From High School Teacher to Glasto DJ, Comedian and Uke-trepreneur — my decade in drawings.

Sarah Weiler
16 min readJan 6, 2020


‘Most people over-estimate what can happen in a year and under-estimate what can happen in 10.’ — Bill Gates.

How to summarise a decade? There are so many different lenses to look through: where we’ve lived, how we were feeling each year, our changing support network, our values, our hopes, our challenges.

For me it felt important to track my transition from full-time school teacher to self-employed creative entrepreneur. I now proudly lead a very varied, multi-project life, where I earn money from doing things I love and from ideas and concepts I have created, but this was not the case 10 years ago…

I decided to get creative and draw my decade; placing the projects and employment that made up my life into these four different categories:

Level 1 is ‘working for someone else’.

Level 2 is for ‘projects, hobbies and ideas’ — these are anything that took up my time but there was no money exchanged at this point: seedlings of ideas or pure fun.

Level 3 is for ‘side-hustles’ — this is when these projects started to bring in some money.

In the later part of the decade I also placed ‘significant events’ here — projects that didn’t necessarily bring in money, but seemed to be worthy of a higher place than ‘idea’.

Level 4: I’ve called this section ‘good money’ — this is where I am earning regular and consistent income from something I have instigated or created.

Below are the sketches and a story of what was happening each year. For those of you thinking of transitioning into a more Carousel lifestyle, I hope this is useful. And for all you multi-potentialites, I hope you find parts of this up and down journey that resonate.

Feel free to just look at the drawings, or dive into the whole thing. I hope you enjoy it!

With love,

Sarah x


At the start of the decade I was teaching Spanish and German in a secondary school in Uxbridge as part of the Teach First programme.

Teaching was all consuming, but I did start writing comedy songs about my students, which was very cathartic.

I also formed an acoustic duo with my colleague Rhiannon and we performed her incredible songs at open mics and festivals.

I had not yet considered setting up my own business, I only knew that the energy levels required to be a full time teacher were not compatible with how I operated. I needed to feel free!

One rainy January following Latino beats at a Zumba class (I think it was this track that clinched it), my housemate and I decided to quit in the summer term and go to South America.

I feel very grateful for all I learned in teaching: how to plan sessions, create resources, hold space, time manage, understand motivation, humans’ needs, (any group of adults I work with now is a complete breeze in comparison), but GOD was I glad to leave!

Lived in: South Ealing

Travelled to: Brazil

Best moment: Playing piano requests in Crispin’s Wine Bar in Ealing with a full bar singing.

Hardest moment: Every lesson with 8Q


I travelled with Loups and Sku (two teacher friends) to Argentina, Ecuador and Colombia until Christmas. We saw penguins, climbed mountains and constantly felt guilty that we should be working — (it took a long time to settle out of the pace of teaching and just enjoy travelling.)

Then from Jan-March I worked for the Argentine version of Teach First — Enseña por Argentina. I had the best international house-share in Buenos Aires, and it was there I first learned the ukulele!

I returned to London and immediately got a job at HEAPS (Higher Education Access programme for state schools) organising a summer festival for the 6th formers. I LOVED it and felt so free living in London and not being a teacher! Evenings to myself?! Arrive at work at 9am? I couldn’t believe it…

I got approached by an old Teach First friend to come to Vienna until Christmas to help out with Teach for Austria. I also applied for a permanent job with HEAPS. I got offered both. My boss at Teach First said, ‘make a list of the pros and cons and then go with your gut.’ I chose Vienna. (Because — Julie.)

Lived in: Buenos Aires, Haggerston, Whitechapel

Travelled to: Argentina, Colombia, Ecuador, Uruguay, Spain, Canada (wow!)

Significant Mentor: Kimberly at ExA who helped me understand my strengths.

Best moment: Torres del Paine trek in Patagonia.

Hardest moment: Navigating a long distance relationship while travelling


This was an amazing year of huge learnings and professional growth.

After a few weeks in Vienna I was asked to extend my stay for the year, set-up the entire training programme with one other staff member and coach 24 Austrian teachers in their first year of teaching. I travelled regularly to Salzburg for my Julie Andrews fix — it was a dream come true.

The blank canvas of a start-up was both liberating and overwhelming, but I loved gaining insight into a company in its first year, and all the leadership challenges that came with that. My interim boss, the COO, taught me so much about Leadership models, MBTI and human behaviour, which I have no doubt have influenced what I am doing today.

The climate was tough, so I wrote a song on the uke and suggested we sang it as a staff. Although initially met with resistance; the uke, and singing together, became a huge lifeline for our company culture that first year, and without knowing it Power of Uke was being born.

