5 Thought-Provoking Questions to Love the Job You’re With: Advice from Good Life Expert Jonathan Fields

5 Thought-Provoking Questions to Love the Job You’re With: Advice from Good Life Expert Jonathan Fields


“When you align what you do with who you are, you’ll become what you need to be.” –Jonathan Fields

For as long as I can remember, I have been deeply fascinated with why we do what we do. However, making complex things simple is some of the hardest work out there! It takes digging through the weeds and getting to the root of what’s really going on.

And when dealing with challenges that come up in life, that often means facing a part of ourselves that we may not want to face… In a sense, life’s challenges are usually a chance to look head on at yourself—and as a result unveil parts of you that might be hidden.

So, given the circumstances over the last year, I have spent more time than normal facing myself head on, trying to understand why I am motivated (or not) to do things, and trying to break down the complex into more simple terms. I have found that the question I most often ask myself is:

“What is really going on?”

This question helps me distill things down to a deeper level—and to get rid of all the external things so I can better understand the internal things.

Because the truth is, if you ever think anything is about something outside of you—people, environment, etc.—it usually tracks back to something that is really going on within you. When you take a deep look, most of what’s presented as something going on around us, really has to do with what is going on within us.

And I had an interesting realization recently when I thought about this idea of simplifying all the complexities that come up with major life changes and challenges. When I broke it down, I realized that it was actually quite simple…

In order to honor Scott, myself and all those around me, all I have really done is chosen to continue to live a good life, even when life thoroughly challenged me not to.

Now it is important to note that simple does not mean easy! They are not two sides of the same coin. In fact, they are very opposite. But when you break it down to the root of things, that is really all I have chosen to do. 

“But wait, what?” you might be thinking. ”Are you telling me that living a good life is simple?!”

Haha, not at all. Which is why, today, I am so very excited to share some advice from a beautiful being that I consider a friend, mentor and is most certainly a good life expert…

What Does It Mean to Live a Good Life?

*Note: I held a free Q&A with Jonathan about all things good life related! 


I’d been hearing good things about Jonathan Fields from Scott for quite a while.

But Scott really piqued my interest about Jonathan when he came home one day and asked me, “Chelsea, what does it mean to you to live a good life?”

While Scott and I had anything-but-ordinary dinner table conversations, that seemed to be quite a big question for an average Monday night… I was clearly curious why he came home with such a thought provoking question—and he mentioned that later that week he’d be doing an interview with Jonathan—and “What does it mean to live a good life?” was the final question he’d be asked in the interview.

That is by no means a simple question, right? Some might argue that it is actually the biggest question we will come across in life—and what we are all here to discover…

Scott and I bounced some ideas back and forth and collectively came up with an answer that went something like this to that big ol’ question:

“To live a good life means to spend your time doing what you love, with those you love, in a way that leaves the world a little bit better.”

Live Your Legend: How to Live a Good Life

Making the Complex Simple

So how do you possibly begin to distill this big life question down into something simple?

Well, I don’t think many could, but Jonathan certainly has done that and more in his new book How to Live a Good Life: Soulful Stories, Surprising Science and Practical Wisdom.

I was lucky enough to get an advanced reading copy—and gobbled it up so fast, I could barely think of anything else while I was reading it. Because well, as I mentioned, I am kinda obsessed with:

  • Understanding what’s really going on
  • Finding simple actionable ways to constantly, learn, grow, give and generally be a better version of me

And in this book Jonathan has done an absolutely brilliant job of educating us how to “do more, be more, give more and live more.” He has broken down the idea of living a good life into a simple framework of 3 buckets that must be filled:

  1. Vitality Bucket
  2. Connection Bucket
  3. Contribution Bucket

He then breaks down each of those buckets into 10 different ways to fill them, alongside simple “daily explorations” that are actionable takeaways you can begin to implement on the spot.

I honestly don’t know how he did it, but he created a simple, step-by-step guide to answering one of life’s most complex questions. Go JF!

Why Living Your Legend Is Key to Living a Good Life

And it should be no surprise that the topic of doing work you love is one of those key components to living a good life, right?

That’s why we do what we do here at LYL! Because a lot of us spend the majority of our days at work. And if you spend the majority of your time doing something that drains instead of fills your buckets, that is going to subtract instead of add to your overall good life.

So I am honored to introduce Jonathan to talk about why living your legend is essential to living a good life.

Take it away Jonathan…

I’m so excited to share this conversation!

Simple fact, a good life is a life of meaningful contribution, deep connections and abundant vitality. It’s also one where we tap our strengths and abilities to stand in our full potential, feeling like every ounce of capability is being mined to the max, and we’re fully-expressing who we are. The the work we do—whether paid, out of love or volunteerism—can cultivate all these experiences and end up filling all three Good Life Buckets.

When we choose well, our work can be a profound source of meaning, creating a sense of purpose and passion, like we and what we do matters. It can also cultivate endless opportunities to tap our strengths and abilities, these are a blend of what we’re good at and our deeper virtues. Research shows than when we work from this place, we light up. Life gets better, even if the work is hard and there is struggle along the way.

Beyond that, work is also an opportunity connect on multiple levels, building friendships, partnerships, collaborations, community and being in service of others. This sense of connectedness, belonging, companionship and, sometimes even love, is transformative on so many levels.

So, while work is not the only way to fill our Good Life Buckets, it certainly can be one of the most powerful.

So given the importance of this topic, today we share with you one of the “daily explorations” directly from How to Live a Good Life. We encourage to you take some time to really think through these 5 questionsbecause loving your work is key to living a good life—and in the end, that’s all we are really after, right?

How to Love the Job You’re With 5 Thought-Provoking Questions

  1. If I believed with every fiber of my being this was the work I had to do until the job was done, that there was no way out, no bigger, no better deal, what might I do to make it as good as it could possibly get?
  2. What relationships might I work harder to build, mend, deepen, or expand that would allow me to experience this work with more ease, grace, confidence, strength, meaning, purpose, lightness or joy?
  3. What specific tasks and responsibilities would I give up, hand off, or do differently that would make a real difference in the way I experience this work? What new tasks and responsibilities might I take on?
  4. Is there a bigger purpose or community or person (or Divine source, however you might describe it) I am deeply connected to that the work I am doing is serving?
  5. How might I build my non-work life around what I do in a way that lets me frame it as a source of greater meaning, joy, connection, and engagement or something that gives me freedom to do other things that provide those feelings?

This is just a glimpse at what Jonathan’s book offers—just one of the 30 topics he covers about how to fill your buckets and live a good life!

Now, can you see why I ate up the book?!?! You have the opportunity to pre-order your copy today. I promise you will not regret it!

And if you want to hear a bit more from Jonathan and all things good life, please join us this Thursday for a free Q&A where Jonathan and I will jam about:


  • His process and “why” behind writing this book
  • My favorite thoughts, quotes and takeaways
  • How living a good life directly relates to living your legend
  • And much, much more!

Here’s to discovering the good life that’s available to all of us,

–Chelsea Dinsmore