How I Built a Portfolio Career

Being an entrepreneur wasn’t the plan!

I worked as a teacher for ten years, in a fantastic school.  As teaching conditions go, mine were the best.  But something was off with where I found myself.  I studied more, worked on new initiatives in school, but there was a sense of fulfilment lacking. 

Year One

I took a career break, began to apply for other jobs, hoping my teaching experience would stand to me.  Jobs didn’t come so I worked as a substitute teacher in a different school.  Again, I was lucky.  The conditions here were great.  I could have stayed.  But I knew that whatever I found lacking in the last school would eventually catch up with me here.

I gave notice on my apartment, got a new passport and booked a ticket to Morocco just before Christmas, arrived in southern India in February, flew out of Kashmir, next to Pakistan in July, into Turkey but there was a coup against the government that evening, so I got a connection to London.  When I arrived in London, I stayed for a month. 

I asked everyone I knew to connect me with people in London.  I wanted to have conversations with people who could inspire me.  Who could shape and change my worldview?  If I, in my early 30s, am to change my career, how can I pivot into it with the skill set I already have?    

Year Two

I arrived back in Ireland nine months after I left.  I extended my career break and I applied for more jobs that I didn’t get.  I took what I could do – teach children and teach yoga.  As it was coming into Autumn, I looked up evening courses and found a few that were funded by the local authority.  At one, I sat next to a principal of a school for children with profound special needs.  We got on, she asked could I cover three days the following week.  I contacted the local authority and asked if there was funding to teach yoga, which led to an eight-week contract.

Working with children with special needs requires a different skill set.  It was a mirror.  If I was off, they picked up on it.  I had been studying mindfulness for a few years but this was where I began to practice present moment living for an extended period of time.  Aware that the needs of the children in my care could change at any moment.  I could be anxious about this or I reframe how I went into the classroom.  

Around the same time, I started an eight-month diploma in personal and professional coaching.  I was considering a psychology degree through the Open University but wasn’t ready to commit.  On my travels, a conversation I had with someone I spent a week travelling with sowed the seed of the value of coaching and mindset.   

For that year, I taught yoga, subbed in the school, trained as a coach, volunteered with a Book Festival and began to read more. 

The weekend of the coaching graduation was in a hotel in Portlaoise.  That afternoon, a conversation with one of the trainers sowed the seed that coaching could help the parents of the children I worked with.  The following week, I began to toy with the idea.  Could it?  How? 

Year Three

I extended my career break once again.  Someone told me about a social enterprise programme called BNest.  I applied with a very vague idea about coaching and mindfulness.  I interviewed and got in.  I continued teaching 3 days a week, I taught yoga, helped organise a book festival, and I found my first coaching client.  Over the course of the BNest programme I tested ideas and held focus groups.  Six months later, I launched ODODO.  It was an advocacy training programme using mindfulness and coaching for parents of children with special needs.  There was huge fanfare around the launch, the local press came, I felt like a fraud, standing there, I was talking to people about this business I had launched but I still had no actual product. 

After the launch, I froze.  For three months, I drew up and scrapped many iterations of what I was offering.  I had left this programme with the concept of a business, a website and no product. 

I found more coaching clients, I honed my skills.  I came across a course in the University of Oxford Mindfulness Centre called Mindfulness Based Cognitive Therapy.  I was intrigued.  I applied to do the first two modules of their foundational programme the following October.  That summer, I worked with a child in her home as part of the July Provision programme, she had many medical needs, needing round-the-clock care.  As I spoke with the parents, seeds of doubt about what I was offering crept in.  I asked them if they hypothetically would be interested in what I offered.  They said yes and no.  They shared their fight for everything their daughter had.  The care, funding for special furniture, wheelchair etc.  What I was hoping to offer wasn’t clear enough.  And, I realised that I had no real idea what they needed.    

Year Four

I decided to resign from my position in Dublin.  I entered year four and I subbed more.  I began to offer training courses to teachers on communication skills.  Something struck.  They were responsive.  I worked in Portugal for two weeks as a yoga and mindfulness teacher with an athletics team.  Later that year, I completed the first two modules of MBCT.  I connected with everyone on the training on a level I never felt before.  This is something I could feel it.  I swapped contact details.  Began to build friendships with people from around the world, connected by this powerful programme.  I came home, I bought the books and immersed myself in the training.  I started another business course.  On week 4, I realised that the woman giving the course was winging it.  She was teaching us how to grow a business, yet she never grew one.  She quoted from books that I had already read.  Over lunch I told her about a podcast I listened to it, the next week, that was her lesson.  I began to realise that the doubt I had in myself was holding me back.  I didn’t need to do another course, talk myself around things, I needed to start. 

I approached different organisations, ones for carer support, autism, Down Syndrome.  I arrived and gave a talk.  Told people what I knew.  Gave a talk on coaching skills and mindfulness.  I could feel the sweat droplets form.  I focussed on the disinterested in the crowd.  I did this for four months.  Driving around with my laptop and borrowed projector.  I got better.  I honed the skill of public speaking.  I engaged with people better, I met them where they were.  People began to come up to me and ask questions.  And some came to me for coaching.  Yet I was still holding tight onto this version of ODODO that I wanted.  On this circuit, my facilitation skills improved.  Standing and working with a live audience was a deep dive into figuring out why I felt insecure. 

I brought the face-to-face courses for teachers online, I sold more than I expected.  I continued the MBCT training, I put the money I made into the business.  I got by with frugality. 

