Three Questions to Ask Yourself Every Day

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I subscribe to a newsletter from marketer Max Bernstein that unfortunately seems to be in hibernation. The most recent issue (which was back in March) featured three questions that he has written down on a small whiteboard so he sees them each and every day.

These questions and their very brief descriptions are good enough that I have to share them with you.

(For the record, I just spent a while trying to find him sharing these three questions anywhere online that is linkable so I could send you straight to it but I can’t find it anywhere other than the email. And there’s not even a web-based version of the email to link to! So that’s why I haven’t linked directly to him sharing these questions - I literally don’t think it exists anywhere online!)

So here are the three questions from Max Bernstein with my thoughts on each:

Who Am I Helping Today?

Zig Ziglar famously said, "You can have everything in life you want, if you will just help other people get what they want."

When I start focusing on who I can help today and actively seek solutions to their problems, all my fears, frustrations, and mental blocks fade away.

This question is vital and its answer should fuel everything we do professionally. I use a similar question in my personal life which is “who needs me on my A-game today?”

What Is The Golden Nugget?

I could fill up an entire spreadsheet with content from tweets, calls, courses, articles, and videos that I come in contact with before noon. Instead of worrying about remembering everything, I focus on "what is one thing I can take away from each thing I consume."

​What a great way to deal with the overwhelming nature of the always-connected world we live in: Look for the one overarching takeaway from everything you encounter.

And he encourages you to write it down in a notebook. Simple and powerful.

Am I Acting With Urgency?

Complacency is the easiest trap to fall into when you don't have anyone looking over your shoulder.

Working with a sense of urgency puts me in motion.

It creates connections.

It advances projects.

It gets stuff done.

And when all those things happen, it is a lot of fun.

The single most difficult thing for me as an entrepreneurial musician is maintaining urgency when it’s just me working on something. I’m great at urgency when I have an external deadline. But so many things in my portfolio career have internal deadlines - meaning there won’t be another person I have to email to say “I’ve let you down” if I blow past it.

I have a feeling that regularly asking myself this question, like Max suggests, is going to help me keep a sense of urgency which will pay huge dividends for me moving forward.

Everything Must Be Paid for Twice

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I stumbled onto this blog post and it has my head spinning! Here’s an excerpt:

“If you look around your home, you might notice many possessions for which you’ve paid the first price but not the second. Unused memberships, unread books, unplayed games, unknitted yarns.”

The author points out that there’s a first price (which is usually money) to acquire things like books or a budgeting app but that a second price must be paid in order to actually use the thing, like taking the time to read the book or set up the app.

He argues that the second price is frequently higher than the first price and speaks to the negative effects of accumulating things where we have yet to pay the second price:

But no matter how many cool things you acquire, you don’t gain any more time or energy with which to pay their second prices—to use the gym membership, to read the unabridged classics, to make the ukulele sound good — and so their rewards remain unredeemed.

I believe this is one reason our modern lifestyles can feel a little self-defeating sometimes. In our search for fulfillment, we keep paying first prices, creating a correspondingly enormous debt of unpaid second prices. Yet the rewards of any purchase – the reason we buy it at all — stay locked up until both prices are paid.

How does this specifically relate to my own journey as an entrepreneurial musician with a portfolio career?

I am a firm believer in online courses. The best of them offer instant, in-depth access to the world’s foremost experts on just about anything. We have never lived in a better time to learn, really learn, from the best in the world.

But there is a problem with online courses.

There’s always another one!

I have purchased a number of online courses that I haven’t even begun. And purchasing yet another course, no matter how great the sale is or how relevant the material is to my journey, isn’t helping me dig out of that hole.

So in 2022 I made a rule that I am no longer purchasing any online courses until I actually complete some of them. It’s not like I’m sitting on a dozen of them but the number also isn’t two! And with each passing purchase I felt a little more overwhelmed by all of these uncompleted (and sometimes unstarted - which I just made a word) courses. So I’ve hit timeout.

I also bought a subscription to QuickBooks last year to get organized with my finances so that tax time wasn’t so chaotic.

But it turns out that second price of that purchase was a lot bigger than I thought it would be. I not only had to set it up but I then had to keep inputting data over and over and over again.

You might be sitting there wondering “well how the hell did you think it was going to work?” and you would be right to ask that. I just underestimated how much work it would be to stay on top of the data input.

I don’t regret the decision and don’t consider the subscription wasted money. I needed to experience it before I realized that two days of chaos at tax time was a lower second price for me than updating the app every week (meaning 50+ times a year.)

I would recommend the four minutes it will take to read the full blog post. It made me more thoughtful about acquiring things and encouraged me to use the things I already have - both good things!

I’ll leave you with two questions to ask yourself:

What things have you acquired where you have yet to pay the second price? And for each, should you pay that second price now, get rid of it, or stay the course?

A 15-Minute Exercise to Expose Where You Are 'Playing Small'

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I stumbled onto this idea via Sahil Bloom’s newsletter (which often covers not exactly what I need to move my portfolio career forward but then every once in a while it’s a home run.) This is a really, really good idea to get some clarity about where you might be “playing small.”

Sit down with a small group of friends or trusted intellectual sparring partners. Speak for 10-15 minutes on your business and focus areas.

Then work to ask and answer a few key questions:

  • Where are you playing small that you could be playing much, much bigger?

  • What is holding you back from playing that bigger game?

  • Is it real or imagined?

If you go through this exercise, I guarantee you'll uncover a few areas where you could be thinking bigger. Try it and let me know what you learn.

I am setting this up for myself next week and will circle back if it is as useful as I think it is going to be!