish her experiences. She is building a cottage in the yard as an income source now. And once the time comes that a big house with stairs doesn’t fit, she plans to move into the cottage and rent out the big house.

    Process for Identifying Third Third Opportunities - For Virginia the Third Third is a continuation of work she has been doing, but now as a consultant and only working with people she likes working with and what catches her interest. In addition, she has a drive to document what she has learned to pass it on to others.

    Advice about Third Third - Frame your Third Third as a design problem, making friends with your 90-year-old self. Lean into this time with curiosity, a love of learning and a sense of humor. Cultivate friendships with people younger than you. And as Catalysts you don’t need to worry - your catalytic nature will guide this transition!

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