Make Major Life Decisions With Confidence By Answering Three Simple Questions

Making Small and Big Life Decisions Will Be Easier Once You Journal and Reflect On Your Future

A close friend asked for my advice: Should I take a job a Company A or Company B?

She just finished sharing all the pros and cons of both decisions with our group of friends. Three friends voted for Company A and three other friends voted for Company B. I was going to be the split vote.

This moment was exciting. All eyes were on me. What was I going to say?

I did what any normal person would do: I asked her some hard questions.

After digging deeper into her situation, it became abundantly clear that both choices were not what she actually wanted in the first place. She felt much more drawn to be a freelance designer than to work at either of those corporate jobs.

I just saved her 5+ years of her life. You're welcome!

My group of friends looked at me as if I was some wizard. But in reality, the answer felt quite obvious to me because I've spent so much thinking about how I want to live my life.

I'm proud to have made several "big" life decisions quite confidently.

• Dropping out of college to apprentice under startup founders around the Bay Area
• Leaving my old friend group to find new people who shared similar values
• Quitting my job to study chess full-time for seven months
• Moving from the Bay Area to Toronto without knowing anyone in Canada

While these transitions were incredibly difficult and uncomfortable, pulling the trigger on these decisions felt easy and familiar.

There are three questions that I filter the majority of my big life decisions. The answers to these questions make it easy for me to know what opportunities to say yes and no to.

Have a paper and pen handy because I'm going to invite you to journal on your answers to these questions. Let's dive in.

What is your perfect day?

Chess Grandmaster José Raúl Capablanca once said,

"To begin, you must study the end."

Capablanca used his deep knowledge of chess endgames (the "4th quarter" of the match) to determine what move he should make in the middlegame.

While your goal in life isn't to checkmate your opponent, I love this quote because it is a metaphor for how we should live. My translation:

"In order to make wise life decisions, you must think deeply about what you want your ideal life to be."

I'm not suggesting that you should map out your entire life in a predictable timeline and magically live happily ever after. Life doesn't work that way.

Instead, it would be simpler and more practical to zoom in on a simple day in your life. Because guess what? Your days are your life.

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

What is your perfect day?

While this may seem simple on the surface, it is in these details where we will find how we spend our most valuable resource: time.

How do you want to spend it?

Say you love to cook and spend time with your kids. But I come to you with an exciting opportunity to be a part-owner of my new restaurant. Should you take it?

It sure sounds tempting. Your neighbors will envy you for being part of the hip new eatery in town. You might make money if the restaurant succeeds. Plus, you will even get a dish named after you.

But what will this new job actually entail? Long, stressful hours to build the restaurant from scratch. Meetings with construction, interior designers, and new team members. A big chunk of change from your own pocket as an initial investment.

Then once the restaurant is up and running, you are still working hard to market your business, hire new people, and deal with annoying customers who hate your food.

Does this new role get you closer to your perfect day? You haven't had uninterrupted quality time with your kids in months. You never cook for yourself anymore because you are always working. And you never get to see your husband or friends like you once used to.

I'm guessing the answer is no, this opportunity does not look like it is getting you closer to your perfect day.

If you like to cook and spend time with your family, you'd probably be happier being a cook at a restaurant instead of an owner.

Once you know what your perfect day looks like, evaluating the opportunities that come your way becomes much more clear. Later, you can design what your perfect week, month, and year look like. But for now, let's KISS (keep it simple, stupid).

Journal Prompt: What does your perfect day look like?

• When do you wake up?
• What foods do you eat?
• What are you working on?
• Who do you see?
• What hobbies are you enjoying?
• How do you spend your evenings?
• What are you NOT doing?

You can see my answer to this question (along with the other answers) in the second half of this essay for an example.

What are you willing to struggle for?

As you design your life, your days will not be perfect.

In fact, your days will probably be full of hardships and struggles, but this is a GOOD thing!

Hold on  Tam... You just told me to optimize for my perfect day. Now you're saying it's not going to be all sunshine and rainbows?!

Let me explain.

Asking someone, "What do you want out of life?" is vague and unhelpful.

You might say, "I want to be happy and have a great family and a job I like." that doesn't tell us much. A more interesting question that most people never consider is:

What are you willing to struggle for?

"People want an amazing physique. But you don't end up with one unless you legitimately appreciate the pain and physical stress that come with living inside a gym for hour upon hour, unless you love calculating and calibrating the food you eat, planning your life in tiny plate-sized portions.

People want to start their own business. But you don't end up a successful entrepreneur unless you find a way to appreciate the risk, the uncertainty, the repeated failures, the insane hours devoted to something that may earn absolutely nothing.

People want a partner, a spouse. But you don't end up attracting someone amazing without appreciating the emotional turbulence that comes with weathering rejections, building the sexual tension that never gets released, and staring blankly at a phone that never rings."

As it turns out, problems never go away in our lives. They get exchanged and/or upgraded to new problems. So we shouldn't hope for a life without problems. Instead, we should hope for a life full of good problems.

If you're lucky enough to do so, you can live a more meaningful and fulfilling life by choosing the pain that you want to sustain.

When you are thinking about your next big life decisions, ask yourself: Will the struggle be worth it?

If it's not, great! There is an opportunity in giving up on your dream. If it is worth it, then go after it, and embrace the struggle along the way.

Journal Prompt: Write down what 5 things you want to suffer for. Write down 5 things that you want to give up.

