4 questions that will lead you to work you’ll love (or: How I ended up at Xero)

Don’t want to read my whole TL;DR story? No worries, here are my four critical questions I recommend to anyone looking for work you’ll love:

  1. What’s the ultimate impact you want to have?
  2. What industry do you want to be a part of?
  3. What type of work you want to do?
  4. What kind of people you want to work with, in what kind of environment?

Read on if you want to hear how I worked through these before landing my job at Xero. Better yet, get your own dream job (or freelance work that you’ll love) by answering these questions for yourself!


After happily working for myself for over four years, some nagging voices started bugging me. “You’re not using all your gifts,” they said. And, “where is your team? Why do you insist on working alone?” And there was a lot of, “there’s something much bigger waiting for you, but you have to look for it.”

I knew I was ready for something different. And I couldn’t shake the feeling that I wanted a full-time job where someone else would be responsible for hustling my paycheck, and I could focus on doing My Work. But other voices tried to justify the status quo: “The way things are now, you can go hiking or surfing whenever you want!” Or, “what about your weird sleeping patterns? You’ll never be able to work regular hours.” Or the worst, “do you really want to commute over an hour a day EACH WAY from gorgeous Bolinas to an office in San Francisco?!”

These voices couldn’t prevent me from admitting the truth: that The Work I want to do is so much larger than anything I can accomplish myself. And that no matter how awesome my coaching and consulting clients were (and still are!), I was lonely. I wanted peers. People in the same boat. People all working toward the same goal. At some point (maybe several points!) in any entrepreneur’s life, there’s room for a period of gainful employment. As a break. Or as a way to learn a new skill, on someone else’s dime. Or even as a way to find your next collaborators. There are so many reasons to go back to working for someone else!

At some point I realized that the only way to prove whether or not I was cut out for a JOB job was to get one and see what happened. But it couldn’t be any old job. It had to be one that would actually give me the opportunity to really spread my wings in a way that working for myself didn’t.

So as I always do while on the verge of a massive life shift, I thought long and hard about what I was trying to achieve, and what Wild Success would look like. 

I came up with these four questions for myself, and anyone looking for — or looking to create! — a new job:

  1. What’s the ultimate impact you want to have?
  2. What industry do you want to be a part of?
  3. What type of work you want to do?
  4. What kind of people you want to work with, in what kind of environment?

As for how I approached the question of What’s the ultimate impact I wanted to have, this has been clear to me for more than half my life: the results of my work must support people in their efforts to make a living doing — and BEING — whatever it is that they love. And this time around, I knew I wanted to be working at a larger scale than one business or one entrepreneur at a time. (Not because I don’t think that working directly with one person isn’t powerful! I still believe this is The most powerful scale we can work at, but that’s a topic for a future post.) You can read — or listen — to more of my reasoning behind that here. Bottom line: there was no way I would consider any job that wasn’t related to supporting entrepreneurs and creative people in making a living.

What industry did I want to be a part of? That part was a bit trickier, but based upon my analysis of the various barriers to building a livelihood doing what you love, I knew it had to be related to MONEY. More specifically, how people relate to and/or access money to launch or grow their ventures. And I wanted to be part of the solution, not the problem, which eliminated jobs at traditional banks or venture capital firms or even some of the newfangled lending options like Amazon loans, since they so often perpetuate the challenges facing people’s ability to make a creative living… but I did consider crowdfunding companies and innovative lenders fair game. And I really struggled to think of anything beyond that.

Around this time I signed up with glassdoor (I don’t think it was all lowercase at the time, ha) and started using their job search features (searching keywords “finance” “lending” “small business” “crowdfunding” etc) to see what sorts of companies were posting jobs in those areas. I read up on what people were saying about them, and started following a few that looked interesting.

I noticed that Xero, a cloud accounting software company, had quite a few jobs listed, and this company got relatively high reviews from former and current employees. I’d heard about Xero through a consulting client that was using their software, and they really seemed to be changing the game in terms of making it easier for small businesses and nonprofits to see what’s going on with their financial details… a huge boon in terms of helping small businesses raise capital!

Though I did skim the jobs each had listed, I didn’t actually pay much attention to those yet because I didn’t want to cloud my thinking on the next question…

What type of work did I want to do? This was actually the hardest question of the four for me to answer. I’ve done a lot of different things, some of them more happily than others. I really wanted to continue coaching in some capacity, and I love love love teaching workshops and such… wouldn’t it be awesome to be doing some combo of writing and speaking and teaching workshops? Not a typical job description! And that’s the other reason why I didn’t want to look too closely at the job listings: I’ve rarely held jobs with “normal” job titles. As a result, I don’t always understand what the titles mean at first glance, but more importantly, I’d much rather meet with someone at a company I’m interested in, ask a bunch of questions about what they’re hoping to accomplish, and if I like what I’m hearing, show them that I’m the perfect person to serve in that role they hadn’t dreamed up yet 🙂

Meanwhile, I was talking to friends and colleagues about what they were seeing out in the world. Given my answers to these first three questions, what would they recommend for me? A friend who had recently left Apple suggeted I look into Apple U[niversity]. “Not that I’d recommend working there,” she said, “but the program is interesting, it’s voluntary leadership development for employees…”

This was super eye-opening for me. Until that conversation, I had no idea that big companies had entire educational departments, and that seemed like a great way for me to apply the skills I wanted to be using, in a company within my chosen industry.

