Contentment or Ambition? 14 Questions to Help You Embrace the Tension

I talk life and business with at least five people a week. The icebreaker topics like business growth, creating and selling products, and content marketing usually lead to deeper conversations punctuated by thoughtful silences.As adults, we’ll spend most of our waking hours working. So it’s no wonder that questions about a business opportunity, new job, or career transition dredge up deeper, weightier questions:Who am I?Why am I here?What do I do next?The generations preceding ours wrestled with these same questions, but the answers we attribute to them, fairly or not, often leave us feeling frustrated or unsatisfied: “But I don’t want to spend forty years working toward a retirement I may not be able to enjoy. I want to enjoy my life now, not postpone it.”When people unpack their hearts over lunch or coffee, the desires that emerge have more to do with significance than safety or stability:

• I don’t want to miss my kids growing up.
• I want to do work that matters.
• I’d rather have more freedom than more money.
• “Success” seems like a pretty flimsy thing at the end of the day. I want a tight-knit community, deeper intimacy. I care about purpose more than profits.

Some people have a “there” toward which they are moving. In his “Make Good Art” speech, writer Neil Gaiman calls it a “mountain”:

“Something that worked for me was imagining that where I wanted to be – an author, primarily of fiction, making good books, making good comics and supporting myself through my words – was a mountain. A distant mountain. My goal.”

Photo Credit: Avel Chuklanov via Unsplash

Contentment vs Ambition - The Search for Meaningful Work

Sometimes success can obscure the mountain, at least for a time: “Things are pretty good. I like where I am.” But sure enough, once you have paid off your debt, committed to a relationship, or started a family, profound questions come knocking again.Success can lull us, like so many lotus-eaters, to sleep, and failure can paralyze us: “I can't afford another big loss.” We don’t march toward the mountain. We stand still. We hedge our bets. We mistake strategy for action. The Christmas lights strung up in the rooms of our hearts go out, strand by strand.Now I'll be the first to tell you that finding work that makes you glad, work that challenges and activates you, is a first-world problem.If I had a sick child and no access to medicine, then I’d be thinking about very different things. If I didn’t know where my next meal was coming from, I’d be doing very different things. When poverty in other places pricks your heart, you can respond in one of two ways to your privilege of gainful employment:

1. Try to be content with the work you have; or
2. Exercise your freedom to pursue and choose more fulfilling work.

I know people who dislike their jobs. They ache for a better paying and more satisfying one. Yet, they don't want to be ungrateful, and they feel guilty about being ambitious: “Why can’t I just make the best of it when so many people have so much less? What’s wrong with me? At least I have a job. At what point is my discontentment not my heart waking up but simply a symptom of entitlement?”Learning to be content in all circumstances—in great need and in great prosperity—is a beautiful and uniquely human state of being.But contentment and resignation aren’t the same thing. Deep gratitude for basic human needs, such as food, shelter, clothing, and love, can coexist with a hunger for more.

Should I stop being ambitious to be happy?

So we arrive at the tension between contentment and ambition. Say what you will about Baby Boomers, safety and stability are worthy aspirations. They are the rich, black soil in which culture grows. Think about it: The arts typically don’t flourish in societies where food is scarce.In order to practice true contentment, must you squelch or cauterize all desires? Or can you pull on your creativity, intelligence, resources, relationships, and ambition and push to improve your circumstances?I believe that attachment, to use one of Anthony de Mello’s favorite words, is the quiet killer of peace and contentment. You believe that your happiness can begin at some point near the horizon. When a certain figure with however many sets of zeroes behind it appears in your bank account, you can finally rest and enjoy the fruits of your labor.Certain events or achievements will certainly be cause for great celebration. I want financial independence for myself and for everyone I meet. But I am unwilling to sacrifice the daily practice of contentment and joy for an idyllic future state. I am unwilling to feed Now to Then, to sacrifice what I have to what I don’t, because that is the riskiest investment of all.I believe I am at my best when I’m using my Nows to do more fulfilling work. Austin at his best is in a better position, both Now and Then, to bless other people. I have the privilege to choose my work, most of the time, and I choose to exercise that freedom for the good of others.(Strangely enough, I tend to make more money and thus have more to give away when I’m doing work I really enjoy.)Life isn't safe. Business isn't safe. Relationships aren't safe. In fact, the world is a broken, chaotic place, but a place that I believe is also suffused with light, hope, and joy. Oil floating on water has a rainbow in it. (Forgive the cheesiness of that last statement.)

14 Questions to Help You Embrace the Tension

Perhaps these 14 questions—inspired by my friend Carl Smith’s “Your money or your life? Designing a business that won't kill you” workshop at ConvergeSE 2013—can help you see the best version of yourself more clearly. Pick the five that make you uncomfortable, open your journal, and answer them as honestly as you can.

1. Why am I not doing what I want to do?
2. What is stopping me right now?
3. What am I afraid of?
4. Why isn't my work great right now?
5. For what do I receive praise?
6. Who can call B.S. on me?
7. If time and money didn't matter, what would I spend my days doing?
8. How do the things I want to do benefit others?
9. Does it feel good?
10. What happens if I choose this?
11. How does this affect the people in my life?
12. What are the things you have to do?
13. How am I currently wasting time?
14. What path makes the better story?

Those of us who are in the process of deciding what to do next aren't any less afraid most of the time. But you do stand to lose more in pursuit of comfort than you would have lost to failed ventures and bad investments.If you have the freedom to pursue more purposeful work, then why don’t you? Choose your harbor, then pick your wind.

“If a man knows not what harbor he seeks, any wind is the right wind.”– Lucius Annaeus Seneca

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