Perfect Day Upstartist Diaries

Making Your Perfect Day a Reality

Design a day full of small wins, and your perfect day is right around the corner. Here are eight exercises to help you do so.

How can you live more of your perfect day, every day?

Below are eight exercises to help you make the transition. Our willpower is limited, so we have to make living our perfect day as simple and easy as possible. Then we can build the momentum to make even bigger changes.

1. One Hour
2. Find People Living Your Perfect Day
3. Design Around Constraints
4. The Wheel of Change
5. Identify Your Triggers
6. The Money Test
7. Prioritize Around Values
8. Hack Motivation with Success Spirals

1. One Hour

As a first step, spend at least an hour today giving your fullest gift, whatever that is for today, so that when you go to sleep at night you know you couldn’t have lived your day with more courage, creativity, and giving. 

David Deida

Simple right?

You’ve spent 10 minutes envisioning your perfect day. Now is the time to act.

Don’t wait. Each wasted moment degrades your clarity of purpose.

Even spending 15 minutes a day towards the actualization of your perfect day is a first step. I recommend doing what you love at least one hour a day.

Did your eyes just glaze over?

One hour? I have family duties. I’m exhausted after work. I don’t have enough time. 

If you don’t or can’t spend 1/24 of the day living your best life, maybe the future you’ve been dreaming about for so long is simply a fantasy. 

This one hour should be thrilling and fulfilling! You need it and the world needs it. We need you to be burning bright, not passing days half dim.

When you commit, new paths forward appear.

Even if you realize your vision is a fantasy, you’ve gained outsight.

Do something, anything, now.

2. Find People Living your Perfect Day (or Parts of It)

The fastest way to change yourself is to hang out with people who are already the way you want to be.

– Reid Hoffman

Attending DC BKK, a conference for location-independent entrepreneurs, was life-changing.

I had tried for months to make money online, but couldn’t breakthrough. I had read countless books and blogs and followed their directions step-by-step. 

Business plan. Done
MVP. Done
Marketing channel traction. Done

Where was the money? 

It had been almost a year since I quit my corporate job. Maybe I just wasn’t cut out to be an entrepreneur. How was I going to explain this gap year to employers?

I couldn’t do this on my own. I needed help. With my back against the wall, I bought a ticket to Bangkok for the conference.  

The advice was helpful. But more transformational was being around 40 other location independent entrepreneurs who were making a great living selling cat furniture, yoga scheduling software and condoms. They weren’t any smarter than me. They had just committed to this path – and stayed in the game long enough – to succeed.

I shared meals with Derek Sivers, who had sold his music business for 22 million dollars. Although the keynote speaker, he was as humble, grounded and eager to learn as newbies like me. It was a drastic change from the rigid status hierarchies of the corporate world. Here was Derek, sitting next to me in a t-shirt and sandals, taking notes as a 20-something talked about selling e-cigarettes in China. This world was not about age, status, or experience – it was about building stuff customers wanted.

After that conference I made my first consulting sale. Yes, I used advice from a speaker and made my offer page more frictionless. But just being with this group for three days changed my reference points for what was possible. I could do this!

Who do you know already living your perfect day? How can you spend more time with them (hint: offer them something of value)? Where and when is the next gathering of people you want to be like? Go. Buy a ticket if you have to. It will change your life.

3. Design Around Constraints

24 hours. That’s all we have each day.

Sleep. Eat. Poop. Move. These are our biological needs.

Peak. Trough. Recovery. This is our daily energy cycle.

Designing your day around your time, body and energy constraints – I call them blocks – is a common-sense way to live your perfect day.

For example, I’ve learned that I need eight hours of sleep per day, and that I get hungry (to the point that I can’t concentrate) every four hours. I have the most focus at the beginning of the day; by nighttime my willpower is depleted. Hence one of my rules: no important decisions after dinner! 

I also need to sweat each day or my energy and sleep suffers. That usually takes one hour. Meals with friends last at least one hour, so I usually need 2-3 hours for meals. After my biological needs of sleep, hunger and exercise are met, I’m left with 12 hours. 

Knowing all this, I’ve set up my perfect day to have two long blocks of creative work in the morning and early afternoon, and one shorter block for routine administrative work in the late afternoon. Which leaves me four hours for socializing, play, and miscellaneous time sucks, like errands and commuting. 

