journal on a table

6 Questions to Radically Change Your Life

JessieAuthentic Business 4 Comments

You don’t need to be a ‘digital nomad’ to chase what’s most meaningful.

Unhappy with your job? Bummed about your prospects? Tired of whatever it is you do every day?

There are a million self-help articles that will tell you to try this or that to make yourself happier. In all honesty, I’ve probably written a few myself. But outside of all the tips and tricks is the fundamental truth that your life is yours, if you choose to claim it.

Today, I wanted to share a few journaling questions that I return to constantly. These questions keep me grounded, and they have the potential to radically change the way you view your own life.

Now, before you dive in, let me say: There are some potentially off-putting ideas in here. We’re going to talk about money, and people get weird about money. We’re also going to talk about what makes you happy, which tends to freak people out as well. These questions are tools, and I encourage you to use them only insofar as they help you.

Question 1: What are your responsibilities?

A lot of articles like this tend to focus on happiness above everything. That IS the ultimate goal, but I think it’s important to also recognize the real responsibilities we have to the people around us. For example, running off to another country might make you happy… but might be more complicated if you have a spouse or kids to consider.

So before we dive into happiness, let’s start with the non-negotiables:

First up, what are your interpersonal responsibilities. Who is important in your life? For each person, list what they need from you. This might be financial support, time spent together, or guidance in certain areas.

Next, let’s talk about financial responsibilities. How much do you need in order to continue your standard of living? Write down the number—including housing, food, entertainment, necessities, debt payments, etc. (If you’re not sure, it’s time to dig into your bank account. I won’t lecture you about that here, but understanding where your money goes every month is the first step to any kind of financial change).

And finally, write about your aspirational responsibilities. What financial or interpersonal responsibilities would you like to have, and how do they vary from your current situation? Maybe you want to spend more time at home, or you wish you could make extra income to pay down debt faster, or you want to start investing.

man reading a picture book to a baby

Photo by Picsea on Unsplash

Make it your goal to quantify as much as possible. How much do you have, and how much more would you like? Would an extra 30 minutes a day with your family feel like a major success? Do you wish you could spend most of the day with them? How much more money would you need to take care of your responsibilities?

Write it down. It might be painful if you find your ideals don’t match reality. Write it down anyway.

At the end of this step, you should have a hefty set of notes. How you structure them is up to you, but it should give you a clear picture of where you are money- and time-wise, and where you’d like to be (at this point).

And a final note: Although I’ve called these responsibilities “non-negotiables,” the reality is that everything is negotiable until you choose to make it non-negotiable. You are bound to nothing except what you choose to be bound to. Make sure each responsibility you take on is something you choose.

Question 2: What are the top 10 things that make you happy?

With the external factors in place, it’s time to look internally.

What makes you happy? What activities, events, or even purchases made you think “Wow, I really like this. I could do this forever”? What do you want more of in your life?

Write down the top 10 or so things that bring you contentment. No judgement here. Don’t try to censor yourself or overthink. Just make a list.

Here are mine, in no particular order:

  1. Eating good food with my husband
  2. Having friends over for parties (ideally, in a nicely decorated home)
  3. Planning and strategizing new ideas for my business
  4. Helping people with their businesses
  5. Working with my hands—refurbishing furniture, art, etc.
  6. Group camping trips in beautiful places with good people
  7. Going on fun dates with my husband
  8. Having meals with my family
  9. Sitting by my parents’ fireplace on cold mornings
  10. Going on (and preparing for) trips

Your list may look very different from your present reality. If so, don’t worry—that’s kind of the point of this whole exercise.

Now, look over the list. What would it look like to add each item to your life?

For me, it would look like:

  • going out to eat at least once a week,
  • visiting my parents at least twice a month,
  • taking on a hands-on project once a month,
  • hosting a few events each year, and
  • going on a trip or two each year.

By choosing how often you’d like something to happen, and in what way, general desires take form into clear goals. And now, you can add a monetary value to each item.

How much would it cost, either per month or per year, to do or have the things that bring you the most happiness?

Map it out.

Combined with your responses from Question One, you should begin to have an idea of how much money your lifestyle would cost if it was composed of your ideal responsibilities and the things that make you happiest. At this point, two things can happen:

You find you have enough money right now to enjoy the things that make you happy

Congratulations! Now, your challenge will be to find the time to enjoy those things.

