Why you need a business bucket list

Everybody likes to talk about their bucket list, but the truth is most people have little more than a few vague ideas about the things they’d like to do before they die. Sadly, without full commitment to detailing and executing bucket lists, unfulfilled dreams are the most likely outcome.

To avoid that fate, my family—including my two teenage daughters—has taken to not only documenting bucket lists, but also conducting an annual bucket-list review between Christmas and New Year’s Eve each year. Over the course of holiday week dinners, we go around the table each night explaining a few intimate ideas from our lists, reporting on the progress we made in the past year and outlining how we plan to advance toward our goals in the coming year. We encourage each other, hold each other accountable, and collaborate to help one another find ways to achieve our grandest ambitions. For our family, bucket lists are very real and a scheduled tradition.

Creating a business bucket list

Around the time of our most recent bucket-list session, I started thinking about how that process could work for business leaders. I’ve come to believe that every executive should have a business bucket list – a catalog of bold, risky, possibly outrageous ideas that you’d pursue if you were unencumbered by resource constraints, shareholder demands or internal politics.

I’m not talking about your business plan or even your stretch goals. Remember, most business plans are things you’re actually going to do in a defined time period. Some business plans include stretch goals, but those are just extensions of the underlying plan. They’ve passed through a committee, been allocated a slimmed-down budget and inevitably watered down by the organization’s risk tolerance and internal political sensitivity.

Your business bucket list should include one or two items that would scare the bejesus out of some of the people who sign off on your annual business plans. For instance, what if you oversee a division that you believe would be more successful on its own or in somebody else’s hands? Even if this division generates more than half your revenue, is run by a son of the founder and is considered an untouchable core asset, put this idea on your bucket list. It may be too early to talk about it with others, but if the idea of divesting this unit has occurred to you it’s probably flickered in others’ minds as well. After putting it on your list you can start broaching it with some trusted lieutenants or peers and discreetly investigating possible paths to achieve the vision. The idea here is that you’ll play it safe your entire career if you don’t ever bring some of your crazy ideas to fruition.

To avoid erratically tackling the crazy ideas on your business bucket list, it’s critical to approach it in a methodical manner, just like my family has with our personal bucket lists. Some guidelines:

• Mull it over yourself first. At first blush, bucket list ideas are disruptive, audacious or downright blasphemous. You can’t attempt them without first studying the possibilities and risks and thinking carefully about the resources required, the people impacted and the steps you’ll have to take. There will be a time to reveal your “if I were King for a day” ideas, but in most cases they should remain confidential until you’ve identified a potential road to actually making it happen.

• Overcome the fear of offending people. Most bucket list items are going to rub somebody the wrong way. Maybe it’s investing heavily in a new product that would cannibalize an existing line, which is bound to sow angst among the existing team. But in the long run, if you can convince the team that your idea is the best way forward, they’ll get behind it. Don’t let their first reaction – or in the case of a provocative bucket-list idea, their fourth or fifth – deter you.

• Get people bought into your idea. Once you have clarity on your bucket list items and a few initial thoughts on how to achieve them, start quietly building support. Collect data and privately show it to the people you trust and whose support you’ll need. Distribute information that supports your position; socialize people to the concept. Eventually enough people who together can make things happen will say “Here’s a great idea,” and you’ll just chuckle, head back to your office and check off an item on your bucket list.

A bucket list to a business case

To be clear, a business bucket list isn’t an excuse for taking reckless chances, especially with other people’s money, or for subverting your board of directors. Boards serve an important purpose in keeping companies out of the ditch. But a director’s role is to convince leaders and allocate the resources to accomplish things that are within the realm of possibility. And when you do, you will enjoy a more fulfilling—and impactful—career.

The bucket list is where you test out ideas that most would reject at first, and rightly so, but will come to accept after you’ve built your case. By methodically working toward the ultimate goal of checking an item off your list, you can develop your idea to the point where others see the value and, eventually, endorse the pursuit.

That’s what happens with our personal bucket lists. My wife had three outrageous bucket list items: To see Kenny Chesney play in a small venue, to catch a glimpse of him on his yacht and to set foot on an exclusive Caribbean island owned by a certain billionaire.

After hearing her describe those dreams in our annual family bucket-list review, I kept them in the back of my mind and suddenly last year I came across a golden opportunity to see Chesney play on the aforementioned island before an intimate group of 250 fans. We flew down and rented a boat. As luck would have it, there was Chesney hanging out on the boat in front of us checking in at customs. Picture of Kenny on his boat? Check. We went ashore on the island (check) and went on to standing just 10 feet away from the band as they delighted us revelers (check) – a trifecta bucket-list combo!

Was the timing right? No. Was the money right? God no. But we managed to check three items off her bucket list in one outrageous trip. Audacious goal executed. On to next year.  

My wife had three outrageous bucket list items: To see Kenny Chesney play in a small venue, to catch a glimpse of him on his yacht and to set foot on an exclusive Caribbean island owned by a certain billionaire. We made it happen!