You may want to suffer to be a great parent or to get promoted in your job because your family and career are important to you. After journaling and reflection, you may change your mind and choose not to suffer for that fancy new car or having six-pack abs.

Don't think too hard about this. Write down what is coming up for you and explore your answers with curiosity.

Question credit goes to one of my favorite books, The Subtle Art of Not Giving a F*ck by Mark Manson.

How do you want to feel?

Let's forget about our dreams for six-pack abs, $10 million dollars in the bank, and showing off your hot girlfriend to your friends.

Let's focus on something more exciting: our FEELINGS. 💖

If you forgot what emotions are, here's the famous Feelings Wheel for you to gander.

When you close your eyes and visualize yourself living your ideal life, how do you want to feel every day?

Do you want to feel confident? Joyful? Curious? Peaceful? In awe? Aroused!? 👀

When you make a decision, you can see what options evoke the emotions that you want to feel.

• If you want to feel adventurous, maybe you should go on that solo travel trip that you've been holding back on.
• If you want to feel creative, maybe you can talk to your boss about how to bring more of that feeling out in your work.
• If you want to feel playful, maybe you should ditch that boring accountant boyfriend and go out with someone with more gusto for life.

Journal prompt: Write down 5 emotions on how you want to feel when you are at your best.

This question was inspired by my friend Jennie's amazing Google Slideshow (yes, you read that right) on self-care.

Tam's answer to "What is your perfect day?"

My perfect day is simple.

I wake up naturally feeling refreshed and energized. I meditate and write in my Five Minute Journal. I eat a healthy breakfast and go for a walk. I make some Vietnamese coffee before getting started on work that I care about.

I spend a few hours either writing a new essay (like this one), designing a program, or teaching a class/coaching a student. Since I am most productive in the mornings, I prioritize these projects over everything else.

If I can get a solid three hours of deep work in before lunch, I feel like I've already won the day. Everything else will feel like a bonus.

I eat lunch solo or with a friend. I do some "admin" work and go to meetings if needed. Fortunately for me, my small team has everything under control. I end work around 4pm and go work out or do some yoga.

My evenings are exciting and full of variety. I can have a patio dinner with friends. Or you can catch me dancing bachata/salsa, taking an improv class, trying Muay Thai for the first time, biking around the city, or on a hot date!

I turn my screens off at 9pm and start to wind down: hot shower, stretch, read, Five Minute Journal, and sleep.

Interesting takeaways:

• I don't want to spend my entire day working so I would be a horrible lawyer or banker.
• I like being creative so I spend most of my time, well, creating. I say no to unnecessary meetings as often as possible.
• I love my hobbies and meeting new people. This means I want to live in a city where it's easy to go to events and have a job that keeps my evenings and weekends free.

Having this lifestyle is not easy for the average person. But I choose to struggle for my ideal life because it is worth struggling for.

Tam's answer to "What are you willing to struggle for?"

I am very fortunate that in my life, I've had the opportunity to choose the majority of my problems. I've fully embraced my blessed life and have used it to lean into my deepest fears in pursuit of personal growth.

• Working my butt off for 7+ years to collaborate with my dream mentors. This journey required me to drop out of college, be isolated from my "normal" friends, and work extremely hard to build skills from scratch. I had the learning opportunity of a lifetime to apprentice under the people that I've read about in books or listened to in podcasts. It was worth the struggle and I don't regret anything!
  
• Facing my childhood body image and self-worth issues. I truly hated my body and had an evil relationship with how I spoke to myself. I saw a therapist for the first time in my life and we opened the door on many areas of my upbringing that I've repressed and ignored. The exploration, daily practices, and tears shed were worth it. I went from hating myself to feeling so much more love for myself. Wow.
  
• Dancing Bachata aka partner dancing. This is something that I've been incredibly scared to do because (a) I was not a good dancer and (b) I am deathly afraid of looking stupid in front of attractive women. I went from begging my best friend to take my first class with me, to leaving a social before it even started, and eventually dancing three times a week and loving the journey. It took me a year to finally feel comfortable moving my body and yes, the pain was worth it. (You can see me dance here)

I've had many more experiences like these but you get the point.

After internalizing this question, I live for the struggle.

I know that whenever I'm being challenged or pushed to my edge, I experience the biggest personal growth. I feel proud of myself for having the courage to go do the "hard" thing and I always end up feeling like I'm living the best version of my life when this happens.

This doesn't mean all my problems have gone away. I got new problems in different areas of my life.

This doesn't mean I don't get scared. I experience fear all the time and it never gets easier but instead, more familiar.

While the results are nice, what is more important is the climb.

Because the joy is in the climb itself.

Tam's answer to: How do I want to feel?

The emotions I feel most drawn to today (your answer to this question may change in a different time of your life) are:

• Energized
• Challenged
• Aligned
• Joy
• Love

I often use these emotions as a filter for decisions.

• Will meeting with this old friend give me energy?
• Which direction sounds more challenging to me?
• Does this new project feel aligned with my values?
• Will this new hobby bring me joy?
• If I fully loved myself at this moment, what would I do in this situation?

Final Thoughts

Once you know what you want, making big (or small) life decisions become quite simple.

I want to stress that just because something is simple does not mean it is easy.

Saying no to two stable job offers that will make your parents proud and your current friends more accepting of you... can be difficult to turn down.

Doing the courageous thing, your ability to do the thing that scares you the most is in my experience, often the most rewarding. I hope you choose the path worth taking.