Would You Rather Be …

Why Employment?

Since starting my journey into social entrepreneurship just over a year ago, I’ve given a lot of thought to the best ways software can make a difference to people’s lives. I explored the many ways that software is making a difference today. These cover broad categories like education, employment, healthcare and finance. They also cover narrower categories like refugees, homeless people, victims of trafficking and disabled people.


But what problems can be solved within employment that software can be leveraged to address? And what problems am I passionate about?

Prototyping Your Career

Last year I went to a talk by Dave Evans, a Professor at Stanford University. He led the design of Apple’s first mouse and co-founded the games company Electronic Arts. He came to London and gave a talk on “Designing Your Life”. This was based on his lecture series at Stanford, which is the most popular at the university. The essence of his talk was the idea of “prototyping” your career.

Connecting People to Explore Careers through Conversation

While I was on a walk in the early summer this year, I came up with the idea of building a platform to connect people who are interested in certain careers with other people doing those careers so they can have a conversation. They could pay to have these conversations. This means that anyone doing a job could get paid to talk about their job with someone else. And of course the platform would keep a cut so it could scale and be sustainable.


Deciding Between Two Careers

My first step was to get a pretty comprehensive list of careers that people can pursue in the UK. There are many websites that helped to form this list. I came up with about 400 careers.

Commonality Between Careers

In order to solve this problem, I needed to first figure out attributes that different careers have in common. As people made choices between pairs of careers, I could then get a signal on what attributes matter most to someone. That would then infer the careers that would suit them.

Qualities that Best Describe Careers

My goal though is to help people find careers that are most satisfying to them. And I wanted to think through the problem from first principles and come up with attributes that match really well to jobs. So I went through each of the 400 careers and tried to pick one word that best describes what each career is about and why someone might find it satisfying.

Crafting an Algorithm

The most complex part was figuring out what pairs of careers to show a person. Picking them at random would yield a weak signal, so they had to be selected intelligently based on their previous choices. Then as people answer the questions, it hones in on the qualities that they find most satisfying in a career.

Building Would You Rather Be

I built the model using the approach described above by carefully reading through the job descriptions for all 400 careers and mapping them into my model based on the qualities I defined.


Friends & Family

Once I had finished building the first version, I tested it with myself a few times and then with friends and family. This yielded a lot of useful learnings.

Target Market

Where to Find People

I then needed to test my product with people in my target market — ideally soon-to-be or recent graduates. To start with, I spent a day researching many possibilities for how I could reach these people. I looked at local universities, colleges and schools and got in touch with local people who run student groups and job clubs. I researched job fairs and got in touch with three big upcoming job fairs in London. And I researched a few careers advisors and coaches.

Finding a Way Into a London Job Fair

My best bet were the three big upcoming job fairs in London. I called each one and they all offered me the opportunity to exhibit there, but at a cost of at least £3,000. As I only needed about 6–8 user tests, I figured it wouldn’t be worth paying more than £300. So I tried negotiating and pitching myself as a hot new tech startup that would add value to their conference. Unfortunately it didn’t work.

Preparing For and Acting as a Careers Advisor for Two Days

But now I had about 3 working days to prepare and I had never been a careers advisor before! I went along to another exhibition for school leavers and sat in on a talk from a careers advisor there and took notes. I used the platform Fiverr to have a designer create a logo and business cards for me for £50.

Learnings about the Product

What Went Well

The app seemed to work well for about 70–80% of people. It tended to work best for people who were more self-aware and understood what they enjoyed. This is because the app is predicated on the person being able to make good choices on which careers they prefer. It yielded a good set of jobs for most people and almost always yielded more ideas than that person already had.

Food for Thought

Some small improvements that people voiced were that it was a little too long. And in some cases, people didn’t want to do either career, so they wanted a “neither” option. But that didn’t stop people from completing the app.

  • People (often students) may not want to pay for these
  • Some people doing certain careers, such as those in very busy jobs, may not have the time or incentive to have these conversations
  • There is a logistical cost to setup these conversations, although software may be able to help with this
  • It is quite a low income opportunity as the most I think I could keep per conversation is £5–10

Learnings about Myself

I’ve also learnt a few things about myself during this project. I realise that I really value working with other people in a team. Working on my own for a long period of time doesn’t suit me.

Next Steps

Immediate Next Steps

There are a couple of things I want to pursue with this project over the next couple of months or so.

Raising Money and Finding Cofounders

At some point I may also try and raise some funding. There is a scheme called SEIS whereby it is relatively easy to raise up to £150,000 from wealthy individuals as it is extremely tax efficient for them to invest. Raising money would then give me far more options to explore focusing on this fulltime and finding a cofounder or two to join me on the journey. Given what I have learnt about myself during this project, I think that is an important step for me to take if I want to take this project much further.

A Much Bigger Product Vision

There are a few more steps I can help solve to get people into a satisfying job. I’ve helped people identify the roles that may satisfy them, but I could then help them identify the ideal companies for them that have these open roles, help them get a job there and then help them flourish in that job.

Making Money

There are lots of ways to make money and build a scalable and sustainable business in this space too. We could charge applicants for some of these services, either up front or after they get a job (so tied to results). It could even be a % of their first paycheck. We could also charge employers for advertising jobs, recruitment fees, providing a mentoring service or helping their employees develop skills. And we could get referral fees for referring users to career and life coaches.

A Short Update on Past Projects

You may be wondering what has happened to the malaria chatbot and education web app.


Thanks for reading! If you’ve not tried the app yet, give it a go at www.wouldyouratherbe.com.



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