What I Learned From Gretchen Rubin’s Paradoxes of Happiness


Note: This is a post from Courtney Baker, chief seller and long-time running wo-man of MvD.

For several months now, I’ve been conducting monthly challenges.

They’ve included writing every day, not cooking for a whole month, calling old friends, leaving yelp reviews for businesses I love, walking 10,000 steps a day, tracking my expenses, giving ‘Gold Stars’, and organizing my spaces.

It’s been a fun adventure that has revved up my life! But, it’s hasn’t always been easy. Do you know how hard it is to walk 10,000 steps when it’s 35 degrees outside? I may or may not have spent a few evenings jogging circles around my living room!

Part of me wanted to create a challenge and actually stick to it. But mostly, I wanted to boost my happiness. It’s not that I’m not happy, I’m just trying to be even happier.

See, I’ve developed a lady crush on author Gretchen Rubin.

Like most of us, Gretchen realized that she wanted to “be happy”. But she wasn’t focusing time on understanding what made her happy or spending time doing those things. Thus, The Happiness Project was born. She explored happiness in various area of her life – work, marriage, parenting, exercise, friendship.

Gretchen realized that being happy was a difficult goal, because happiness is a process, not a destination. We should strive to be happier. This past fall, she released her follow up book Happier at Home.

In all her explorations, she always landed back on this list of paradoxes. Gretchen wrote this list specifically for herself, but I’m convinced she wrote them for me!

It’s amazing how well they apply to everything- even finances! Use this list to get revved up to pay off your credit card, clear out your attic, or finally pursue that things you’ve always wanted to do.

Paradox #1: Accept myself, and expect more of myself.

When we first started our debt journey, it was hard to admit how much debt we had. We felt stupid and embarrassed. The guilt was so overwhelming we could hardly do anything about it.

It wasn’t until I embraced my past as being a part of my story. I had a choice to change what I didn’t like and create a better story. I expected more from myself.

Paradox #2: Give myself limits to give myself freedom.

One of our most powerful budgeting moments was when we started budgeting fun things. For the longest time, I felt horrible about eating out, taking vacations, or buying new tech-toys, because ‘”we shouldn’t be spending money”.

Once we established how much money could be spent in these categories, it felt like we had the world. Without those boundaries, I probably would never buy myself new clothes. These limits give myself permission or freedom to go for it.

Paradox #3: Make people happier by acknowledging that they’re not feeling happy.

The other day, I was having one of those days. Unfortunately, it was a little more apparent than I would have liked! A stranger chuckled, “Rough day?” The conversation didn’t go beyond that, but his small acknowledgement alleviated the situation enough for me to get over the day.

We love connection, and simply saying “Hey, I get it. That sucks.” is all we need to hear. It also takes away the judgement.

Saying “Ya know, tracking your expenses can be so hard to keep up with.” is incredibly empathetic and could give a person the boost they needed to keep going.

Paradox #4: Plan ahead to be spontaneous; only with careful preparations do I feel carefree.

As much as I hate to admit it, spontaneous dinners and events stress me out financially. I feel torn between going with the flow and panicking about how much money I’m spending.

If I maintain my budget, then I know my boundaries and can participate in spontaneous activities without that lingering stress.

Paradox #5: Accomplish more by working less.

It’s amazing what kind of inspiration you can find when you step away. Just last week, I was working on some writing project and getting nowhere. I wanted to get done in time to go for a trail run. Instead of sacrificing my escape to the outdoors, I scrapped writing and went out. While I was running, I had a million ideas come rushing in for my article.  When I went home, I finished the project in a third of the time.

Sometimes we need to get out and enjoy things to find purpose in our work. When we have purpose in our work, we tend to do it quicker and better.

Paradox #6: Happiness doesn’t always make me feel happy.

Paying hundreds of dollars a month to student loans will not make you feel happy, but chipping away at a mound of debt does. That single monthly payment can feel like torture some months; but in the course of the year, it’s such a relief to see those balances going away.

Paradox #7: Flawed can be more perfect than perfection.

I have a story. It’s not a pristine story, but it’s beautiful enough. Honestly, nothing has helped me realize this more than having kids. I love Milli for the imperfect drawing she makes and imperfect grammar she uses. Our imperfections make us different. They make us human.

Paradox #8: It’s very hard to make things easier.

My ears burn when I hear people talk about the “calories in, calories out” diet. It’s simple, right? No! There are a million decision you make every day related to food. You have attitude, stress, and sleep adding to the equation too. It’s hard to simplify to some in-and-out ratio.

Finances are the same. You just “create a budget and only spend the money you have.” Easy, right? No! It takes discipline to track everything, control your spending, and avoid impulse purchases.

Paradox #9: My material desires have a spiritual aspect.

