Observations from a career spent in the room.
Unfiltered text on leadership isolation, sudden liquidity, and the cold reality of corporate transitions. No performance. No clichés.
The Trap of Proximity: Why Your Internal Network Can’t Offer Objective Counsel
- Your Board has a fiduciary duty to the shareholders and the enterprise value, not to your personal equity or peace of mind.
- Your Executive Team is quietly calculating how your sudden departure or transition will impact their own titles, security, and political standing.
- Your Family Members are naturally flooded with emotional anxiety about your future security, your lifestyle, or the sudden redistribution of wealth. Because they love you, they cannot offer the cold, strategic distance required to navigate a messy business transaction.
- Your Industry Peers are often forced to take sides to protect their own commercial relationships, turning a private dilemma into a public political campaign.
Rejecting the Either/Or Dilemma in High-Stakes Corporate Strategy
Someone said it to me years ago and it stuck: stop forcing yourself into either/or.
His point was simple. Most of the time when you think you’re facing a choice between this or that, you’re not. You’re just not yet seeing the path to both.
I heard it constantly in my sales career, and said it myself more than once: Does the organization want me to take care of my clients or go after new business?
Wrong question. That’s like asking whether you should be a good spouse or a good father. There’s only one right answer: you figure out how to be both.
The either/or framing feels like it clarifies things. It doesn’t. What it actually does is send you looking for someone to blame for having to choose. The organization. The situation. The timing.
Nobody’s the villain. You just haven’t found the AND yet.
This matters more now than it ever did. The pressure to pick a lane is real.
Being an AND guy isn’t about doing everything at once. It’s about refusing to give up ground you don’t have to give up.
Most of the AND is still there. You just have to go find it.
The Deception of Digital “Be-Better” Frameworks vs. Real-World Counsel
Today I walked into a closet loaded with books, many of which are “be better” books. Good to Great, Atomic Habits, The 7 Habits of Highly Effective People, and plenty more. Whether about becoming a better person or building a better business, that closet is a shrine to self-improvement.
Funny thing though. I haven’t picked up a new one in a long while. And here’s what’s even funnier: I’m probably not any better for it, but my life isn’t any worse either. I think I hit “be better” book overload a few years back. That’s right around when my reading shifted toward fiction and non-political biographies, and I haven’t looked back since.
Don’t get me wrong. I can find plenty of places to improve. I just find myself wanting to discover them through real conversation and lived experience rather than 300 pages of someone else’s framework.
Then I jumped on LinkedIn, and there it was. The same closet, just digital. Getting a be-better book published is hard. Publishing a be-better post takes about four minutes. I’m not saying those posts aren’t helpful, but they carry something books don’t. Books ask you to use your imagination when placing yourself against the ideas on the page. Social media hands you the comparison pre-packaged, scripted, photographed, and filtered for maximum effect.
I’m not swearing off self-improvement content forever. But for me, sometimes the quickest path to feeling bad about myself is reading all the reasons why I should.
Take care.
Blank Calendar Anxiety: Navigating the Post-Exit Freedom Trap
I woke up this morning and looked at my calendar. It was blank. Open. Not a thing on it.
Instead of feeling the day was mine to fully pursue and do as I choose, I felt anxious. Seeing nothing on the calendar had me unsettled. Nothing scheduled to achieve, nothing to accomplish, no plans where I could make a difference.
Most days have something on them. Many days in my past had no open slots at all. But not this day. Just a column of times on the left with nothing to their right but white space.
In that moment, the negative thoughts crept in and for a brief moment I lost myself in that blank calendar.
And then came one of those appreciated long pauses. A calming, reflective pause that led me to ask:
Is the ability to have a blank calendar, without expectations or consequences, one of the greatest achievements of all?
Think about that for a moment. We spend years, often decades, working, striving, and grinding precisely so that one day we might have control over our own time. We chase that freedom like it’s the finish line.
There’s something almost ironic about that. We achieved our way to freedom, and then don’t know what to do with it when it is an open calendar sitting right before our eyes.
Maybe instead of anxiety, that blank calendar deserves something more. Just maybe, it is the proof that time, more than ever, is mine.
The Trophy Paradox: Realigning Executive Worth in Late-Stage Careers
I recently worked with a gentleman who has had a long and successful career. He was praised by the organization for his leadership, client retention skills, and appreciated by those at the firm for his genuine caring nature. But when he looked at himself, he was disappointed with where he was. Why? Years ago, his primary goal was to bring in new clients for his firm and his family. He achieved that in spades over those prior years, but now, in his latter career years, he was beating himself up and feeling discontented because he wasn’t adding as many new clients. He was overlooking all that he is today and focusing only on how his achievements of yesterday were not being achieved today.
Once he truly understood his worth to the firm – his leadership, his mentoring of newer producers, and his vast value to the culture of the firm – he was able to reset what fulfills him today, which is helping others and his firm accomplish great things.
Someone once said, “Yesterday’s trophies don’t win today’s prizes.” That may be true, but trying to repeat those same accomplishments that won those past trophies today might ignore all the greatness that is present in you and be the source of today’s discontent.
If any of this resonates with you, reach me at frank@frankshadid.com
You have a client visit at 9:00. An associate stops by at 10:00. At 10:30 accounting calls with a problem that needs your attention.
Tomorrow, all those calls stop.
Why? You retired.
Years ago, a company I was with got acquired. In the process, some of the people I truly called friends were let go. Most of them were at a point in life — financially and professionally — where they chose to retire rather than land somewhere new.
I kept up with them. And early on I asked what they missed most about work.
The most common answer was the people. That made complete sense.
But one answer surprised me. They missed the problems.
The very thing many of them had been quietly counting down to escape became one of the things they missed most. Not the politics. Not the pressure. But the problems — the real ones, the ones that required them to think, to decide, to act.
It took me a while to understand why.
Problems are what made the phone ring. Problems were why you were in the room. Problems were the reason a client called at 9:00, an associate stopped by at 10:00, and accounting needed you at 10:30.
You weren’t just a title. You were someone worth calling because you could actually help.
And when the role ends, that stops too. Not gradually. Pretty much all at once.
Most men spend years preparing financially for retirement or a major transition. Very few prepare for the morning the calendar goes quiet and nobody needs anything from them.
I’m not sure what problems are sitting on your desk today. But it might be worth imagining, just for a moment, a life without them.
A break sounds good. A permanent absence of them is something else entirely.
The network you’ve built over a career isn’t just relationships. It’s a world that runs on problems — yours and theirs. When the role changes, so does your place in it. And most men don’t see it coming until they’re already standing outside it.
That’s worth thinking about before the calls stop. Not after.