I also had the luxury of living on my own in a gorgeous Viennese apartment. I spent many evenings going through John Williams’ and Selina Barker’s Ignition programme, and working out for the first time what I actually loved doing, and entertaining the idea that I could earn money from PLAY!

I wrote a list of 24 things that made me feel alive. In 2013 only six of them were in my life. I’ve revisited it every year and now I think almost all of them are in my day-to-day. It didn’t have to happen straight away as paid work, but bringing these joys into my life even in a small way — over time they morphed into much bigger projects.

Lived in: Vienna

Travelled to: Bratislava, Prague, Budapest, Argentina (went back to visit),Seville

Best moment: Spending the last night of the Summer Akademie at the Sound of Music house!

Hardest moment: Really struggling the first term with my role, the team, the language and my flatmates, before I moved.


While I was in Vienna, I applied to the Winston Churchill Memorial Trust for the education grant, and got it!

I wanted to revolutionise language teaching and see young people learn Spanish through authentic culture.

I spent 4 months travelling around Colombia, interviewing musicians and collecting sounds and styles. On my return I created ‘Pasaporte Cultural’, an immersive language and music project for schools with two Colombian musicians I met in London. Later that year I incorporated Pasaporte Cultural LTD — I had my own company!

In January 2014 I made the decision to no longer be in full time employment. I took a maternity cover teaching music and drama at a Harris Academy, trained to be an assessor for Teach First and tutored. I put one day aside to focus on my ‘social enterprise’ but I was a bit lost and overwhelmed with all the ideas, and the exhaustion of constantly changing jobs. There was a lot of guilt about how I should be spending my time…

Also, while I was in Colombia, my staff at Teach for Austria had sent me a video of them all playing the ukulele together at a staff meeting — an image came to me at that moment of doing corporate uke workshops. I started running uke meet ups in Brixton to practise teaching it to groups.

In June 2014 I did John Williams’ 30 Day Challenge — writing 30 minutes of comedy in 30 days and putting on a comedy show. We sold out a top room of a pub and the landlord asked us if we wanted to run it regularly. My friend Rose was at the bar with me and said, ‘I’ll run it with you! and Rye Laughs was born!

In July I drew a line under teaching — I had thought that maybe I’d enjoy it more if I was teaching music, but it was still really exhausting. But I am so grateful that I learned how to teach big groups the guitar as I learned all the pedagogy I needed for Power of Uke…

2014 was a big year for ideas. It was like I had come back and finally had permission to create everything I wanted to — I bursted out of myself that year!

Lived in: Colombia, Streatham Hill, Kennington

Travelled to: Colombia

Best moment(s): Partying at the Carnival de Blancos y Negros in Pasto + completing the 30 Day Challenge

Hardest moment: Teaching at Harris Academy — knowing I was done, and still having a month to go.


Another year of abundant creation! And letting go…

In October ’14 a friend and I met on a Sunday to play music and do creative things — an excited conversation ended up with us posting on FB: ‘who wants to come to the countryside and be creative for the weekend?’ We found a venue and filled all the places in 48 hours. This was the start of a BIG adventure, running four Creative Retreats over two years, helping people reconnect with their creativity in the beautiful countryside.

I continued to work at Teach First and tutor, and found my ideal teaching age with nursery and Early Years during the summer term.

Rye Laughs had its first few gigs on a Pay What You Want basis. We gathered good crowds and changed venue twice. I continued to write songs and got through to the semi finals of the Funny Women Awards.

After a huge initial take up with Pasaporte Cultural in the summer, I got NO bookings for the Autumn term. It felt like a real slog to get sales. I applied for an Innovation Award and didn’t get it. I started to wonder if this was the right project for me, or if actually wanted to push it any further. I went through my first big agonising Quit and decided to fold the project in March. I remember thinking, ‘I am working two part time jobs I don’t like in order to work on my own project — it HAS to be one I want to do!’ I have not regretted it.

Meanwhile in November I bought 30 ukuleles and I got my first booking for Power of Uke! That year was spent building up a website, trialing workshops and taking part in the 3 month Hatch Accelerator.

Yes, there were four projects on the go at early stage that year — but it was the scattergun approach!

Lived in: Kennington

Life-changing book: Essentialism

Best moment(s): Our first magical Creative Retreat

Hardest moment: Deciding to quit Pasaporte Cultural


Another powerful year.

In September I went to the Happy Start Up Summer Camp and had a life-changing conversation about my relationship with money. I sought out a money coach and started a big journey of unravelling unhelpful beliefs. ‘No-one really knows their relationship with money until they’re self-employed,’ my coach said.

Creative Retreats and Rye Laughs were still going strong, and bringing in money now. Power of Uke got it’s first big corporate gig, making it the first project to reach Level 4.

