Perfect Day Upstartist Diaries

Evaluating Your Perfect Day

Did today matter? Why or why not?

Living your perfect day tests what matters to you. We must measure our experiments to draw conclusions.

Nothing gives me more insight on what really matters than daily reflection.

It hasn’t been easy. Looking in the mirror and admitting that you spent no time doing what you say is most important to you is sobering. And I’m usually exhausted at day’s end. So I’ve gone days and even weeks avoiding this daily audit. 

That’s why my core principles for daily reflection are:

  1. It should take the least effort possible. Owning up to our goals and values is already tough. The less questions and the easier to complete, the better.
  1. Data captured should have a strong signal-to-noise ratio; it should be easy to review your week and get insight about your perfect day
  1. The daily review should remind you of what’s most important, and be a compass for whether you’re heading the right direction.

Below I share seven ways you can look back on your day. I hope they help you design your own daily audit. 

Evaluate Each Day with One Basic Question

Did today matter?

Why or why not?

Doing this enough times unearths what makes your day feel worthwhile or worthless. The answers may surprise you.

Evaluate Each Day with One Quote, Word, or Theme

At different times in my life, a quote or theme has guided and inspired me.

One year the theme was “momentum.” This meant building the skills, network, and habits that would create inevitable momentum towards my financial goals. Keeping “momentum” front and center moved me to action when I was lazy, distracted, or lost. 

This year the theme is “gift.” To me, this means living in gratitude and in a world of abundance, where it’s only natural to give; not thinking how little I have, but how much I have. It means receiving and sharing gifts in a world where relationships, leisure and nature are not commoditized. I also want to help others give their greatest gifts, the reason why I’m writing about the perfect day. 

Or maybe a quote is your north star.

My favorite quote about living a perfect day is from Kalidasa, the fifth century Sanskrit poet:

Yesterday is but a dream, and tomorrow
is only a vision. But today well lived makes
every yesterday a dream of happiness, and
every tomorrow a vision of hope.


When it’s over, will this day bring me happiness each time I think about it? And lived well, does it give me hope for the future? I think this quote beautifully captures the balance between living in the present and living for the future.

Each night before bed, what quote, word, or theme frames how you reflect on your day? Did you live up to it?

Daily Score, Activities and Indicator (Jim Collins)

Jim Collins, the best selling author of Good to Great, recently discussed his daily evaluation on The Tim Ferriss Show.

His priority is creative work. He therefore maintains a minimum of 1,000 creative work hours over the past 365 days. He projects where he’ll be in 3-6 months if he keeps his current pace.

He also briefly recounts each day’s activities (i.e. got up early, two hours of great creative work, breakfast with Joanne, five hours creative work, work out, nap, three hours of creative work, enjoyed dinner with Joanne, bed) and scores each day: 

-2 = bad day / super negative
-1 = negative
0 = “meh”
1 = positive
2 = fantastic day / super positive

Then he can look back at the past month and tease out what activities led to fantastic days, and vice versa. Three activities give him the feeling of a fantastic day: increasing simplicity, time in the flow state, and time with loved ones.

Collins’ method was inspired by studying George Dantzig’s Simplex Method as a math science major: 

“If you’re trying to find optimal answer to multi-variant problem where there’s lots and lots of variables… what he showed was under certain conditions, all you have to do is find the local optimum – what’s the best next step? Under certain conditions [the best next step] is mathematically guaranteed to navigate you to the optimal end point.”

So if you keep iterating and adjusting your day based on score, you’ll get to your perfect day. 

I love this method for its simplicity and high signal-to-noise ratio. 

Before learning his method, I used to rank my days from one to five, one being a horrible day and five being an amazing day. Scoring days as negative, neutral or positive makes a lot more sense. 

I’ve also concluded that listing the day’s activities is the best way to find what fulfills you. Sometimes I would check everything off my perfect day list but would still feel incomplete. The combination of activities and score helped me discover that deep work, connection, and exercise are essential to my perfect day. 

Finally, using a leading indicator within your control (i.e. average creative hours) is more motivating than using a lagging indicator outside your control (i.e. writing a best selling book).

What leading indicator – within your control – moves you towards your perfect day now and in the future?

The Daily Questions (Marshall Goldsmith)

Marshall Goldsmith has been recognized by Thinkers50, Fast Company, and INC Magazine as one of the world’s top executive coaches. He’s an expert at behavior change.

After decades of executive coaching and self-experimentation, Goldsmith has come up with six daily questions. Central to his methodology is to ask active questions that encourage engagement. So instead of asking yes/no questions you should preface each question with “Did I do my best to…?”

  1. Did I do my best to… set clear goals?
  2. Did I do my best to… make progress towards goal achievement?
  3. Did I do my best to… find meaning?
  4. Did I do my best to… be happy?
  5. Did I do my best to… build positive relationships?
  6. Did I do my best to… be fully engaged?

You score your effort on a scale of 1-10, and then see your weekly average.

Each question should 1) cover truly important items and 2) help you become the person you want to be.

I started off with 10 daily questions. Some became redundant because they became life habits (eating mostly vegetables) or because they were unrealistic for my work situation (sticking to social media times). Your questions should change over time – otherwise you’re not evolving.

I also found doing 10 things / day to feel burdensome, like making a “to do list” of 10 items and only checking off one item – even if that task made me evaluate the day as fantastic.

