Skin in the Game: Why Great Salespeople Don’t Always Make Great Sales Managers & The Checklist for Optimal Mental Health

Intro

Welcome to my weekly newsletter, Iterations, where I discuss random thoughts, ideas, and stuff from my trials and errors that might hopefully be useful to one or two others.

Quote of the Week

“The most important moments of my life have been those in which I felt that my work led to the creation of something unexpected.”– Fernando Botero

With my daughter off school for Carnival yesterday here in Barcelona. My weekly newsletter was delayed by a day. Very much worth it though! She is a six-year-old sensitive creative soul so where better to take her on a day trip, than to the temporary Fernando Botero exhibit here in Barcelona?

Here′s to achieving the unexpected in our work!

Some photos from the exhibit at the Palau Martorell in Barcelona are below.

Behind the Scenes (Projects and Thoughts)

This week’s focus is more of a personal project as I’ve been feeling stagnancy in key areas of my life.

A friend of mine recommended the Landmark program (an American self-help course). I have some reservations about it, so instead I tried a DIY version, whereby I ran a Landmark-inspired session through GPT. With a meeting room at my co-work space booked, I got into some of the guided introspective questions, such as:

• What are the recurring patterns or roadblocks you see in your business, relationships, or mindset?
• What would a major transformation look like for you?
• Where do you currently feel powerless, and how can you take full responsibility for that area?
• The Story vs. The Facts: Write down a situation where you feel blocked. Then separate the raw facts from the story you’ve built around it.
• What would happen if you assumed that everything in your life is happening “because of you” rather than “to you”?
• What’s the boldest, most exciting version of your future?
• What are the biggest actions that would move you toward that future today?
• Write down three times you experienced a difficulty in your life and how you overcame it.

I know a lot of this can feel cheesy, but we probably don’t ask ourselves enough questions, and even less often do we take time to think and write down the answers. I got a lot out of this 1-2 hour exercise:

• Thoughts out of my brain and down onto paper, to form the basis of a plan, as well as being cathartic
• Challenging my thought processes
• A confidence workout (Particulaly from the Write down three times you experienced a difficulty in your life and how you overcame it question)

After finishing the exercises I created some daily tasks and goals with deadlines in an Excel sheet, which I aim to refer to a couple of times a week to keep myself moving forward.

What I’m Experimenting With

Checklists. Pilots do not fly planes without them; surgeons do not perform surgery without them either. So why do we coast through our lives so often without them?

If you haven’t read Checklist Manifesto by Atul Gawande, then I highly suggest you do.

Charlie Munger on Checklists:

“No pilot takes off without going through his checklist: A, B, C, D.... And no bridge player who needs two extra tricks plays a hand without going down his checklist and figuring out how to do it. But these psychology professors think they are so smart that they don’t need a checklist. But they are not that smart. Almost nobody is. Or, maybe, nobody is. And without a checklist, you will screw up time after time, too.”

– Charlie Munger, Worldly Wisdom

I have created a whole bunch of checklists in my life, such as a list before starting to work, one on wrapping work up, what to take to the gym with me, and one for leaving the house (my short-term memory is of the most fallible kind).

I want to highlight just one though, my Mental Health Checklist.

Sometimes you think you are depressed; sometimes though you have probably just forgotten to make your bed, take your vitamins or neglected something else important.

Ask any entrepreneur, and they will tell you mental health can be very temperamental. I am no exception. Not being able to escape a prostrated position in a darkened room one day, I figured it was about time I wrote down the most basic, minimum must-dos I need to tick off every day to keep my mental health in check.

If I do all those things and I still feel down, well then that is probably worth further concern. Most of the time though, I realise I skipped something from my checklist.

Here are my 5 daily mental health non-negotiables. I use ToDoist for this.

1) Making the bed (as per the book Make Your Bed by William H. McRaven whose premise is that if you do this one small task, then you are more likely to complete other tasks.)

2) Exercise (self-explanatory, preventative, and endorphin-inducing). I prefer the morning, as it sets me up mentally for the day.

3) Getting out of the house (I needed to set this one for myself because, on my lowest days, I simply would not leave the house).

4) Talk to someone (sometimes a deep conversation about how you are feeling; other times, just those small interactions. Talking about stuff is a real lifesaver).

5) Morning Journal (especially the gratitude journal. There is normally always something you can be grateful for, even on the darkest of days).

I think the key to this particular list is to keep it as short as possible. Check-in with it every day, and use it as a barometer to empirically measure where your mental health is at.

Podcast/Video Recommendation

Being honest for a second, I’ve been watching far too many motorcycle-related YouTube videos this week. Reviews of various kinds of bikes.

I will spare you from watching those and instead recommend one of my favourite podcasts:

Hamlet Was Wrong - Malcolm Gladwell (Revisionist History)

The podcast discusses:

• Hiring practices and highlighting some potential inefficiencies.
• The Peter Principle, a theory which suggests that people get promoted based on their performance in their current role, rather than their ability to succeed in the new role.

For example, salespeople get promoted to sales managers based on smashing targets, but with management requiring a completely different skill set that doesn’t always work out.

Surprisingly, this is still not widely understood enough by most companies.

Well worth a listen in my opinion, and I’ve used this nihilistic hiring style in BRUK a couple of times last year.

Book of the Week / What I Am Reading

Skin in the Game by Nassim Nicholas Taleb

Having thoroughly enjoyed his earlier book, Black Swan. When I saw the title of this one, I knew I had to read it. Even though it′s book five in his Incerto series, I thought I would skip straight ahead to it and come back to the others later.

In recent years I have worked with far too many people without skin in the game. Also in a conversation recently with business lawyer Richard Edo Gómez regarding the current state of the Spanish venture capital market (likely relevant outside of Spain too), he mentioned to me that investors these days rarely invest in businesses where the founding team has no skin in the game (i.e., putting their own money in). So this is a subject close to my heart and one I wanted to go much deeper on.

To summarise this book in one sentence it′s a series of arguments to support a case that those who make decisions should also be exposed to their consequences.

I.e., politicians who make decisions but are exempt from the consequences.

Bankers who invest other people’s money only to be bailed out when those investments go south.

Having experienced first-hand with BRUK what it is like to have skin in the game, both on the up and downside, I know that being well-versed with the theories in this book and putting them into practice will help me in my decision-making going forward in my business career.

Where do you need to have skin in the game in your life? What checklists might you build to take care of your mental health? I’d love to hear your thoughts. Send me a direct message or comment if you want to add your say on any of those topics.

Have an incredible week ahead. Keep iterating, keep trying, and keep learning!

Yours faithfully,

Matthew Barton