Turned out Xero had a job opening in their education department. The person in this role would produce content for Xero U, their externally-facing training site, namely webinars, live videos, conference workshops. Now I really perked up. Of course I’d want to receive a regular paycheck to do essentially what I was already doing: producing content that would help small businesses spend less time worrying about where their money is going, and how they can most efficiently bring it in. And occasionally getting to go to conferences in interesting places to hang out with fascinating people and teach them a course or two.

I got a call back the very next business day after submitting my application. I don’t share this as a humble brag. I share this because I honestly believe that getting really clear on your answers to questions 1-3 will make you a shoe-in for whatever job you apply for, assuming you only apply for jobs that meet your criteria, and you can show that you’re qualified to do the work (and I realize the latter can be a significant barrier.) But you still need need to answer question 4 to make sure it’s a good fit.

What kind of people did I want to work with, and in what kind of environment? Super brilliant people who get stuff done and have a good time doing it, obviously! And it’s very important to me that I can bring my whole self to work, so there was no way I was going to consider a super stuffy office where nobody let their hair down. Or where they’d freak out if I went on a social justice or inclusivity rant at work, or let my personality show through at a speaking gig, for instance, or had a cry in the middle of a meeting (it happens!).

Since I care so much about the purpose of what I’m doing, I also wanted to find a place where people also saw meaning in their work, rather than just seeing their job as a paycheck. And as someone who has historically spent more social time with my colleagues than with anyone else, I hoped to surround myself with inspiring, inquisitive people who had lives and passions outside of work, too.

When my first interview (over Google Hangouts) seemed to be going well, and the role sounded like an excellent fit with the type of work I wanted to do, I started asking tough questions. “Look, I’m a bit of a goofball,” I said. “Is that going to fly at Xero?” The manager interviewing me started laughing. “I think you’d fit right in,” she said, and explained that #human is one of Xero’s values. What about my tendency to bring up power dynamics and instigate on behalf of those in less privileged positions? She wasn’t phased by the question, and added that #challenge is also on the list of values.

I won’t go into all the details other than to say that she told everyone later that the conversation felt more like I was interviewing her rather than the other way around, which seems fair: when someone is proposing that I commit most of my productive hours to them, damn straight I’ll ask them to prove that they’re worth it!

Round two interviews took place in Xero’s San Francisco office. Specifically, I was scheduled for three different interviews over an hour and a half. I’m sure I answered some questions, but mostly I remember grilling my would-be colleagues on why they were there, whether people felt comfortable being themselves, and the general office vibe. Turns out they too were excited to be supporting small businesses, and couldn’t believe their luck to be paid to do something they loved. They struck me as thoughtful, motivated, funny, and the kind of people I’d want to sit next to at a dinner party.

A couple hours passed and we were all still having a great chat, so they invited me to stay for lunch, which Xero caters for San Francisco employees every Thursday. While I’m sure the recruiter planned it that way, I hadn’t expected to fall in love with expansive views of the water and Bay Bridge from the rooftop deck over Vietnamese food…

What I didn’t know that day was that I’d eventually fall in love with colleagues from all departments over ping pong, board game night, kickball, conferences (Xerocons have been the most fun but we brought the party to others’ events as well), and countless hard-but-rewarding work projects. Or that I’d ultimately move with the company to the country where it began (New Zealand) with a new role on the Video and Media team, two different dreams come true.

When I finally left the Xero office that day, I did know that I had found a company, a role, and a community that met my expectations for the impact I wanted to have, the industry I wanted to be a part of, the type of work I wanted to do, the kinds of people I wanted to work with, in the kind of environment where I could thrive.

A few days later they made me an offer, which I accepted without hesitation.

Today is my two-year anniversary as a Xero employee, and I love being aboard this rocket ship along with a team of people who amplify each others’ efforts to support passionate entrepreneurs and small businesses, all over the world.


So that’s the story of my experience using four questions to find work I love. The hardest part by far was answering the questions honestly and completely, and the way I’ve written this piece I may have understated how challenging that step really is. But once I’d done that soul searching, the rest seemed to fall into place by itself.

Regarding those earlier nagging voices, some of them were right: my team was out there somewhere. The bigger work was waiting. But the worries were unfounded, if not ridiculously shortsighted given the amazing shifts that this job has allowed me to make in my life. To be fair, those worries came to me before I had the answers to my Four Questions. They stopped bothering me once I started visualizing my ideal conditions, and then searching for something that aligned with that vision.

I highly recommend this process if you ever find yourself dissatisfied with your current work situation and you’re ready for something different. Try it out and let me know how you go!


And once more,

Four critical questions I recommend to anyone looking for work you’ll love:

  1. What’s the ultimate impact you want to have?
  2. What industry do you want to be a part of?
  3. What type of work you want to do?
  4. What kind of people you want to work with, in what kind of environment?