“Okay, I’m not fulfilled. Now what?”

During intermission at Sum and Substance Seattle, I had a couple of conversations with people who were clear that their current work was not fulfilling, but were very unclear about what would be more fulfilling. I’d like to share four ideas that I’ve encountered recently that may help.

#1 It’s okay not to know what you want to do.

In his wonderful book The Three Marriages, author David Whyte explores happiness and fulfillment in life. The central idea is that there are three life-long commitments we all make: our relationship with ourselves, our relationship with a romantic partner, and our relationship to our career. Whyte holds up as the ideal a state in which all three marriages are not separate distinct spheres requiring each to be ‘balanced’ against the others, but rather a synthesis between all three.

Whyte makes a beautiful case that finding work that aligns with what you truly enjoy and care about in the world (self), and finding a partner who has not only found that work for themselves, but who can be just as passionate about your work and vice versa is true happiness and fulfillment for human beings.

He argues that this isn’t a fairytale scenario where you magically become enlightened, find your soul mate and dream job and live happily ever after. Each of the three ‘marriages’ requires constant maintenance and attention – but he argues that when all three align, that maintenance is itself a deep expression of who you really are, and as such is deeply fulfilling.

Fortunately Whyte also recognizes that many of us are still working on locking those things down one at a time – just as he did as a younger man.

“All of us face the same dynamic in our work. There are lots of actions we could take to peruse a work or a career, but we often don’t begin because we don’t feel the grip, the connection, the current that can carry us across suck a wide tract of water. In effect, we leave the beckoning blank page of out life completely empty because we don’t have the confidence in the particular first sentence that confronts us.”

I think this may be the passage that best captures the feeling I heard from the people in Seattle who just don’t know where to start on their journey to fulfillment. If you find yourself in a place of just plain not knowing, you may actually be ahead of most people.

“Eventually we realize that not knowing what to do is just as real and just as useful as knowing what to do. Not knowing stops us from taking false directions. Not knowing what to do, we start to pay real attention… only those who put more energy into self-pity than paying attention are truly marooned.”

Whyte argues that many people are not sufficiently in touch with ‘self’ and so put on a brave face: ‘sure I love my job! Livin’ the dream!’ But in fact these people may not have summoned the courage to really look within and see what passions lie there unexpressed. If you have sincerely looked and found that the status quo is not fulfilling, you are already making progress. If you are willing to engage in this conversation from a place of curiosity and not self-pity, you will get somewhere.

#2 – The choice is waiting for you.

A 20 year-old Hunter S. Thompson wrote a letter to a friend offering advice on this topic. In the gendered parlance of the time (1957), his advice is as follows:

“A man who procrastinates in his CHOOSING will inevitably have his choice made for him by circumstance. So if you now number yourself among the disenchanted, then you have no choice but to accept things as they are, or to seriously seek something else. But beware of looking for goals: look for a way of life. Decide how you want to live and then see what you can do to make a living WITHIN that way of life. But you say, “I don’t know where to look; I don’t know what to look for.”

“And there’s the crux. Is it worth giving up what I have to look for something better? I don’t know—is it? Who can make that decision but you? But even by DECIDING TO LOOK, you go a long way toward making the choice.”

What I love about this is how true it is. If you don’t choose, other people will choose for you. What you are looking for isn’t just a job or a goal, it really does rise to the level of being ‘a way of life.’ In fact, you already have a way of life – you are living it right now. Look at your last few days and weeks and months. That is your way of life. So how about it? Is it what you want?

When we asked the audience after the Seattle Sum and Substance how fulfilled they were at work the average was 7 on a scale of 10. In reading the comments, 7 isn’t bad. There is nothing actively wrong there, but there is a quiet suspicion that more is possible.

Here is what one 7 said:

“I love my company and I have a lot of autonomy and the company encourages creativity and side projects. However, it feels very routine and I just work in “marketing” with a lot of large corporations. I’m certainly not making a big impact in the world at all with what I’m doing.”

Compare that to a couple of people who were 10’s:

“I’m challenged, productive, making a difference, working with smart, kind, innovative, fun people.”

“My work process and outcomes are in alignment with my values and integrity. I am able to leverage and utilize my greatest gifts to better the forward
progress of others.”

A 7 and a 10 sound different don’t they? There is a clarity and confidence in a 10 that is not there in a 7. There is also clarity as you move down the
fulfillment scale.

