“Don’t start with the problem, start with the people. Start with empathy.” –Bill Burnett & Dave Evans, Designing Your Life

Last week I explored a super-nerdy approach to choosing my next project(s).

This week, I’d like to touch on another decision-making tool, one based less on personal drivers like interests, values and excitement, and more on the external factor of service.

Who do you want to serve?

This question came courtesy Monika in Vienna, who responded to my post 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 – which doesn’t even have to be just one specific group, it can be multiple – 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.”

I touched on Monika’s question “who do you want to serve?” with one of my decision criteria last week: purpose. But I wasn’t specific about whom might benefit from purpose-related work. I brainstormed 10 communities or types of people I have served or would like to serve with my work:

  • Unhappy corporate professionals / hopeful career changers seeking direction / guidance.
  • Americans who want to travel more mindfully, less like a consumer.
  • Writers / creatives / introverts seeking quiet, contemplative space to do their work around the world.
  • Deliberate journeyers / wanderers seeking their place in the world.
  • People who’d like reminders to live deliberately and mindfully in the everyday.
  • Early 20s career direction seekers.
  • 30s/ 40s/ 50s /middle-aged women seeking more confidence in career next steps (don’t laugh, I’m learning this is a sweet spot of mine…)
  • Travelers who want to keep traveling but mindful of their impact on planet.
  • People seeking a richer relationship to the natural world.
  • Non-writers trying to break into writing.

Maybe not surprising, but the people I’d most like to serve are either people like me today, or a version of myself from the past (especially middle-aged women…). I also noticed that almost every group mapped to one or several of my values and/or skills I had developed over the years.

Are purpose and service the highest value decision criteria? What about making money? Excitement, pleasure and joy?

Focusing solely on service, I worry two important decision criteria could get lost in the mix: bill-paying survival work and pleasure-filled soul work.

“Make Something People Want”

I 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 pay the bills. 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.

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

  1. “Make something people want” and
  2. “Don’t worry too much about the business model, at least at first.”
Photo: Matt Biddulph


“A couple weeks ago I realized that if you put those two ideas together, you get something surprising. Make something people want. Don’t worry too much about making money. 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.

Purpose needs Pleasure

A few days ago I went to the hospital to diagnose a 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 to my “What do you do?” post…  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. Actually I’m 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.”

“What kind of workshops?”

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

The doctor’s eyes widened. He leaned in. “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 laid straight 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 escape the jobs they don’t like.”

“So if I went to your site right now, I’d be able to book myself on a course?”

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


What’s fascinating to me is that the doctor has what most other 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 found with the unfulfilled doctors I’ve met is lack pleasure in their work. It doesn’t excite them any more.

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

This is a question I’ve personally wrestled with. 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, purpose, meaning – this is heavy stuff! Even today I need to remind myself to bring three core intentions to my work. The first of which is “Have fun!”

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.”

All in all, I think service is a great leading criteria for new projects. The money may follow. It also may not.

But service and purpose with no pleasure? I’ll see you on the next career change workshop.

Over to you – who might you serve with your work?

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