We started running Creative Sundays, as a gateway to our Retreats, which were gorgeous meet ups on Sundays with coffee, writing, sketching and connecting.

I regularly found myself as the Playlist Queen at parties and got asked to DJ at various friends’ weddings. We had consultations for the music, organised silent discos and I had the time of my life!

Around April time I stopped drinking for a month, Marie Kondo’d my room and realised that it was time to leave my Assessment Centre job, and London for a bit… and move back with my parents in Devon. I was absolutely exhausted and needed to recalibrate and catch up with all that had happened.

Lived in: Kennington

Number of Weddings: 7

Bridesmaid: 3 times


Life-changing books: Marie Kondo, The Art of Asking (Amanda Palmer)

Best moment: Realising that I could move to Devon!

Hardest moment: Break up with Joey, and difficulties running Creative Retreats


Another incredible year full of expansion and new ventures…

I spent the Autumn living in Devon, which gave me some much needed space, rest and reset. For the first time in my life I didn’t have every evening booked up with social engagements, and I LOVED it.

It did so much for my professional confidence to call Power of Uke my main source of income (even though it wasn’t much) and AirBnB approached me to be one of their pilot ‘experiences’, running ukulele walking tours.

I had time to be creative: I took DJ lessons, attended movement meditation in Exeter, and held the space with the music for the final dance of the year.

Back in London in the spring I lived like a tourist, moving house every couple of months and exploring different areas of the city. I organised a massive ukulele jam for Pancake day for about 40 people in our Canalside flat!

While in Devon I had let go of Creative Retreats and almost immediately made space for a new project — a new accelerator for Female Founders, which I designed and facilitated with my previous mentor from Hatch — Helen. It was all around well-being and building a business around the life you wanted to create. I brought in friends to speak, run workshops and coach — it was a really special experience.

I attended a Practical Philosophy course and began to familiarise myself with the moon.

Rye Laughs was given the opportunity to run a week-long takeover, and I was in my element co-ordinating workshops, performers and DJs for our mini festival.

I took 5 weeks off in the summer to walk the Camino del Norte and even led a Spanish themed Project Awesome workout before I went!

One of the reasons this year was so good is I started working with my super coach Emily Johnsson, who worked with me to reframe the belief that it was selfish to enjoy my life, play and feel in flow. There was a lot of resistance.

Lived in: Devon, Dalston, Haggerston, Bermondsey

Travelled to: Camino del Norte

Significant mentor: Emily Johnsson

Big books: Insanely Gifted, Moonology

Best moment: A day when I taught a money workshop in the morning on the Female Founders Accelerator, then performed and hosted the Clowning Night of the Rye Laughs takeover in the evening, followed by my mates DJing the bar and partying hard. Proper flow day.

Hardest moment: Days on the camino when I needed to rest and was EXHAUSTED.


Back from the structure of the Camino, I really struggled.

Work was dwindling and I felt really low in myself. I reluctantly took on supply teaching again, and it broke my heart.

The Female Founders Cohort 2 were challenging and I was experiencing a values clash with the organisation.

Two things temporarily brought my buzz back that Autumn:

  • Being accepted to deliver a TEDx at my old uni around the topic of Quitting.
  • Doing the Showstoppers musical improv course

The process of writing the TEDx was a huge learning curve. I loved walking in Highgate Woods to carve out my talk, but once it was written, I struggled with the 3 months of ‘practising’ and ‘perfecting.’ Everyone I shared it with had an opinion, and I lost myself a little.

I also ended up in hospital with extreme stomach pains, although nothing was ever medically wrong. The doctor asked me if there was anything that could be causing stress, and I realised the irony that I was writing a TEDx about listening to your body. ‘Sometimes we teach what we most need to learn,’ the GP said.

Those winter months were hard financially and emotionally— I wasn’t sure where my money would come from and I no longer had a regular income. Then it snowed, all my work got cancelled and I got flu. I remember one day just crying myself to sleep as I was so fed up of it all.

I was also living in a house share that didn’t work for me, although it taught me a hell of a lot about honest conversations and asking for what you need.

Somewhere in the middle of this, I created the Quitting Quadrant. People talk about downloads, and this was the experience I had: I opened my notebook and a model to help people with quitting poured onto the page. I stayed up all night writing, re-wording. I was so excited!

And then I started looking for somewhere else to live and finally found my House of Dreams, living with Iona, and I’m still there now :) I can’t tell you how healing it was to live in a place with people who totally accepted me, who loved that I did moon ceremonies, who joined me in the musical sing-a-longs… ahhh it was total liberation.

My coach Emily said to me, ‘Sarah, if you can write a TEDx and create the QQ from that basement, just think what you can create now you’re in a place you’re happy in!’

