News and Insights

Do The Painful Thing First

I’ve never actually kicked a can down the road, and I don’t think I’ve seen someone do it. Perhaps it’s a result of being a Millennial, maybe the generation before me would just kick cans around. I don’t know. I grew up on AIM chats and burning CDs and trying not to walk too fast so my Discman wouldn’t skip (the 20 somethings at our firm reading this right now, are putting down their TikTok videos and Google searching “Discman”).

It’s my opinion that regardless of your generation, or the number of cans you’ve physically kicked, the act of delaying something hard is a common past time for many…myself included.

Why are we wired this way? Granted, some of us are better than others. Some people, perhaps due to scar tissue from a bad experience delaying a decision that haunts them, over index and make all decisions equally painful and equally rushed.

I don’t have an RKCA branded matrix or kit to share in this monthly RKCA Insight post. And I also fully recognize that these monthly emails have turned more into strategies and examples and less on the mechanics of a deal. We’re doing this intentionally, recognizing that the mechanics of a transaction have been well documented. Our strength as a firm lies, by way of our history and our shared model of both sell-side advisory and our direct investment practice,  in our experience to know what pitfalls may exist that blow up a transaction. What I can tell you, from direct experience and from our learnings over decades with business owners, is that those painful things you’re not doing, are what you think about before bed each night.

If you’ve had the experience of consistent nights (2+ nights in my opinion)  where you are going to bed thinking about “I STILL need to terminate that employee and wish I had today” or “I STILL need to let that customer go because they’re not profitable but maybe next month,” then you are delaying painful decisions and need an intervention. Two nights turn to two weeks and all of a sudden that employee you wanted to terminate in 2020 is still coming into the office late in 2022.

At the same time, we can rationalize pretty much any decision. And, if you’re a business owner, there are no shortage of other items to put on your checklist ahead of that painful thing you need to do first. Often, the moments of your day sidetrack you and you genuinely cannot get to that painful thing. Those nights are less restless. But when the sticky note reminder, or calendar pop up hits you and you ignore it, you’re only delaying the inevitable. Whether fixating on a problem, hiding it, or dribbling out a partial solution while you wait for something (markets to shift, customers to return) – all these things almost always, in my opinion, compound a negative situation further.

In his 2002 book “Who Says Elephants Can’t Dance?”, Louis Gerstner, the former IBM CEO talked about this:

“I’ve had a lot of experience turning around troubled companies, and one of the first things I learned was that whatever hard or painful things you have to do, do them quickly and make sure everyone knows what you are doing and why.” 1

Facing the music, picking the can up instead of kicking it, whatever the analogy here that helps, do it. Some considerations:

  • Is there something you’re avoiding right now because it’s painful?
  • If you have to do it regardless, and you’re suffering from not doing it, you’re suffering 2x what you should
  • Who in your organization do you need to explain this decision to so that no one is in doubt as to why you are doing it?

Why is this so important? And why is an investment bank talking about making painful decisions first? Often, in the businesses we are engaging with, we are not just serving as advisors or investors but as therapists, shock absorbers, and consensus builders. We’re also painstakingly examining your business because a buyer is going to do the exact same thing and we want you ready. And what happens in any detailed analysis of your business as you’re getting ready to sell? Those painful things you’ve been avoiding come to light. The “I need to buy my brother out before we sell but I don’t want to mess up Thanksgiving, so I’ll hold off” finally comes to light when you’re ready to sell for X and your brother (who has yet been bought out) wants to sell for Y.

So what do you do if you don’t have that muscle to face the painful things in your business? Simply, the “Painful Thing First Diet.” In my opinion, advancing your ability to face these painful things is a little bit like dieting. It’s not something that you read once, commit to do, do it once, and then you get to fix it. It’s something that you must fight with every day. There are conflicts of interest. There are service providers. There are absentee owners. There are employees and customers. There are your own behaviors. What you need is heightened awareness and vigilance. Therefore, what is one painful thing you’ll get up and “eat” every morning.

We also need to realize we’re not going to solve it on our own. This is where bankers, Boards, spouses, wealth advisors, and others come in and say “hey you haven’t turned over that rock, I know you’re anxious about what’s underneath it, but you need to turn it over and see what it is…stop kicking that can around.”

1. “Who Says Elephants Can’t Dance” Louis Gerstner, 2002.


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