You find you need to make more money

Congratulations! Now you have a tangible number you can work toward. Money is just a tool. And now, you know how to use it to literally buy happiness. At least partially. (Read on)

Question 3: What’s holding you back?

In self-help circles, there’s an understanding that happiness is our natural state. Finding happiness, then, is about removing the barriers that keep you from that state.

I won’t tell you that happiness is 100% a frame of mind. Yes, you can choose to be happy at any point, but let’s be real: Some situations make it tougher than others.

Instead, I think of it more like a ratio. Happiness is partially about removing external barriers, and partially frame of mind. The exact ratio varies from person to person.

External barriers

External barriers to happiness might include people, jobs, or situations that bring constant stress into your life. List out what’s bugging you or bringing you down. These are the items that you can eliminate, negotiate, or choose to live with—but make sure it’s a conscious choice.

Internal barriers (frame of mind)

The internal barriers are just as tough. Personally, my barriers to happiness at one point were feelings of loneliness, regret, and inadequacy. Even when my circumstances eventually changed for the better, I found that I still needed to do some internal work to feel the full benefit.

And you know, the process likely could have been sped along with a therapist. Therapists are awesome.

Question 4: Where do you want to exert your effort?

Happiness is very, very important.

However, it’s a dynamic concept. Sitting around eating good food all day may make you happy on a basic level, but a sense of meaning and purpose, I think, comes from the effort you put toward something.

Where do you want to exert your effort? What do you want to accomplish in this life?

It doesn’t necessarily have to be something world changing. Maybe you want to put your effort toward loving and supporting your family. Maybe you want to just get really good at a particular skill. Maybe it’s a few different things—that’s probably more realistic, anyway.

One of my favorite concepts comes from Mark Manson (who actually got it from Liz Gilbert). The concept asks: What kind of shit sandwich are you willing to eat?

In other words, every activity worth doing comes with hardship. What kind of hardship are you willing to endure?

I think this question is closely tied to finding your why. It’s about finding what matters to you.

Question 5: What does your ideal day look like?

Now that you’ve mapped out what makes you happy, what’s holding you back, and what you want to accomplish—how can you plan your life to reflect those ideals?

I believe that if you can do it for a day, you can do it for a week. And if you can do it for a week, you can do it for a year. Rather than setting huge goals about what you want your year to look like, just focus in on your perfect day.

We’re talking about work days, specifically. That said, I personally strive to create a work life that I love enough to want to do it on the weekends as well—but that’s completely up to you.

In an ideal day, what time would you wake up? When would you start working? What would you do for work? How would your day end? How would you do more of things you love doing?

I don’t care if it looks nothing like your current life. This is aspirational. Go nuts.

You can write this in long form (“In the morning, I wake up at 7am and…”) or time block it out:

7am-7:30 Wake up and shower

7:30-8:00 Breakfast and journaling


Include variations if needed—maybe you want to do some things some days, but not every day. The point is to get your ideal day on the page.

Dog laying on a bed while woman works on a laptop

Photo by BRUNO CERVERA on Unsplash

Your ideal day is your new goal. It takes into account your responsibilities, what brings you happiness, and what you want to accomplish. Now, you can ask the most important question:

Question 6: What do you need to do to make your ideal day a reality?

For each element of your ideal day, write out what would need to change from your current situation in order to make it work. It might be as simple as going to bed on time so you can wake up earlier. It might mean a career change. It might mean devoting more (or less) time to certain relationships. It might be going out and striking up new relationships altogether.

It might also mean a lot of research.

These are just questions to get you thinking. Let these pages serve as your brainstorm and guidepost as you figure out the path forward.

Creating a life you love IS possible. But you are the only one who can create it.

“Tell me, what is it you plan to do with your one wild and precious life?” – Mary Oliver

Feature photo by Bookblock on Unsplash

Comments 4

  1. I loved this so much I printed it out to work through with my husband. I’ve read entire self-help books that are way less on-point than this. Can you write this into a book in your free time?

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      Mark this day as the day someone asked me to write a BOOK! Popping the champagne tonight 😉

      Thanks for your kind words Jenn—I’m so glad it’s helpful to you guys!

  2. I am really glad i got to read this post, i have been struggling for a while with my choices, and after reading this, i can say i have an idea of the decisions i need to make in life. Thanks a lot Jessie

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