Getting outside your own head

What I learned from The Hot Seat about finding meaningful work

I have a tendency to overthink, sometimes to the point of paralysis. Over the last year I’ve thought, heavily, about how I can find more meaning and satisfaction in the work I do. And, as you might expect, a lot of that thinking got me precisely nowhere.

But getting outside of my own head by hearing other people’s perspectives has been life changing — or rather, ‘work changing’.

One of the useful experiences of the last few months was featuring on the Happy Startups Hot Seat, where community members offer questions, advice and ideas in response to a challenge.

My question to the Hot Seat group was a common one:

How to bridge the gap between work that pays the bills and work that gives life meaning?

The work I had done in marketing over the last year had left me drained and diminished — ‘emotionally dehydrated’, to borrow Bob Olmstead’s phase (see below). I was looking for a way forward from my muddle of ideas and limitations.

Four months on I’m much happier with the work I do. I’m contributing to projects I value and although my greater sense of ‘purpose’ is unresolved, I’m getting much more satisfaction from the process of exploration.

Here are some of the pieces of advice from the Hot Seat that have stuck with me:

1. Surviving, and then thriving

‘Have an in between gig to keep yourself funded but free, while you’re working on crafting your dream’. — Bob Olmstead

Bob Olmstead is a creative coach and has been through his own process of finding — and creating — work he loves.

He highlighted the need to stay ‘funded but free’ while chasing your ultimate goals, allowing the time and means to find work that feels more purposeful.

This is something I had discounted at first in my impatience to ‘get there’.

But the truth that I’ve realised over the last year is that the process of finding purposeful, satisfying work is often a long one. Allowing yourself time means you can enjoy the journey, rather than feeling pressed to just take the next thing.

When it comes to ‘thriving’ part, his advice was to go deep, to take the time to find out what you really need.

There is a lot of material out there promising shortcuts to finding your own sense of purpose. In my experience none of them last. The only road is the one you have to pave for yourself and it is hard work, but worth the effort.

2. Follow your curiosity

‘Follow your curiosity and be patient.’ — Carlos Saba

Carlos, Co-Founder of The Happy Startup School, emphasised the time it takes to find a clear sense of purpose and the importance of curiosity in the process. Finding your ‘purpose’ is a big task and it can feel very abstract, where following your curiosity is more playful and tangible.

Reflecting on Carlos’ comments some months later, this has proved to be good advice. Following my curiosity has started conversations and opened doors to new opportunities, even when the question of ‘purpose’ remained unclear.

My curiosity is what led me to start having conversations with others about meaningful work and this led to events and a blog. It’s a continuing process, but it has been an enjoyable one.

3. What would you do if money were no object?

‘What makes you tick, what makes your blood boil, what makes you jump out of bed in the morning?’ — Sean O’Leary

Sean O’Leary is an entrepreneur and advisor. He reminded me of Alan Watt’s speech about the traps we set ourselves when we chase money as a primary objective.

What do you desire? — Alan Watts

Although it can seem like the bigger salary is the better option, if it means you spend your days doing work you hate it will never be worth it. Instead, focusing on the work you love doing over time will bring satisfaction and, ultimately, expertise. And you can charge for expertise.

‘If you say that getting the money is the most important thing, you will spend your life completely wasting your time. You’ll be doing things you don’t like doing in order to go on living, that is to go on doing things you don’t like doing…’ — Alan Watts

4. The answer is not in your head

‘Feel what makes you proud, and go and do those things in the service of others’ — David Papa

Some of the wisest advice came from David Papa, a coach and facilitator. He recorded a video for me in response to my Hot Seat questions and gave three pieces of advice, which have proved to be pretty much spot on this for year.

David’s advice was:

  • Focus on feelings — the tasks and work that feels good, particularly feelings of pride and excitement.
  • Never work alone — find collaborators with different strengths and fears to your own.
  • Work in the service of others — be responsive to other people’s (and other companies’) needs.

As a natural over-thinker this focus on feelings let me side-step a whole tangle of mental chaos.

In the months since I’ve made a few more gut-based decisions and am learning to pay more attention to the way work feels. I’ve also found that others have been more open to collaboration than I might expect.

Getting outside my own head to absorb different perspectives has been both inspiring and reassuring. Feelings of deep dissatisfaction with work are a prompt to take action, and to start exploring. Most importantly, I’ve learnt that it’s a gradual process. Radical leaps won’t necessarily get you there, but curiosity and attentiveness to your own experiences will help you move in the right direction.

If you’re feeling diminished by your work life, start some new conversations. Speak to someone different. Get some perspectives from others and begin to stretch your curiosity a little.

I started the year with the goal to have conversations with 100 people about purposeful work (currently 85 and counting). Read more about these conversations at