Then the pandemic happened.  Things were on the ascent, and they were all cancelled.  I tried to get things online, but schools were closed, children needed care, the world was in chaos.  And I was stuck.

Year Five to Now

The start of the pandemic, I saw what I had built steadily over the years slip through my fingers like sand.  The course for teachers sold out, but that was only July.  Things moved online.  But most of my work was gone. 

Lost, feeling the fear and the spiral of doubt kick in, I began to write.  I wrote to companies and offered copywriting services.  Some responded, small jobs came in.  I hired a coach of my own.  I planned.  I joined online communities that had sprung up.  I met more people like me.  People who had designed their career.  I asked them if there was one place or person, they could send me to, to do it.  I found a mentor with Jessica Teal, she used to work with Obama in the White House.  I got this because I asked someone for help.  We worked together for three months.  She introduced me to two people, one turned out to align with my skillset and offerings. 

The best ideas come not from behind a computer, but from being out there in the world.  Talking to people, engaging with them, making friends, and not taking yourself too seriously.  And things take time. 

I started a newsletter, it was a test, to see if people engaged with my writing.  I sent it for 30 consecutive weeks.  I pivoted once again, I renamed it, I launched it with more intentionality.  Earlier this year, I started receiving emails from people who recommended me to others.  This was exciting and I also felt like a fraud.  What if they discover I’m no good? I thought.  I heard a podcast with Tim Ferris and Richard Schwartz on Internal Family Systems therapy.  It resonated, I went online and found a psychotherapist in the UK with the three levels of training complete.  I worked with these parts of me that stood in my way.  I detached more and more from the insecurity that held me back.

I closed ODODO, I realised that there was a part of me who created ODODO as I was too insecure to launch myself as a person with value to offer.  I hid behind the brand, and the brand didn’t take off because I was still unable to step forward and own what I was good at. 

I completed my training with MBCT and began my apprenticeships.  I learned to manage my time better and check-in with my motivation.  This was a learning curve on its own.  There’s no one to tell you what to do. 


The passive income from the online courses let me continue earning money after the real work was done.  People who have taken the courses have introduced me to people they think I’d work well with.  Again, this is an ask I say out loud.  Do you know someone who would be interested in talking with me.  And this isn’t about money.  This is about making connections with people who align with what do, chances are I’ll align with their work and from new friendships, who knows how we inspire each other. 

I’ve realised that each different project and experience has benefitted the others.  Different types of work also mean different income streams.

I am a creative who wears many hats, and I am not reliant on one client to fund my business.  At the start, I put all my eggs in one basket and when it did not work, it paralysed me.  I didn’t know this path of work existed when I started out on it.  It found me through my effort, my ability to pivot and the mindfulness training I have been lucky to practice and teach simultaneously.  I found how I can thrive via this work.  I have a workday, but my work is a part of my life.  I’ve ended up with a portfolio career.  A pie with many different slices, income coming from different people, companies and places.  I have a part-time job, I freelance and I create content such as articles, newsletters and courses.  My job is not based on one set of skills.

There have been many days where I have wondered if I should throw in the towel and get a “real-job” because this is all I was seeing around me.  Then I came across others via social media and newsletters.  I reached out, connected with some.

Right now, there are a lot of people online offering get rich quick schemes.  The wellbeing industry is worth a lot of money.  Retrain as a coach – launch a €10,000 a month business – etc. 

This doesn’t happen.  Nothing comes easily and why would you want it to?  The pleasure of life is in how we experience life.  And the journey to get here has been a deep deep dive into understanding myself.   

This lifestyle works for me.  It won’t work for everyone.   Just because you launch something doesn’t mean that it will take off over-night.  A lot of energy goes into the projects I work on.  I am only accountable to myself, otherwise I won’t get paid.  It is up to me to market and promote who I am.  I have worked a lot on this.  There were stories I had heard about myself in the past that had knocked a lot out of me.  And thankfully, this journey has shown me blocks within me to understand myself better. 

In the coming months, I’m launching new offerings and new income streams.  I’m exploring new and different combinations and partnerships.  This is exciting, fun and challenging.  I love that I never know who I am going to meet.  Who is about to come into my life and change its trajectory without even realising.  And the kind of work you put into the world influences the clients you attract.  With a portfolio career, I got to carve out a path and design a life for myself.  I often don’t know if something will work until I try.  This is a reminder that there isn’t one way of working.  This year I started working with people in the tech space.  The innovation and vision that is coming together amazes me. 

Running a portfolio career is to manage a living, breathing organism.  It can be scary at times, it also gives back to you more than you ever thought possible.  It is also something that some people won’t understand.  That’s ok.  That’s their stuff to understand, not mine or yours to explain to them.

Bit-by-bit, I’ve figured it out.  And I am always learning – about myself, how I work, what I can do better, what I do well.  There is excitement in this.  It took me longer than I’d thought to appreciate the effort that I was putting into it.  I didn’t celebrate the small wins at the start, I do now. 


I’d love to know if you relate to this.  Do you have a portfolio career or work for yourself in a different way?  Even if we’re on different journeys, we do share a similar roadmap. You can connect with me here


Cath O’Brien is a creative coach, mindfulness facilitator, and workshop facilitator.  She works with clients 1:1.  Sign up for her newsletter Curiously Connected for weekly connections and updates on offerings.


Photo by Kimberly Farmer on Unsplash

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