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Don’t start with the problem. Start with the people.

How to use a service-first mentality to choose your next project.

I’m in between big projects right now and trying to decide: what’s next?

First, I explored a super-nerdy approach to choosing my next project:

My Decision Criteria spreadsheet from How To Decide: Criteria-Based Decision Making.

It was overkill. Overthinking at its best.

But I’m glad I did it. It forced me to make a list of projects and ideas I’m excited about and rank them against personally meaningful soul criteria — values, joy, purpose — alongside more practical survival metrics, like income, earning potential, timing, and skills.

It was painful to plot out cell by cell, but felt satisfying in a self-indulgent kind of way. And it served as an important reminder in a time of transition: there’s a ton of exciting projects I could work on.

On the other hand, looking at the heat-mapped spreadsheet above makes me queasy and reminds me: we’re a heady species. How often and easily we get stuck in our own introspection.

And if I’ve learned anything, sometimes the best way out is to redirect the focus off ourselves and toward serving another human being.

Who do you want to serve?

After reading my nerdy decision criteria article, author and designer Monika Kanokova responded with an excerpt from her book Work Trips and Road Trips:

“When you know who the people are you want to serve with your work…it will be easier to decide how you want to allocate your time and your resources. Knowing who shall benefit from your work will automatically make it easier to decide what sort of work or volunteering activities you might want to pursue.”

This echoed a passage from another book, Designing Your Life:

“Don’t start with the problem, start with the people. Start with empathy.”

While I touched on who I’d like to serve with my decision criteria “purpose,” I wasn’t specific about “who shall benefit” from my purpose-related work.

The next day, I brainstormed 10 communities or people I have served or would like to serve with my work, including past or current projects or ideas:

  1. Unhappy corporate professionals / hopeful career changers seeking guidance. [My work at Escape, freelance workshops and talks]
  2. Americans who want to travel more consciously, less like a consumer. [Tales of Iceland book]
  3. Writers / creatives / introverts seeking quiet, contemplative space to do their work around the world. [Creator Caves / Writing Cabins idea]
  4. Deliberate journeyers / wanderers seeking their place in the world. [My TEDx, GiveLiveExplore blog]
  5. People who’d like reminders to live deliberately and encouragement to chisel away at their goals. [100 Day Mission, GiveLiveExplore]
  6. Early 20s career direction seekers. [GiveLiveExplore, Escape]
  7. 30s/ 40s/ 50s /middle-aged women professionals seeking more confidence in career next steps (don’t laugh, I’m learning it’s a sweet spot of mine.) [GiveLiveExplore, Escape]
  8. Obsessive travelers who are mindful of their impact on planet. [Not currently serving.]
  9. People seeking a richer relationship to the natural world. [Nature is My Church article.]
  10. Non-writers trying to break into writing. [This is how you write article]

Not so surprising, but the people I’d most like to serve are either those like me today, or a version of myself from the past (nix middle-aged women).

But this exercise posed new questions: What about earning an income? And where does personal pleasure and joy fit in?

“Make Something People Want”

You could serve a community or help solve a problem for a specific group — but will it pay the bills?

On one hand, maybe not every project should be expected to. I’ve categorized some projects Soul Work and others Survival Work to account for that reality. On the other hand, if I’ve learned anything about business in a capitalist society, on the flip side of service usually lives opportunity.

There seem to be two approaches to starting a successful business:

  1. Scratch your own itch.
  2. Create something of value for someone else.

In other words, serve someone. Even if that first someone is yourself.

Photo: Matt Biddulph

In his fantastic essay Be Good, startup whisperer Paul Graham gives founders at Y-Combinator two pieces of advice:

  1. “Make something people want.”
  2. “Don’t worry too much about the business model, at least at first.”
“A couple weeks ago I realized that if you put those two ideas together, you get something surprising…What you’ve got is a description of a charity.”

Graham lists both Craigslist and Google as examples of successful startups that looked more like nonprofits in the early years. By focusing on solving a real problem and tirelessly serving a group of people they cared about, both became successful businesses.

Service drove them. The money followed.

“Do whatever’s best for your users. You can hold onto this like a rope in a hurricane, and it will save you if anything can. Follow it and it will take you through everything you need to do.” –Paul Graham

Purpose Needs Pleasure

A few days later, I went to the hospital to diagnose a crippling pain in my right foot. The doctor and I got into some small talk and he asked what I did for work.

My first impulse was to send him my What do you do? post. But then I answered: “I write, speak, and facilitate workshops.”

“So you’re on your feet a lot?”

“Not exactly. I don’t facilitate every day. I’m actually in a transitionary place right now…” I could feel this going down a rabbit hole, so I cut it short. “I do workshops once a month or so.”

Head down, poking at my foot, he asked “What kind of workshops?”

“Career change. I help people escape unfulfilling corporate jobs and find more fulfilling work.”

The doctor looked up, his eyes widened. He leaned in and smirked.

“So, could you help me?”

Before I could answer, the doctor leaned back and called across the hall.

“Diana, come over here!”

My right foot still stiff and elevated on the bed while my left dangled below. I waited for the other doctor to enter.

“Listen to this. Matt runs workshops to help people leave jobs they don’t like.”

The other doctor perked up. “So if I went to your website right now, could I book myself on a course?”

“Well, it’s complicated. I recently left…” I paused. “Go to my site and shoot me an email. I’ll sort you out.”

What’s fascinating is that the doctor has what many unfulfilled professionals I meet don’t: built-in purpose. Purpose is at the heart of a doctor’s work. Especially if they’re patient facing, doctors touch purpose every single day. They stare purpose in the face. And yet the giddiness of those two doctors was palpable.

This is a big generalization that I’m sure doesn’t apply to everyone, but the most common source of discontent I’ve seen with the doctors is lack of creativity, play, or pleasure in their work. In between the helping and healing, they get tangled up with politics, beuararcacy and minutia. Suddenly, the job doesn’t excite them any more.

Which begs the question: what if you feel a deep sense of purpose in serving people or specific cause with your work, but the work makes you miserable? Or at the very least, what if you don’t find pleasure in what you do?

It’s a question I’ve wrestled with as well. Last year I wrote about my struggle to juggle the rewarding transformative work I had the honor to do at Escape and the deep emotional toll it took on me:

“I’m having a hard time with this. I’m absorbing everyone’s challenges, their stuckness, their pain, their suffering.”

Career change, identity, purpose, meaning — this is heavy stuff. Even today when leading workshops, I need to remind myself to bring three core intentions to my work. The first of which is “Have fun!”

Intentions to myself.

In other words, I need to remind myself to take pleasure in the deeply purposeful work I do.

My conversation with the doctors and my work at Escape reminds me of the core theme in the book Happiness by Design. Author Paul Dolan found that it’s the combination of purpose and pleasure over time which produces happiness in the long-term:

“To be truly happy, then you need to feel both pleasure and purpose. You can be just as happy or sad as I am but with very different combinations of pleasure and purpose. And you may require each to different degrees at different times. But you do need to feel both.”

So start with empathy — the people you’d like to serve.

But like they say on the airplanes: “Put on your oxygen mask before assisting others.”

Don’t forget to empathize with your future self.