Here is what one 5 said:

“I believe in the mission and the job provides stability, but I don’t feel valued or challenged.”

And here is a 3

“I don’t believe the work that I’m doing is helping others.”

Wherever you are on the fulfillment scale, you are the only one that can decide to look for something more. I’m guessing that, since you are reading this blog, you may have already made that choice.

#3 – Trust the tug

I’m willing to wager that at least one of the people I talked with during intermission in Seattle who just could not figure out what she might find fulfilling, actually had a very clear idea that she dismissed again and again because it just felt too risky. What stops so many people is that they a tug from their heart telling them they have a passion for something, and then they discard, deny or ignore it because they can’t see how it could ever become a real, paying job. This is fulfillment’s kiss of death.

In 2009, Steve Jobs gave the commencement address at Stanford. The whole thing is amazing to watch, but about 5 minutes in he says this:

“You can’t connect the dots looking forward. You can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something, your gut, destiny, life, karma whatever – because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path. And that will make all the difference.”

For him, it meant dropping out of college so he didn’t have to take required classes he wasn’t interested in. Instead he dropped into classes he was interested in, and found himself in a calligraphy class. Years later, that class would have a profound impact on the world as he insisted on building different typefaces into the original Macintosh word processor. Looking back in all lines up, but while in the calligraphy class, Mr. Jobs had no idea whether there would ever be a practical application for what he was learning. He just looked at the class list that semester and felt a tug toward calligraphy.

I’m not suggesting that you throw caution to the wind and dive headfirst into the unknown. But I am suggesting that you trust the tug when you feel it.

As David Whyte observes:

“Each step taken opens up the next step and the next.”

#4 Try Stuff

The answer to that classic question about what you would do if you had all the money in the world is not, in fact, laying on a beach.

As Paul Graham, the founder of Y Combinator, the most effective startup accelerator in the world (in dollar terms at least) wrote in a great blog about how to do what you love:

“Unproductive pleasures pall eventually. After a while you get tired of lying on the beach. If you want to stay happy, you have to do something.”

The true answer to what you would do if you didn’t have to work is probably what you already do when you’re not working. What are your hobbies? What do you do in your free time? Even if you just do more work, what work are you willing to do in your time out of the office? If you are working for a company that literally demands every second of your conscious attention (ahem – Amazon), what is it you miss most that you can’t do?

One of the best moments of the Paul Graham blog is when he offers a test for us to use in finding out for sure what we would love to do: Always produce. I’ll let him elaborate:

“For example, if you have a day job you don’t take seriously because you plan to be a novelist, are you producing? Are you writing pages of fiction, however bad? As long as you’re producing, you’ll know you’re not merely using the hazy vision of the grand novel you plan to write one day as an opiate. The view of it will be obstructed by the all too palpably flawed one you’re actually writing.

“Always produce” is also a heuristic for finding the work you love. If you subject yourself to that constraint, it will automatically push you away from things you think you’re supposed to work on, toward things you actually like. “Always produce” will discover your life’s work the way water, with the aid of gravity, finds the hole in your roof.

Of course, figuring out what you like to work on doesn’t mean you get to work on it. That’s a separate question. And if you’re ambitious you have to keep them separate: you have to make a conscious effort to keep your ideas about what you want from being contaminated by what seems possible.”

So even if you have no idea at all what you like or what you might want to do, pick something, anything and find a way to try it out for real.

So there you have it. These are some thoughts after the first Sum and Substance event. I hope it has been helpful.

Go forth and do great work. We’d love it if you would keep us posted on your progress (link to story submission).

Sum and Substance

Sources and More reading:

  • Steve Jobs’ 2009 Stanford Commencement Address
  • Paul Graham Founder of Y-Combinator’s excellent blog.
  • The Three Marriages, summarized by Maria Popova over at Brain Pickings.
  • A 20 Year-old Hunter S. Thompson had some wonderful thoughts on the subject (again courtesy of Brain Pickings).

Fortunately, the UK’s School of Life has published a book on the topic called , and even more fortunately, they have also made a very thorough video summarizing its six core ideas. To wit:

  • Being confused about career choice is perfectly normal
  • Know yourself
  • Think a lot
  • Try something
  • Reflect on what makes people unhappy
  • Be confident

You may find more advice and inspiration from our storyteller’s videos, which are all available at our YouTube Channel.

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