March 11

If You Could Retire Today, What Would Your Ideal Day Look Like?

What would you do if you had a blank slate and could design your day any way you choose? What does your ideal day, or for that matter, your ideal life look like? And no, this isn’t a pointless exercise at creating a pie-in-the-sky vision of a world where you have a zillion dollars and no responsibilities. Although, that does sound quite nice.

Life is too short for us to do things we don’t like, obtain things that aren’t useful, or please people that don’t matter. Defining, with intention, what your ideal day would look like (within the constraints of being a functioning member of society) is the first step to actually living out an ideal life. After all, how you live your days is how you live your life.

What am I doing with my life?

I’ve pondered the “ideal day” question a lot, as I’m sure many other people in my age group have as well. Maybe it’s one version of the dreaded mid-life crisis—when we realize half (probably the more energetic half) of our lives are behind us. Suddenly, we’re caught panicking about how to make the rest of our time on earth count.

I call this the what am I doing with my life moment. Many events can bring on this sudden jolt:

  • You hear of a coworker or even a celebrity passing away unexpectedly, and, boom, you’re struck by the realization that life is too short.
  • You get abruptly laid off from a job you thought you’d coast along at for years and are now left wondering what all of that was for.
  • Or, you become an empty nester and realize you’d spent the last couple of decades wondering when to lie down, and now you actually can.

But you don’t have to wait for something dire to happen to start designing your ideal day, or for that matter, your ideal life.

Right at this very moment, when everything feels ho-hum and life seems to be chugging along okay, is the absolute best time to take stock of whether your everyday reality is in sync with your ideal day vision. And if it’s not, it’s best to take corrective action now to get the two in sync. After all, an ounce of prevention is worth a pound of cure.

Before you begin

Before we define the ideal day, let’s acknowledge the elephant in the room: finances.

I’ll bet that a vast majority of people wouldn’t want their ideal day ruined by the idea of needing to work for money. How can anything be ideal if you’re going to have to do something you aren’t too fond of?

No wonder then that the first and probably the most practical question that pops up when I ask someone to define their ideal day is this: “How do I pay for it?”

Yes, we’ve all heard it: life is too short to spend every day doing something you don’t love. But…what about bills?

Financial freedom

Last I checked, good thoughts or great intentions aren’t acceptable as legal tender to pay for electricity. Bills are a reality in all our lives. But we were certainly not born to work, pay bills, and die.

Unless you have access to a magic cash machine that can produce money on-demand or a spinster aunt who left you a prosperous country in her will, getting finances in shape is a reality most of us need to confront. Hopefully sooner rather than later.

Like religion and diets, money is a topic that can make even the most brazen of us squirm. Plus, I’m not a financial planner, and I’m certainly not your financial planner. Which means I’m not here to give you financial or investment advice. That said, there are some basic tenets about money that apply to almost everyone.

For inspiration, we can look at a concept that has recently gained a large following—the FIRE movement.

FIRE Movement

FIRE, an acronym for ‘Financially Independent, Retire Early,’ is a lifestyle choice adopted by many young and sometimes new entrants into the workforce. The proponents of FIRE determine a target savings goal and then work hard, live frugally, and save aggressively (anywhere between 50 to 70% of their income) for a few years until they reach their “number.”  Once that’s accomplished, they consider themselves “financially independent,” which means they are free to retire from paid employment to pursue their dreams.

Unlike the conventional model of retiring in the mid-to-late 60s, FIRE enthusiasts retire much younger, some even in their 20s. This, in turn, allows them a longer duration to pursue their interests.

As with any concept, there are variations in how people play the FIRE game. Lean-FIRE involves living quite frugally with a smaller nest egg, while Fat-FIRE can mean you’ve saved up enough to live out the rest of your life luxuriously while still not needing to work for a living.

I’m not advocating for anyone to join the FIRE movement (unless you find the concept appealing.) What I’d like to point out are some key lessons we can take away from the FIRE community.

FI lessons

Here are three simple FI lessons for you to understand, watch out for, and act on.

1. Understand this

Chasing money purely for the sake of having more money is an exercise in futility. Money is a means to an end, not the end itself. The sooner we can get this into our heads, the better positioned we’ll be to find happiness.

2. Beware of this

Hedonic adaptation is the phenomenon used to describe how we tend to return to our baseline level of happiness regardless of the stuff we buy. In other words, an expensive new car may make us happy for a few days, but it’s only a matter of time before we get used to the car. Subsequently, our happiness spike levels off to where it was before.

Here’s why it’s essential to be aware of hedonic adaptation: working longer and harder to pay for things such as a larger house or a shinier car won’t really move the happiness needle in the long run. Instead, spending time doing what you love can be much more rewarding.

3. Do this

Define your financial independence (FI) number: the amount of money saved or invested that will let you sleep peacefully at night. Plenty of online calculators can help you uncover this number for yourself based on your lifestyle and risk tolerance.

The FI number is an entirely subjective, judgment-free, and deeply personal number. It could be $1million, $10 million, or $100+ million (for those who can only travel in their private jets and vacation in yachts on their owned islands).

If money is a constraint in getting to your ideal day, the above exercise will help you immensely. The sooner you start financial planning and getting to your FI number, the greater your chances of living not just your ideal day but your ideal life.

Ideal day—from dream to reality

Now that we’ve acknowledged and have a plan in place for the primary constraint to living out your dreams, let’s focus on the crux of the issue: what does your ideal day look like? And how do we get there?

