Running a team, an IT practice, or an entire organization can sometimes be a lonely job. I myself had a few reality checks this year operating at the crossroads of decision maker and content expert—a space that most IT leaders know all too well. 

As we close out our second year at Tuckpoint Advisory Group, I find myself reflecting on a journey marked by scaling pains and, at times, burnout and overwhelm. 

In that spirit, I’m sharing three actionable insights you can put into practice to scale more smoothly and navigate the sometimes lonely road of leadership.

Three Actionable Leadership Insights for Scaling More Gracefully and Feeling Less Alone Along the Way

1. Expect Everything, Everywhere, All at Once (But Don’t Panic) 

Have you ever tried to bring order or modernization to one area of your organization without touching other areas? It feels like pulling the thread on a sweater only to watch the whole thing unravel. 

Such is the nature of growing and scaling pains, especially within transforming organizations—you can’t fix one thing without treating other interrelated problems.

I felt this on a seismic level in 2024 within my own business, where we saw significant growth that surpassed my original goals. It was exciting, but it was also a reality check because the size and scope of projects, number of consultants, and number of engagements exploded all at the same time—and with that growth came new challenges and problems.

My first response was to compartmentalize by tackling one issue at a time, but I quickly found that all the challenges were interrelated. So, I gave the thread a tug and decided to go all in on a systemic approach rather than focusing on one symptom at a time.

In hindsight, I had to laugh a little at how long it took me to remember this concept. It’s literally what we do at Tuckpoint! Usually, a client will call us and say, “hey, our product teams aren’t getting it and we need you to fix them!” Upon further examination, we always uncover a slew of interrelated issues that also need to be addressed to “fix” the product teams. When we pull the thread on the sweater, we find that the engineering context, leadership behaviors, roles and responsibilities, and other areas also need tune-ups. 

As a result, it can often seem like you're trying to solve everything, everywhere, all at once. The feeling of “being in it” may never entirely disappear as you navigate transformation, scaling, and growth. However, we leaders can do our best to become more comfortable with it. 

When you resist the urge to compartmentalize and, instead, embrace transformation and scaling as an ongoing, iterative process, you gain a heck of a lot more peace of mind. 

To put this into action right away, try to shift your mindset around change. Can you re-frame constant change from something you need to fight against to something you can flow with? Take a more zen mindset and see how the universe connects all things, and how taking a systems-thinking mindset might help you solve multiple issues at once. 

2. Seek Counsel and Build Your Bench

Transformation can be a lonely endeavor for leaders, especially if people expect you to have all the answers. All. The. Damn. Time. And being in a state of constant change can feel really uncomfortable and overwhelming. 

I definitely had my own run-ins with overwhelm and burnout this year as I navigated Tuckpoint’s scaling pains. Truly, I could not have survived it without seeking counsel from trusted advisors.

And I’m not talking about quick or generic advice—I’m talking about partnering with experts who could embed themselves within my org to understand the level of nuance required to make recommendations for meaningful change. 

So, here’s my advice to you, dear reader, in case you’re navigating transformation for the first time, or are simply feeling discouraged by how nonlinear the process of scaling has been: Seek help by surrounding yourself with people who have solved your problems before. 

Start by building a support network of knowledgeable advisors who can offer meaningful, context-specific insights. Then, give them the grace and patience required to wrap their heads around your issues so they can really give you the support and advice you need. This investment is so worthwhile and can often be the key to navigating transformational challenges without succumbing to overwhelm.

3. Don’t Forget to Celebrate Milestones Along the Way

During periods of high growth, it’s easy to focus on “what’s next” rather than acknowledging and celebrating achievements. In contrast, during periods of high uncertainty it can be easy to fixate on the issues rather than the small wins. 

I know that you’ve likely gotten to where you are today by focusing on the climb ahead. This year, I learned the hard way that you also need to stop and enjoy the view. It’s important for your own mental health and it’s also critical for team morale—your people are looking to you to hear that their individual and collective hard work has paid off. You don’t always have to pop champagne, but you should at least take a breath and take a pause.

I struggled with this in 2024 as recently as September when Tuckpoint hit a big milestone. And do you know how I responded? By thinking, “where do we go from here and how do we maintain it?” (It's no wonder I’ve been feeling burnt out.) 

I invite you to join me in cultivating a gratitude practice by stopping to reflect on progress (both for the sake of team morale and personal resilience as a leader), and to get better at sitting in celebration. 

Not sure where to start? Try integrating regular moments of recognition into your operations. Host post-mortems after a big milestone, give team shout-outs to award credit where it’s due, and think about popping a bottle of champagne (or sparkling cider) every once in a while. You might find that holding space to celebrate others will help you better enjoy the view, as well. 

Parting Thoughts

I know all too well how easy it is to get caught up in the churn—whether you’re navigating operating model transformation or trying to convince your peers to step into the future with you. But growth doesn’t have to be a lonely, overwhelming process, especially if we can learn to adopt new mindsets around change and stack our bench with experienced counsel. 

If you’re interested in more leadership-forward insights (with a heavy side of commiseration and solidarity), I invite you to join my newsletter community to receive a once-a-month note from yours truly. Sign up here.