Time Constraints:

  • 12 hours for physiological needs: sleep, eating and exercise
  • 12 hours for everything else

Body Constraints:

  • Need 8 hours for sleep
  • Need 3 hours for eating / body maintenance
  • Need 1 hour for exercise
  • Hunger pangs every 4 hours
  • Max 3 hour blocks of sedentary screen time
  • Need nature every day

Energy Constraints:

  • Peak hours 1-7 awake — schedule favorite, most important work
  • Trough hours 8-9 — schedule mindless stuff here or rest
  • Recovery hours 10-11 — schedule routine, less important work
  • End of day hours 12-16 — schedule fun, zero-willpower activities


12am: sleep block
1am: sleep block
2am: sleep block
3am: sleep block
4am: sleep block
5am: sleep block
6am: sleep block
7am: sleep block
8am: morning rituals + breakfast
9am: creative block #1
10am: creative block #1
11am: creative block #1
12pm: lunch
1pm: creative block #2
2pm: creative block #2
3:30pm: BREAK (nap, errands, exercise)
4:30pm: admin/routine work block
5pm: admin/routine work block
6pm: LOST HOUR (commuting, errands, interruptions, meetups)
7pm: dinner
8pm: fun block (socialize, play, learn, exercise, help)
9pm: fun block
10pm: fun block
11pm: end of day rituals + bedtime
12am: sleep

This schedule is NOT rigid; in fact I often wake up late. The shape of each day changes with events, outside demands, and your body’s needs and moods. Some of you may prefer NO work on your perfect day, or may prefer a manager’s schedule to my maker’s schedule. There is no formula!  Nevertheless knowing your time, body and energy constraints gives you pre-set blocks to design your day, like legos.

Once you know your blocks, you can fill them with multiple perfect day activities i.e. eating meals with friends, exercising in nature, walking (instead of driving) to work, meals and meetings to get one hour of exercise. 

You’ll also have a standard for your off days. If I’m sick and can squeeze in one creative block and one meal with friends, that’s a GREAT day, even if I spend most of it in bed.

This is a sobering exercise. You realize you have limited hours each day to live your best life. Why not maximize this time and do the right things at the right times?

What are your basic sleep, hunger and exercise cycles? When are you the sharpest?

If you were to divide your typical day into blocks, what would they look like? 

Which brings us to the next exercise…

4. The Wheel of Change

When it comes to transforming your current day to your perfect day, you only have four options. 

The Wheel of Change, from Marshall Goldsmith’s book Triggers
  1. Creating: what positive elements do you want to create in the future (from adding to inventing)
  2. Eliminating: what negative elements do you want to eliminate in the future (from reducing to eradicating)
  3. Accepting: what negative elements do you want to accept in the future (from delaying to making peace)
  4. Preserving: what positive elements do you want to keep in the future (from maintaining to improving)

Then within each of the four categories, there’s a continuum of how much you want to keep or change. For example, under creating, you can invent a new activity or you can add to an existing activity. Under eliminating, you can eradicate an activity or merely reduce it, and so forth.

When we think of change, most of us focus on creating new behaviors, activities and identities. But equally important are the other three categories. We must preserve what serves us well, and be disciplined to not abandon these for shiny objects. We are often reluctant to eliminate things we enjoy that aren’t helpful to our purpose. Finally, sometimes we must accept when we are powerless to make a difference.

What one behavior – if created, eliminated, accepted or preserved – would move you to the closest to your perfect day?

5. Identify Your Triggers 

If we do not create and control our environment, our environment controls us

– Marshall Goldsmith

Most of us ascribe our success to willpower. I got straight A’s because I worked like hell. This narrative runs deep in American culture, from business to fitness.

But the older I get, the more I realize the environment’s role in shaping my success.  

Yes, I worked hard in high school and was co-valedictorian. But this was largely because my mother instilled in me strong study habits. My best friends were also high achievers and co-valedictorians. Studying hard seemed normal.

Changing our behavior as adults is hard enough. We have limited willpower and our environment nudges (and sometimes directs!) our behavior everyday. That’s why we must rig our environment with triggers that make living our perfect day easier.

I highly recommend reading Triggers: Creating Behavior that Lasts, written by world-renowned executive coach Marshall Goldsmith, to learn more. Important for our discussion is to know that our behavioral triggers can be mapped over two dimensions: want and need   

Want vs. Need Triggers from Marshall Goldsmith’s Triggers
  1. We Want It and Need It (where we want to be). The carrot.
  2. We Don’t Want It but Need It (where we need rules, accountability and pain to do the right thing). The stick. 
  3. We Want It but Don’t Need It (where we sacrifice goals for short-term gratification). The candy. We should avoid these triggers, and forgive ourselves for an occasional treat.
  4. We Don’t Need or Want It  (where we don’t want to be). The shit. We should eliminate these triggers, yet also accept that shit is sometimes unavoidable.

