• Judi Cunningham

What Comes Next?: Family Enterprises and Navigating the Challenges of Uncertainty

Over the course of the last year and a half, we have seen remarkable shifts in corporate culture, not least that conversations about mental health and how we feel about our work have begun to take a more central role for companies.


How we work and where we work has changed more than anyone could have predicted when we celebrated the onset of 2020. We have cobbled together at-home workstations and become experts at Zoom, GoogleMeet, Webex and Microsoft Teams. We have dealt with the logistics of having multiple family members working in the same spaces and diverting our children’s attention for long enough to get through this meeting or to complete that task. Big companies, previously hesitant to allow work-from-home days, were all forced to find out if their fears about decreased work output were warranted. Where we may have once described our business travel as essential, we have better learned what we can – and cannot – do virtually.


In their at-home work spaces, people who are not members of enterprising families may have never had their families closer to their professional lives; for members of family enterprises, some of the primary skills in navigating the overlaps between family and work have certainly been put to the test. At the same time, conversation and consideration about our emotional fatigue, general stress & anxieties, and overall mental health have begun to figure more prominently in corporate discussion.


But these conversations are not brand new for enterprising families: rather, it has always been impossible to remove the emotional, interpersonal realities from professional spaces in family enterprise contexts because of the inherent “familyness” of work. It is precisely because of this deep familiarity that family enterprises are poised to lead us forward, offering much-needed guidance on how to balance the professional with the personal, and the emotional with the workplace.



The Emotional Fallout of Carrying On

I have been thinking about families a lot as we approach the end of another summer amidst continuing uncertainty. Despite some warning signs, many companies are beginning to transition back to their offices and both personal and professional travel seems to continually increase. While many of us have been anticipating a return to “normal,” it seems that we will need to get comfortable with the certainty of uncertainty. As we approach a new season in this COVID-era, we will naturally begin to address some important questions: What parts of COVID-19 reimagined work will we integrate, and which will we begin to transition away from? What will this mean for all of us emotionally? What tests will we be put through as the economy continues to cycle with these changes? And how will the skills of enterprising families become especially relevant in this context?


The answer to the last of these questions is already becoming clear. There is a natural melding of commercial pursuits and interpersonal conversations in enterprising families. For all who are or have been in this world, either as members of business families or as those that work closely with them, a key challenge and a pivotal strength lies in this intersection of business and emotions. As we continue to ride the waves of new COVID variants, it looks a lot like our family-lives will remain close to our work lives - and those outside of the family enterprise space may have to continue to get comfortable melding their families with their professional lives.


As we wonder what the world has in store for us as we close in on the last quarter of 2021, what most are in agreement around is that everyone will feel differently about opportunities to come back together and increase our contact with others. Some will feel a great deal of anxiety about the sudden pull to socialize or work in-person; others may feel eager and impatient for the same. Regardless, many of us will exist in varying states of grief - from grief over the loss of the quiet, less intense lives we lived while under restrictions, to grief over the loss of the way that things once were, and for all of the states in between.


These discussions bring to mind a common and important tension that has been a reality for many of the families I have worked with throughout the last year-and-half: namely, our differing experiences of risk, and navigating the tensions of contradictory boundaries. In the slowing down of our lives, I have had numerous conversations with members of business families about where and how their family members have done things that they disagree with. For some, there has been pain because they have been apart, and disagreement on that distance; for others, watching their relatives disregarding or ignoring restrictions has created other tensions to navigate. Inside of families, some are vaccine supportive and others are against. Navigating these points of diverging opinions is no small feat.


Now, as workplaces are reopening across North America, those boundaries and tensions are becoming relevant across professional spaces. Families in business are particularly well-positioned to address the emotional implications of moving back into the workplace. Afterall, they have been working to address these questions since long before COVID-19, and they have had to consider them in relation to our work all throughout the numerous periods of pandemic intensification.


Adaptability in Enterprising Families


Regardless of the broader-scale dimensions of our pathway forward, it is notable that I have already fielded requests from many of the families that I work with for a return to face-to-face meetings. Even though most of us have figured out how to do many things online that we had never considered before 2020, there are those who desire to come back to in-person connection as soon as we can.


As we face conundrums about how and when we step back into old routines the question remains: how will we begin to negotiate our varying states of comfort? And, for that matter, do we want to return to the same patterns we abruptly left behind in the spring of 2020? If we apply compassion for our various stages of discomfort or grief in our re-entry we may also have to reassess the configurations of our work altogether. Enterprising families can, once again, offer leadership in this realm. Navigating atypical work relationships, incorporating personal needs, values, and desires into workflow, and addressing tension and conflict are not foreign to families that run businesses and/or manage other assets together.


As families begin to consider how they will approach the relaxation of work and life restrictions, they can continue to provide an example to the wider commercial realm. The very reality that makes combining family with economic pursuits so challenging and so rewarding, will only be amplified over the course of the next several years.


The Certainty of Uncertainty


If there is anything we can rely on now, it is that nothing is certain. The future will likely remain unclear for a long time coming.


We will all face challenges, but enterprising families – particularly those with robust support systems and processes for managing conflict, decision-making, and challenges – are especially well-positioned to adapt, create new visions for a different kind of future, and integrate varied and sometimes-contradictory boundaries and desires for pathways forward. Regardless of the skills we have coming into this, or what we are quickly trying to learn as things come toward us, it will be crucial for us all to get comfortable with our discomfort, and be prepared to weather uncertainty for the foreseeable future.


This does not have to be a dire warning. Rather, it can remind us of our resilience and adaptability. We have models and examples for ways to not only survive, but thrive in this new reality. Families are some of the most resilient systems that exist. They offer models for how to adapt and adjust to unforeseen changes and how to persevere through adversity. The family system itself is a reminder about the stubborn human desire for connection and closeness. As we begin to accept that we just can not predict what lies ahead, I think of the reminders we give to families everyday: look to your support systems; insist on continuing difficult conversations; and commit to maintaining ties and connections through tension and misalignment. As many enterprising families can attest, even the most challenging of messes have pathways to a better future.





Judi Cunningham founded the Telos Group with Mike McGrann in 2019. She is passionate about family and business and has dedicated her career to helping family enterprises thrive. With a holistic view of the needs of family enterprises, Judi facilitates alignment and decision-making processes with strategic thinking and adept facilitation. With a Masters degree in Family Systems Counselling and over 20 years consulting with complex family enterprises, family offices and professional advisors, Judi is a creative & deep thinker.


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