In the summer things started to look up:

  • Power of Uke went from non-existent to landing a huge contract with PwC — another thing that boosted my confidence and really took my business to the next level.
  • I recorded a comedy video about GDPR and it went viral! 100,000 views across Facebook and YouTube — I even got booked to perform it at a summer party :)
  • I got into a musical improv group called Acaprov — and found myself in total flow state freestyling raps and making up songs with other musical enthusiasts!
  • I also applied for a full time job at Monzo bank, got an interview, shared all the stuff that I was up to, realised my life was quite cool, and was secretly relieved when I didn’t get the job!

Lived in: Haggerston, Archway, Crofton Park

Travelled to: Vienna (for 5 year party of Teach for Austria), Camino (this time with Kate and Jo)

Supported by: Emily Johnsson, Penny (my mentor for the TEDx), Alex Mecklenburg

Big Books: Rising Strong, You’re a Badass at Making Money, Loving What Is, Playing Big.

Best moment: Sending out my survey for the Quitting project and being inundated with beautiful responses.

Hardest moment: Challenges with flat and not having anywhere to live.


This year Power of Uke really grew — I was working regularly with PwC and building up my confidence, making regular sales from my taster breakfasts and finally feeling like I had something of value to offer!

I put on an Assessment Centre to find my new team members and had 20 applicants. I chose four amazing ‘FaSILLYtators’.

My QQ evolved — I ran an online pilot in the new year for 25 people, coaching them through different activities and usage of the QQ. I was also invited to present the QQ at Google in London and Zurich, and at a start-up conference in Italy.

The moon circles really moved up a notch — we started to regularly hold them at our house, and on friends’ boats. And in a post-festival slump I created Sarah Moany, a nonchalant Aussie spiritual ‘healer’ who records moon videos for our moon group every month. She gives me a lot of energy!

Our house regularly hosts events, including ‘Day of Musical Joy’, a full day of singing with friends creating a concert from scratch.

I took a punt and booked some holidays (Colombia and California), then had to do some supply teaching to fund it. I had a dreamy set up teaching only THREE year 11 pupils Spanish GCSE, and starting school at 1pm each day. Total change from Teach First days.

I ran my first half marathon, did a coaching course and started taking on paid coaching clients, all from referral.

I started working with my own coach, the magical Kate Taylor, and after our first session I found out I was compering and DJing at Glastonbury for Greenpeace (a big bucket list item for me!)

Having a house I felt happy in was my rock this year.

Lived in: Crofton Park

Travelled to: Colombia, Portugal (Silent Retreat), San Fran, Yosemite and L.A

Key mentors: Kate Taylor, Jody Shield

Big Books: The Surrender Experiment, The Prosperous Coach

Best moment: Being on stage at the silent disco playing Defying Gravity to a room full of ravers at 3am and seeing everyone go wild!

Hardest moment: When a huge piece of work got cancelled after Glastonbury and I was left with no money.


The final few months…

I got a huge contract with Google to regularly facilitate on their Exec Labs and battled with big imposter syndrome.

I’m regularly running Power of Uke for Google Sprint Labs and have made some good friends in the team.

I trained up 4 new ‘Fasillytators’ to run my uke workshops and they’ve been fab! Power of Uke now has a ‘methodology’.

Rye Laughs celebrated its 5th Birthday. We’re on our 4th venue now and have a solid regular crowd.

The ‘Carousel’ concept came to me in another download — a model for people who prefer variety over one focus. I’ve created a newsletter and spoken on podcasts all within a few months. It feels like it’s evolving into something bigger.

Our house has continued to host with regular moon circles, and two more Days of Musical Joy. My housemate Iona and I also put on a Christmas Singles dating night. There is a lot of creativity and fun around.

I stopped drinking for 90 days, which cleared up a lot of mental clutter and started working with a personal trainer.

Lived in: Crofton Park

Big Books: Do Less, Sober Curious, The Big Leap

Key mentors: Kate Taylor

Best moment: Christmas Day of Musical Joy — singing 2 Become 1 at the top of Blythe Hill fields

Hardest moment: Running the singles night! Brought up a lot for me — but I’m glad I did it…

I’m ending the decade feeling really proud of all that has shifted, noticing that most of the things in my life are things that bring me joy and that I would choose to do, whether I was being paid or not. Looking ahead at 2020 there is a lot of space, and part of me feels anxious to fill it, but I also am really excited to see what drawings appear over the next few years, as long as I keep following the joy…

Thanks for reading :)



Sarah Weiler

I’m a multi-passionate TEDx speaker, writer, coach, framework-fanatic, quitting researcher & ukulelista/composer. //