To identify your triggers, complete the following exercise.

  1. Pick one behavioral goal you’re pursuing on your perfect day 

Spending less time on social media.

  1. List the people and situations that influence your behavior, and chart them on the want vs. need spectrum. If you’re falling short, you’re probably getting too much of what you want, and not enough of what you need. What’s your plan moving forward?

Situation 1: I’m lonely, bored or need a break, so I mindlessly go to social media for a dopamine hit.

Trigger: Candy (want it, don’t need it)

Plan A: Avoid temptation by taking Facebook and Instagram off phone, install Facebook newsfeed blocker on laptop.

Plan B: Limit distraction by setting 30 minute limit for social media on phone

Situation 2: I need to access social media to find information or for work. But then I get sucked in and forget what I came for.

Trigger: Stick (need it, don’t want it)

Plan A: Open and close a browser tab for each social media task

Plan B: Batch longer social media tasks, during the day and week

Situation 3: Endless texts and alerts from acquaintances who expect me to reply asap. A few are important or from close friends.

Trigger: Stick (need it, don’t want it)

Plan A: Set rules and alerts so important messages come through.

Plan B: Set expectations about timeliness of responses i.e. responding on WhatsApp twice a day.

Plan C: Accept that you can’t make everyone happy; it’s okay to not respond if you’re busy. Just make sure you’re in close contact with people who matter the most.

What counterproductive triggers can you avoid? What productive triggers push you toward your ideal day?

6. The Money Test

If you want a clear picture of your priorities in life, who you are and what you care about, look at your checkbook, your credit-card bills, and bank statement.

– Lynn Twist

We’ve looked at time, but does your money serve your perfect day?

Recently I found myself deliberating over a $180 USD subscription to Masterclass. These teachers were exactly who I wanted to learn from – creative practitioners and masters of their craft, like Malcom Gladwell, Neil Gaman and Judy Blume, who had written countless bestsellers. How did they do it? 

I had agonized over this purchase for eight months (!) but never committed because of the price tag. Finally, a month ago, I sat down and did a quick analysis of how much I had spent on learning this year. 

$70 USD 🙁 🙁 🙁

A Masterclass subscription would bring that up to $250, under 0.5% of my income.

My perfect morning is spent in creative pursuits – writing, hosting, and filmmaking – and I was unwilling to invest 0.5% of my income to learn from some of the world’s greatest writers and filmmakers?

Ridiculous. I’m literally hitting myself myself right now for not acting right away. 

$180 seems like a lot of money with so many free books, podcasts and videos available. But when put into the context of my perfect day, it’s nothing. In fact, it’s the best investment I’ve made this year.

What values does your spending express? Does money flow to your highest values and commitments?

7. Prioritize Your Day around Your Values

The biggest first world problem is comparison syndrome. We see other people doing things and we think, “Look at them. They have more success than us. They must be doing something that’s working.” So we think the grass is greener on the other side and we chase these shiny objects, and when we do that, it actually brings a lot of stress into our lives because we’re doing what other people value and it takes us away from our values.

– Craig Ballantyne

When researching about others’ perfect day, I discovered fitness entrepreneur Craig Ballantyne had written The Perfect Day Formula. Of course I had to learn more!

While I disagree that there is a formula for the perfect day, I do like Craig’s idea of designing your day around your values.

His pyramid of values contains 1) family 2) health 3) wealth and 4) experiences.

Then for each of those values you ask, “In 20 years from now what would you regret NOT doing or achieving?”

I’ve modified his template.

First, what is your pyramid of values? 

Second, in one year from now what would you regret NOT doing or achieving?

Your Pyramid of Values + In One Year, What Would You Regret Not Doing?

For example:

  1. Health: establishing a daily meditation habit 
  2. Relationships: meeting potential long-term partners 
  3. Wealth: spending mornings on creative pursuits 
  4. Joy: writing a book that empowers more people to live their best life

Third, schedule activities supporting these values into your morning, afternoon, evening and nighttime. Craig suggests anticipating common obstacles for these time periods, similar to what we did under Identify Your Triggers. 

