Pick a Horse, Please

Do you sometimes have trouble making decisions? Well, then you have come to the right column.  

Pick a horse pleaseYou see, one of the recurring issues that comes up when I am working with someone is when and how to resolve to move in a direction. You’ve got those who rely very purely on gut and will allow that to be the determining factor, often with great speed, and sometimes recklessness. That’s not how I do things, so in conversation I will impress upon them a need for a bit of caution and fact gathering. Developing key questions to help add some external sources to inform a process.

On the other side we have the perfect information crowd, where I find myself squarely placed, who require certainty. Alas, having perfect information isn’t possible. So, I will go through the process of setting up goals related to making the most informed decision.  

Whether speaking to others about their struggle to make a career change or to start-up a new project the same problems arise. One is finding the right advisor which people mention all the time. I shared some information about WHO you turn to for decisions in this recent article.  

The other that is rarely named, but often emerges is that they have heard such varied opinions because they are in an almost endless loop of information gathering which makes actual progress impossible. Remember, you are holding these conversations because of the value of the conversations themselves, but rather because you want to make a decision that is grounded in accumulated knowledge. Much like owning 149 flyswatters or decorative ice trays you may need to pick the one that is best for you and move on. This is exactly where I will bring in the folksy wisdom that they need to pick a horse. 

I know that use of that phrase must evoke in you, reader, a kind of rustic throwback manliness that you’ve come to assume from me and isn't too far off from being true. Ok, maybe it is very, very far. I have ridden a horse outside of a merry-go-round and it wasn’t my favorite experience. I do, though love the idiom as in select a person who you’ve decided to be a primary advice giver on a topic

You see it used often in sports or politics as in someone backed the right or wrong horse aka, they picked the winner or loser in the game or election.  

Where we stumble is in conflating the conversations as the end goal. The decision and the long-term advisor(s) we return to may well be the end. However, for many people the person we listen to is the last person we spoke to. It is like we lack a long/medium-term memory so that the most recent conversation is always the way to go, Until the next conversation takes place….and there is always a next conversation.  

When do I see this coming up the most? Good question. You are my favorite reader because you ask such great questions. A few examples:

  • Someone who gets feedback on the resume or deck over. and over. and over. tweaking in big and small ways based on what are often personal preferences of the last person they engaged.
  • Someone reaching out to figure the best way to accelerate their growth in a field or role holding a multitude of conversations about approaches. Getting differing advice and thinking each time that the last thing they heard must be right. 
  • Someone seeking investment from wealthy investors each of whom shared the secret spice to their success. Furthermore, hearing a ton of ‘improvements’ that should be on the Minimum Viable Product (MVP). So, they keep adding and lose Minimum.

The intention of none of these individuals is bad. However, they have found a way to completely lose all momentum. Sometimes this is because we fear deciding. Once we do, we are open to criticism. However, lacking a decision means you can’t try, test and learn - perhaps fail, but ultimately you can’t succeed if you never launch.

Which brings us back again to horse picking. In life and work we will need to choose that very small set of people that we decide are the ones who will be the experts that we rely on for things. I believe that you probably already have these in other areas of your life, for example where to eat good X food or what entertainment to consume. You know people who you respect and you have decided that these are the people you turn to for those specific things. 


I can tell you that in my life I have the people I turn to for issues as varied as the best new board game, British television, best BBQ or overcoming self-doubt. Similarly, in the professional world I’ve folks that I rely on who are experts on lean start-up, digital strategy or public speaking. (Oh, and many of these experts are significantly younger than me) And I also have the people who I reach out to first when I don’t have an ideal connection who are great at that.

You owe it to yourself to choose those people who you will turn to so you can stop talking and get to realizing the life and work that will make you fulfilled.

Russ Finkelstein is the opposite of your High School Guidance Counselor.  A career coach, social entrepreneur and advisor to founders, he is currently the Director of Coaching with the Roddenberry Fellowship, Coach-in-Residence with StartingBloc Fellowship and a Co-Founder of Title8 a Legal Marketplace. He was a founder of the noted careers website Idealist.org and his new book, "Let's Sort Out Your Career Mess, Together..." is forthcoming in 2021. 

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