Practical advice and perspective from a leader who’s been there — and found peace on the other side of pressure.
It seems I’m having the same conversation with peers, clients, candidates, and friends every week. They’re struggling with the “middle squeeze” of their careers. They’ve moved beyond the early years of proving themselves, but now they’re leading teams, raising kids, managing bigger responsibilities, and trying to hold it all together. The demands of work and home can start to blur, and suddenly they find themselves asking, “Am I doing this right?”
A few months ago, I was having lunch with my friend, Rob Buck, and we got to talking about this very thing. Rob is a successful and well-respected CFO at a major healthcare company with more than 30 years of experience in healthcare finance and operations. But what first drew me to him wasn’t his title or résumé — it was his humility. I actually met Rob about five years ago when he was serving as a greeter at my church. Since then, I’ve come to admire not just his leadership, but the way he lives it out — anchored in faith, grounded in family, and genuinely present in the lives of others.
Now in his 60s, Rob has the kind of perspective you only gain through experience. I asked him to share a few lessons he’s learned over the years—things he wishes he’d known when he was in that “middle squeeze” season of his life. Our conversation was honest, insightful, and filled with encouragement for anyone trying to navigate this stage of life and leadership.
The Wisdom of Experience: Practical Advice for the High-Pressure Years
1. Looking back, how did you decide where to invest your time? If you could give your younger self a simple rule of thumb for managing work/life balance, what would it be?
I got married at 35, and my daughter was born when I was 40. Around that same time, I started working for a large, fast-paced healthcare company with unlimited professional possibilities. It was a true turning point — becoming a father while trying to advance my career was incredibly challenging.
At first, I struggled to balance both. I had high expectations for myself in every area, and both work and family seemed to require endless hours. But I was determined to find a rhythm that allowed me to be present in both. My company was flexible and family-friendly, so I started shifting things around — attending the important family events and making up the work time at night or on weekends.
To my 40-year-old self, I’d say: don’t miss the moments that matter most. For example, I love photography and have about 50,000 pictures on my devices. Looking back, the ones I cherish most aren’t from work — they’re of family memories. Go to as many gymnastics meets, dance recitals, and games as you can. You won’t regret it.
2. What was your most effective strategy for managing the internal stress and chaos of a high-level corporate career, and what did you later realize wasn’t worth the anxiety?
Managing stress in a demanding corporate environment has always been tough. Early in my career, I tried to do everything myself. I worked 60+ hours a week for decades because I felt like I couldn’t leave anything behind. But over time, I realized that the more I did, the less others had the chance to do.
As I got older, I learned to use a helpful framework to ground myself and control the chaos:
- Get clear on what’s being asked of you. Make sure you have a clear listing of everything being asked of you. Understand the amount of effort necessary. What does success look like? What will it take to get there? This allows you to organize dozens of potential ideas and requests into a streamlined process. For example, I probably have a list of 30-40 initiatives that we are considering. But I have a firm understanding of what is required for each of them.
- Prioritize by value. Look at which tasks actually create the most value for your company or organization, and focus your team’s energy there. Whenever someone comes up with a new strategy or idea to test, I try to say “yes,” with the recognition that we only have resources to focus on one or two at a time. I highlight the ten ideas and then collaborate on which ones are worth investing in first.
- Delegate with intention. Once you know what needs to be executed, utilize all resources available. Knowing people’s skillsets and what will help them grow individually is essential. I think about who I want to delegate to and what is already on their plate as I lead the team.
When I have a clear vision built by these three items, I feel confident I am working on the right things. I don’t let the little things stress me out and realize it is okay to leave some things behind.
3. Many leaders also hit a point in their careers where success depends less on what they do and more on how well they develop others. What helped you make that shift from doing the work to leading people?
It took me time to let go of the day-to-day analytics and hands-on work. I was afraid of overwhelming my team.
That changed after a leadership review when a company president asked me, “When will your team be ready to take your job?” It stopped me in my tracks. I realized I needed to delegate more intentionally.
4. That sounds like a powerful challenge. What was the hardest part of actually handing over the keys? Did you use any tactics to know they were truly ready to handle that increased responsibility?
I was afraid I would make people implode if I delegated too aggressively. I did not want people to “sink” if I threw too much at them. So, I sat down with them on the front end. I let them know that more was coming their way. I told them, “You haven’t done anything wrong, but I’m going to start giving you more.”
As a leader, I gave them confidence that I believed they could do it. They really rose to the occasion and I quickly found out they were craving more responsibility.
I still use that principle today. People can raise their hands if they are taking on too much. Once I knew people wanted more and could handle it, it was easier for me to let go.
5. That’s really interesting. When you think back, were there other mindsets that shifted the way you delegated responsibility and led your teams?
Early on, I thought speed was everything. I wanted to make decisions quickly and move on to the next problem. Over time, I learned that good decisions require perspective by really looking at things from all angles. If you make a decision about a problem too quickly, you could create an even bigger problem down the road.
Building consensus matters, too. Your success is contingent on the commitment from your team members or other stakeholders. When people understand a decision and buy into your vision, execution becomes a lot smoother.
6. Leading at a high level can take a real toll. What helped you stay grounded and keep the pressure from following you home?
A few simple principles have made a big difference for me:
- Don’t take things personally. Work hard, work smart, and be kind.
- Keep the big picture in view — don’t chase perfection.
- Do your best to not let the pressure bubble up and spill over on anyone.
You also have to know your “why.” After COVID, I think we’ve all reevaluated what’s important. I used to work from 7 a.m. to 6 p.m. every day. Now, I focus on being fully present when I’m working and fully present when I’m home.
Work matters. Helping your team matters. But the real question is: what matters most to you? There’s no single playbook for success. What worked the last 30 years might not work the next 30. If you have an idea of what is most important to you, and what is enough, that can help guide your next decision.
7. If you could boil it all down, what’s the one piece of advice you’d want your younger self — or any mid-career leader — to remember?
Give yourself and others grace. Every day won’t go as planned. You’ll make mistakes. Learn from them and keep going.
Treat people with compassion and do your best. Do things the right way. And above all, remember who you’re serving.
Your Success is Not Measured in Photos from Work
After our conversation, I kept thinking about Rob’s comment about the pictures on his phone… how the ones he cherished most are family memories, not photos from work.
Conversations like this remind me why perspective matters. Rob’s story isn’t about perfection — it’s about purpose, priorities, and progress. It’s a great reminder for all of us in the “middle years” that success isn’t just about climbing higher; it’s about becoming wiser.
So wherever you are in your career, take a deep breath. Give yourself grace. Keep growing, keep learning, and keep showing up — both at work and at home. That’s the kind of success that lasts.
#########
About Rob:
Rob Buck is an experienced C-level executive known for leading major organizational transformations across three decades. He began his career with foundational degrees in Finance and Accounting, which fueled his highly analytical approach to business challenges. Rob successfully navigated roles from Financial Analyst to CFO, managing large-scale operations and driving financial performance for organizations with vast provider networks. He is a strategic leader responsible for creating company-wide strategic agendas and managing complex acquisition activity. As CFO, Rob specializes in developing powerful operational reporting and analytics that guide business decisions, combining his passion for financial integrity with practical, hands-on leadership.