You Don’t Know What You Don’t Know

My parents are in the middle of winding down their farm operation in Northern Iowa. The idea was simple: sell the land; retire and walk off into the sunset. But as they began the process, so too came layers of complication. The deal involved land that had been in the family for decades, the estate of my grandmother, multiple siblings (nine total, to be exact), and complex tax treatment. It was to say the least – complicated.  

At some point in the process, they realized they needed help—not because they lacked capability, but because there’s no clear-cut blueprint for navigating situations like this. You can only go so far on your own before the complexity outpaces what you can manage without professional help.

The decision, to pause, step back, and bring in people who knew what they were doing was necessary but at the same time, not easy to do. However, it made everything better. Lawyers, accountants, retirement planning, real estate professionals, it was a real mix. And the outcome was smoother and more strategic because they didn’t try to carry it alone.

Watching this unfold, it hit me that this is the same inflection point every entrepreneur reaches at some stage. You build something. You grow it. You operate in the trenches. But eventually, the problems outpace the playbook. And you either dig in deeper (often to your own detriment), or you raise your hand and say, “Okay, who can help?”

Reaching out for help is not a weakness, it is strategy.

Sometimes the real challenge is the blind spots—the things you don’t know you don’t know. I’ve seen founders get tripped up trying to navigate exits, equity splits, tax planning, or restructuring on their own. Not because they were careless, but because they waited too long to ask for help. And I get it—asking for help can feel expensive and vulnerable. But ignoring complexity doesn’t make it go away. If anything, it compounds it.

That’s been my biggest takeaway through all of this: whether you’re stepping away from a family business or scaling something new, there’s real value in having the right people in your corner early. No one builds—or exits—alone.

Sometimes the smartest move isn’t a DIY fix. It’s recognizing the moment you’re in and surrounding yourself with people who know how to guide you through it.