Our thoughts on spending, consumerism and needs are driven by how we feel about humanity, community and fellowship. I seem far more satisfied with my life and possession when I’ve been volunteering for less fortunate families. My sense of entitlement increases when I’ve been completely absorbed in my own life, oblivious to those around me.

Paradox #10: Hell is other people. Heaven is other people.


Sometimes people are infuriating (ahem, customer-service people, ahem), and sometimes people are awe-inspiring. You have to take your chance. You might find a few bad eggs along the way, but then you’ll stumble across a golden conversation. For me, those conversations are what propel me to become better.

Recently, I relented and took Milli to the park for 10 minutes to burn off some steam. I had a huge to-do list and didn’t want to stay long. An older African woman struck up a conversation with me on the park bench. It turned into an hourlong conversation about how happy African people are, traveling adventures, and how her mom raised her.

My to-do list became non-existent, and I replayed our convo for weeks afterward. People make the world worthwhile!


I’ll bet my lunch that you exclaimed “Exactly!” for a couple of those paradoxes. They really do apply to all things relating to life and happiness whether its finances, relationships, or fitness.

How have these paradoxes been true in your life? Have you participated in your own Happiness Project?

Comment below!

14 thoughts on “What I Learned From Gretchen Rubin’s Paradoxes of Happiness”

  1. I find I definitely need to be truer to myself, and I’m thinking I’ll be adding this to my list of things to read, too – very soon.

    I am someone who has to plan to be spontaneous, like you. I hate surprises. They give me anxiety. I want to feel secure and in control!

    1. I think both books are great. The monthly challenges have turned into a fun little game for me. Make change much more enjoyable! And you can embrace that being in control makes you happy.

    1. That is a good article and the book is a great inspiration “It is the very pursuit of happiness,” Frankl knew, “that thwarts happiness.”. Gretchen also talks about this. When I am happier, people around me are also happier. This gives meaning.

      1. I don’t necessarily agree that the very pursuit of happiness thwarts happiness. For me, a constant pessimist and an extremely cynical soul, happiness is hard work. My #1 Personal Commandment, inspired by none other than Gretchen herself, is “Happy is a choice.” That, to me at least, means I must take actionable steps on a regular basis to bring more joy into my life, to call myself out when I’m being pissy, to talk myself up when I’d rather be down. I’m a regular Eeyore, trying to be a Jokey Smurf, and it’s pursuit of such that has pulled me out of the worst depressions. I would argue that OBSESSION with the pursuit of happiness might thwart happiness… as obsession is wont to do with anything. Part of the pursuit of happiness, of course, is learning to enjoy each moment, to take one day at a time, and to roll with the punches – in essence, to STOP pursuing so dang much. This is yet another paradox of happiness, methinks.

  2. I loved this email! went straight to kindle and searched out Gretchen Rubin’s books. 🙂 Thanks for the introduction, i can’t wait to get reading.


  3. I love Gretchen’s book. Have not started on my own monthly challenges although I cleaned out my wardrobe and office 🙂

    Beautiful list of Paradox and how they fit for you Courtney.

  4. Other people really can be heaven or hell. It seems that the better you know someone the more they can hurt you, but also the more you stand to gain from the relationship. Friendships are a double edge sword, but they also add the best things in life.

  5. Hi Courtney, I loved your post. Paradox #4 resonates with me because we so often fail to plan ahead when it comes to our finances. Budgeting or simply tracking your expenses is a great way to get a grip on the month-to-month costs, but so many people fail to plan for the bigger ticket items, like saving for a new car to replace the one that WILL eventually wear out. Or, just to plan for car repairs, or semi-annual insurance payments, etc.

    Once I started saving monthly (actually some from each paycheck) to cover these inevitable costs, my life changed dramatically (less stress=greater happiness!). I never had to worry about where the money would come from. I talk about this in a post I just published called Part II: Does Your Spending Support Your Values? on http://www.EscapingDodge.com. In the post is a simple two-page spending tracking worksheet that has categories for these types of expenses (it’s free and I’d welcome feedback on how it works for people.)

    Thank you for the great content on Man vs Debt!

  6. I totally needed this reminder! Thank you! I’m finally living my dream life in the caribbean but believe it or not I still have some of the same challenges I did at home. I’m just realizing again that happiness comes down to the little daily things. For two years I’ve been looking ahead to this life and thinking I will be so much happier once we have accompolished it. I am happier and so grateful for my life but I still need to work on my daily happiness.

    Since baby number three my life is pretty much just kids, cook, clean, and stay awake no matter where I’m living. I’ve got the big thing now it’s time to work on the little things.

    Oh yeah and I love reading so I’ll definitely buy the book.

  7. #5 – Accomplish more by working Less.

    This is the one that I completely believe but have a difficult putting into practice most times. Thanks for the reminder 😉

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