Only by auditing your day consistently can you arrive at your ideal daily report. Some of you can handle ten daily questions. But if you’re easily overwhelmed like me, keep simplifying until you arrive at your most important questions.

It is incredibly difficult for any of us to look in the mirror every day and face the reality that we didn’t even try to do what we claimed was most important in our lives.

Marshall Goldsmith, Triggers: Creating Behavior that Lasts

Ladder-Present and Ladder-Future (The Cantril Scale)

Another way to score your day is with two simple questions:

“Imagine a ladder with steps numbered from zero at the bottom to 10 at the top. The top of the ladder represents the best possible life for you and the bottom of the ladder represents the worst possible life for you.

  • On which step of the ladder would you say you personally feel you stand at this time? (ladder-present)
  • On which step do you think you will stand about five years from now? (ladder-future)”

The Cantril Self-Anchoring Striving Scale, developed by social researcher Dr. Hadley Cantril in 1965, has been used by Gallup to assess well being in more than 150 countries.

Based on statistical studies of the ladder-present and ladder-future scale, Gallup formed three distinct groups of well being:

Thriving – well-being that is strong, consistent, and progressing. These respondents have positive views of their present life situation (7+) and have positive views of the next five years (8+). They report significantly fewer health problems, fewer sick days, less worry, stress, sadness, anger, and more happiness, enjoyment, interest, and respect.

Struggling – well-being that is moderate or inconsistent. These respondents have moderate views of their present life situation OR moderate OR negative views of their future. They are either struggling in the present, or expect to struggle in the future. They report more daily stress and worry about money than the “thriving” respondents, and more than double the amount of sick days. They are more likely to smoke, and are less likely to eat healthy.

Suffering – well-being that is at high risk. These respondents have poor ratings of their current life situation (4 and below) AND negative views of the next five years (4 and below). They are more likely to report lacking the basics of food and shelter, more likely to have physical pain, a lot of stress, worry, sadness, and anger. They have less access to health insurance and care, and more than double the disease burden, in comparison to “thriving” respondents.”

Combine these two questions with a daily activity recap to learn what makes you thrive. What makes you feel you’re living your best possible life? What makes you optimistic about the future?

Feeling safe, financially secure, healthy and having strong relationships are what make me rank my present day and future days 7+ on a 10 point scale.

What gives you a feeling of well-being that is strong, consistent and progressing?

The Book (Geshe Michael Roach)

Michael Roach became the first American to complete and receive the “Geshe” degree after studying 25 years in a Buddhist Monastery. 

His method is based on a simple idea: daily vigilance.

While intended for Zen Buddhists, you can also use The Book to be your best self on your perfect day.

Let’s say you have 10 core values or 10 adjectives to describe your perfect day.

Here are 10 of mine: focused, exciting, generous, valuable, connected, clean energy, thankful, joyful, peaceful, and magical.

Every three hours, you list one, and reflect upon your actions.

+ : a specific action you did to support your value or state
– : a specific action you did against your value or state
To do: a specific action you will do in next 24-48 hours to support your value or state.

The book for someone following the 10 Buddhist precepts could look like this:

Can’t think of anything? Free associate anything with your value in the recent days or week.

For example, at 8am I write down “generous.” I can write down:

+ : treated Matt’s dad to seafood dinner yesterday
– : why not treat yourself to a good meal this week?
to do : get parting gift for security guard leaving end of month

Then at the end of the day, you write the three best, and three worst things you did that day related to any of your values or states of being. Rejoice in your three positives and examine your three negatives. And note what you realize you need to do.

Geshe Michael keeps his last 50 books to see how his habits – and thinking – change over time.

This clearly requires the most effort of all the daily audits. A less demanding version could be to go through one or two words each day (instead of one word every three hours). Still, I like how The Book method pins you to your most important values.

The DJ Daily

You can see my daily evaluation form here.

It contains words, quotes, and images that speak to me, so I am inspired to come back each day.

I link to the form on Apple’s Notes App so it’s accessible on my iPhone and Macbook. It takes three minutes to complete.

I’ve learned to focus on one new habit change in my DJ Daily, whether that’s a daily meditation or random act of kindness. Focusing on one thing is doable; trying to change two or more habits simultaneously is difficult.

What’s your daily reflection method?  

Absorb what is useful
Discard what is not
Add what is uniquely your own.

Bruce Lee

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3 replies on “Evaluating Your Perfect Day”

Wow, I didn’t know living can be optimized in such an elaborate and thoughtful way. Also, you rock as a writer! Thanks for summarizing all these books and podcast. This reminds me of what one of my mentors told me before I decided to study acupuncture…he asked me to simplify my life until there are only 3 things that matter to me and then dedicate every moment of my life to those three. He said it took him 55 years to find those 3 things and that was when he went to school and now have become the best acupuncturist I’ve met. I do appreciate the “outsights” and data-driven approach for more accountability and some form of memory-recording in the DJ daily. You inspired me to think about journaling in a different way (motivation and precious memory keepsake).

Thanks for reading this and I’m glad it helped you in some way. “Dedicate every moment of my life to those three.” What powerful simplicity, and wisdom. I think deep down we know what these are; the challenge is to honor those dreams despite what others or society says. Which reminds me of the number one regret of the dying (according to Australian nurse Bronnie Ware): “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Yes, listen and obey the heart. 🙂 Really enjoy reading your posts. Hope I can write something this inspiring and helpful in the future!

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