Morning / Afternoon / Evening / Nighttime Activity:
Evening Obstacle: 
Plan A:
Plan B: 

For example:
Evening Activity: Dinner with girlfriend
Evening Obstacle: Late for dinner
Plan A: Public accountability to leave office at 5:30pm
Plan B: No glass of wine with dinner if dinner starts past 7pm

Designing your day around your values will drive you to make more right decisions each day.

8. Hack Motivation through Success Spirals

Fail once, lose some confidence and motivation, try less, fail again, and repeat until you’ve no hope left. The biggest hack a motivation hacker can perform is to build her confidence to the size of a volcano.

– Nick Winter

My friend Jimmy changed my life with a simple practice: doing a minimum number of pull-ups per day. It doesn’t matter if that’s 2, 10 or 100. Just do it everyday and get a little better.

Two months ago I started with 10 pull-ups. It sucked. My hands hurt and I felt pathetic. But each day I did at least 10. Soon I upped that to 20/day, then 30/day. Now I’m at 60/day.

Yes, I’ve gotten more ripped too!

But the best part is that I now look forward to my time with the bars. Yes it’s painful sometimes. But hitting my daily pull-up quota is an easy win each day. The message I send consciously and subconsciously?  Every day I’m getting a little stronger. 

Over months that momentum of daily discipline makes you feel unstoppable.

Nick Winter wrote a gem called The Motivation Hacker. In it he proposes a formula (MEVID) for motivation which perfectly explains my pull-up success spiral.

Motivation = (Expectancy x Value) / (Impulse x Delay)

I’m using Nick’s definitions below, and then illustrating them with my pull-ups.

Motivation is the fire, energy, excitement which drives you to act, to achieve your goals. 

Expectancy is your confidence of success. When you’re sure you can win (high expectancy), motivation is high. When you think you’ll probably fail even if you try, you won’t try – motivation is low. Ideally you design tasks with High Expectancy – no matter the task, you know in your core that you can learn to do it well, so you look forward to the challenge.

I know I can do the same number of pull-ups as the day before, maybe even a few more.

Value is both how rewarding a task will be when you finish it and how fun it is while you’re doing it. Working on goals that are important to you brings high motivation. Doing boring, pointless things causes low motivation. Ideally you design tasks with High Value – things so fulfilling that whenever you stop and think about it, you can’t help but grin to yourself.

Fitness is big part of my identity. Working out with Jimmy in the park is fun. I also get a psychological boost everyday. And I feel and look stronger.

Impulsiveness can be thought of as distractibility: how likely you are to put a task off and do something more pressing. When you have other things you’d much rather be doing, your Impulsiveness is high, and your motivation low. If there’s nothing else you could be doing right now, then Impulsiveness is low and motivation high. Ideally you design tasks with Low Impulsiveness – at any time, there’s only one clear thing that you want to do, so you have no problems focusing on it.

I need a break from work, sitting and screens anyway, so I might as well exercise in the park. I can listen to my favorite music too. Also, once you see the results, it’s hard to stop. If you don’t do it, your day feels worse.

Delay is how far off the reward seems to be. This is often hard to manipulate directly: rewards are often delayed so far that we hyperbolically discount them into worthlessness. But sometimes you can set yourself up to perceive Delay differently, thus scoring a big motivation win. Ideally you design tasks with Low Delay – you are always so close to achieving one goal or another that you never lack the urge to finish.

Pull-ups take 15 minutes; the physical “high” is immediate.  

By increasing Expectancy or Value, or decreasing Impulsiveness or Delay, you hack motivation. 

When you know you’re going to succeed, motivation abounds, and vice versa. Design your perfect day so it’s easy to succeed. One way to do this is to set input-based goals (write for one hour) rather than output-based goals (write one page). 


  • You want to meditate. Success spiral: meditate for five minutes a day
  • You want to become a designer. Success spiral: design everyday for fifteen minutes 
  • You want to be more friendly online. Success spiral: support one friend/day online

Just Do It

Design a day full of small wins, and your perfect day is right around the corner.

Act now. Spend a small part your day doing what you love, and make it so easy to do so, that it turns into a success spiral. Spend money and time hanging out with people already living your perfect day. And center your day around your values. Easy wins!

Rig your environment so living your perfect day happens by default. What are your time, body and energy blocks? What can be created, eliminated, accepted or preserved from your current day to get to your ideal day? Do your daily situations have productive triggers?

If you read about these tools but change nothing in your day, I’ve failed.

Just. Get. Started.

Once you commit to action, you’ll start building momentum – and confidence – so that living your perfect day is not only possible, but inevitable. 

Then you can move to evaluating and refining your perfect day.

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