The answer’s simpler than you’re probably thinking and can be broken down into these five steps.

1. The Target: Define your ideal day

The first step is to discover what fulfills you. It sounds so elementary, but surprisingly, many of us go through life without actually knowing the answer to this question.

a. What would you do if you retired today?

Write down (or speak into your phone, if you are THAT person) what you’d do on your ideal day from the minute you are awake until you go to sleep.

Setting aside eight hours for sleep a day, you have at your disposal sixteen full hours every day to spend as you wish. Of course, your ideal day could be anywhere on the spectrum—from binge-watching every Netflix show alphabetically to becoming the next Mother Teresa or somewhere in the middle.

It’s your life, after all, so feel free to go hog wild. Oh, and one other thing, please be honest and a bit realistic.

If you dream of waking up at 3.30, running 15 miles, followed by a green smoothie and enlightening meditation, then don’t forget to include the 3-hour afternoon nap followed by binge-watching in the evening because that’s all your body will allow you to do.

Your ideal day is not just something to put on Instagram to make you look cool. Instead, it’s a schedule, for your eyes only, designed to make YOU happy.

b. Put your ideal day to the term test

Take the ideal day you came up with above for a spin. Imagine going through the schedule you created for five or more days in a row. Can you see yourself doing those tasks day in and day out, or would you get bored?

You think you want to golf all day or travel the world because it seems cool to say that? But really, is that what you want? Visualize your day. See and feel the day. Do the activities feel right or disingenuous to you?

Repeat this exercise and keep refining your ideal day until you can clearly see some common themes: the four or five things you’re happy to do every day. Those are your passions. They may include hobbies such as golf, reading, cooking, or knitting. Or you may love to travel or volunteer. Or, you may just choose to spend time nurturing relationships.

c. Don’t fake it

If you’re someone who listens to a podcast at 2x speed but then decide that after you retire, you want to be an extraterrestrial intelligence researcher—an occupation where no discoveries have been made in decades (centuries?)—you are going to be frustrated.

Your ideal day shortlist should be activities that float your boat. Don’t fake it. No shoulds on this list. Instead, it’s about finding integrity and aligning with your true self.

2. The Prep: Compare your current lifestyle to your ideal day lifestyle

After defining what your ideal day looks like, the next step is to get a reality check to see where you are vis-à-vis where you’d like to be.

a. How close to your ideal day does your current day look like?

Are you too busy doing things that bear no resemblance to what you’d do on your ideal day?

Do you hate your current job but grin and bear it (okay, maybe not even grin) because you have bills to pay? This is a great time to reevaluate the financial independence tips illustrated earlier in this post.

Or, do you want to set up a nonprofit but have no clue where to start?

b. Bridge the gap. Slowly.

You cannot think about what to do after you retire. You need to start laying the bricks now.

Get the gears moving in your head. Incorporate elements of your ideal day into your current day. But in small steps. But don’t just quit your day job yet. Because. Bills.

If your ideal day involves working for yourself, then spend some time (15-30 minutes) each day dedicated to your business idea. Maybe more on the weekends, if you can.

Oh, but where’s the time, you ask? Everyone has time. For instance, on average, we pick up our phones 58 times a day. That’s a lot of time we spend to see if more junk mail has arrived in our inboxes. Why not redirect the time to something you really want to do?

3. The Reality: Living your ideal day

Hopefully, you’ve cleared your schedule enough to start living out your ideal days partly. Or, you’ve reached your financial goal, and you are finally at a point of not needing to work for a living. Hurray!

Not to be a Negative Nancy, but sometimes when you start living out your version of the ideal day, you may encounter some surprises.

a. Not too rosy

It’s possible for you not to like something you thought you would love. For example, if you think you’d love to travel but start craving routine and the comfort of your bed four days into a trip, then you are probably not going to enjoy being a digital nomad and living out of a caravan.

Missteps are fine. They are simply learning experiences. They allow for the rose-colored glasses to come off.

Years ago, the NY Times published a story of a high school intern who used to work as a money market trader at a prestigious Wall Street firm. Soon, he realized he disliked the cutthroat nature of financial trading and went back to school to study science and become a biology teacher.

An ideal day should be when you want to get out bad the moment you are awake. Instead, if you find yourself curling back under the sheets and dreading the day ahead, then you may want to reevaluate the definition of your ideal day.

b. Ideal days do not mean “no responsibilities.”

There is only one place where daily chores get done automatically without you having to worry about them. Utopia. Last I checked, no one has been there.

On planet earth, regardless of how carefree our lives may seem, we will always have to contend with some day-to-day responsibilities. Acknowledge the reality that your ideal days will still contain some obligations. After that, the world is your oyster.


You may already be doing work that fills you with happiness and joy. Good for you. Or, you may be in an unenviable position where your day isn’t really yours but is actually run by other peoples’ priorities.

Defining and working towards your ideal day will help you acknowledge that your life can be improved and, consequently, motivate you to improve yourself.

If you retire tomorrow and all you can think of doing is to alphabetize your spice rack or arrange your shoes by heel sizes, then life may soon turn out to be like a can of canned cabbage soup—bland.

So, work on defining your ideal day now, and then get started on aligning your dream lifestyle to your current one.

How we spend our days is, of course, how we spend our lives. Annie Dillard.



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