Escaping the 9 to 5 with Dave Ursillo

This month’s interview is with Dave Ursillo, and I can’t really fathom why I didn’t ask him sooner. Dave and I met at the Alive in Berlin conference last May 2015, where he spoke briefly about his career transition as well as taking us through a ‘7-Step Chakra Guide to Being Alive’. We’ve stayed in touch since and I was glad to have the opportunity now to hear more about his experience of leaving politics behind for something a little different…

Dave’s story is another one where his personal values played a crucial part in his decisions (see also Ryley’s interview from earlier this year). I love his journey of finding a way to stay true to who he is while making it work from a financial and commercial perspective. He also shares some fantastic insights about how to create a balance between freedom and structure in your daily life – something I’ve struggled with myself – as well as how to tell your story in a succinct way (well, he is a storyteller, after all). Watch the full video of the interview to get all of Dave’s fantastic advice!

Coach for creative people

Dave Ursillo is a writer, business storyteller and yoga teacher, having come from a background of politics and public service. In 2009, he left his job working for a politician at the state level. He had gone into this career hoping to use his skills and passions as a writer to be a part of positive change in the world but he found that politics was not the right avenue for him do this. Today he teaches what he loves – writing, creativity, yoga, artistry, personal development and all things self-expression – via workshops, his online writers’ group, and one-on-one sessions with clients.

1) At what moment did you decide it was time for a change?

There were a handful of moments.

It was weird for me because I was working with people who were really good, and who I really enjoyed. But when you’re in the game of politics, when it becomes something of a power grab and the egos get involved, then you see people’s worst natures coming out, and I remember seeing that and feeling it. I knew that there would be a lot of situations, from basic conversations to actual events, that would prompt me to have to choose my true nature – as a guy who wants to do good in the world – or cut corners and make excuses, making exceptions to get ahead. That was something I never wanted to put myself through, because I knew it would tear me apart. I was already dealing with depression at 23, without having gone through all these difficult decisions to compromise on my moral integrity.

So it was an accumulation of a lot of moments and noticing, observing, and listening, to a lot of different people and places. Once I got that sense of what the culture is of a business like politics, I made the decision early on that I wouldn’t be able to compromise and live with myself. I knew that working for myself, and starting a blog, and trying to freelance and do things to make money would provide enough social validation, or an excuse, to do what I ultimately really wanted to do, which was write books and be poetic and live a healthful and fulfilling life. I didn’t really know what shape that would take – and I still don’t know which shape it’s going to take in the future – but I had the freedom of not knowing. The uncertainty is so crippling; every day I deal with that same feeling: what am I doing? But that’s just the flip side of freedom: not knowing, and not being shackled to predictability or expectations or assumptions.

2) What was the biggest challenge you faced in making the change?

There were so many unknowns. I was really making it hard on myself to figure everything out on my own. I was leaving a job, leaving a career; I was trying to start a blog, a platform, something new for myself; and at the same time I was also trying to rationalise and heal different wounds that I was carrying, with depression – mental, emotional health. So I was really trying to do a hell of a lot! Some advice that I give to people if they’re starting out or if they’re in this transition is: don’t go it alone. The transition was difficult for me early on because I wasn’t breaking out of my shell, or reaching out, putting myself out there, and risking to be told “no” or risking failure.

I’m very hard headed, I’m very stubborn and independent minded, and hands-on experience is the only way I ever retain knowledge. So in a sense I needed to figure it out on my own; but I wish I had reached out more to people early on. It wasn’t until maybe after at least around a year, a year and a half, when I started to break out of my shell, even though I was writing and blogging, it really took me a long time to start to make connections with people. At the time, it was Twitter and blog comments and things like that, which helped me start to knit a little web of people, connections, who were doing something similar to me. That was enough to start to get these doors opening: friendships, even long-distance digital friendships, that were supportive and nurturing.

There was also the quiet shame of: “I have no idea what I’m doing.” And I didn’t want people to know that I didn’t know what I was doing! It took a lot of build up to break through that and realise, that I have to do something, in order to be of service to people.

3) Where did you get the support you needed to make it happen?

I had great support from my family. At the time, I was 23, I had no debt, I was living at home; so I also had the financial stability and lack of commitments to be able to quit. I thank my parents for that, for giving me the space to try something really new and different, that they had no idea how to understand.

When I was about to quit my job, I knew I needed to sit my parents down and explain the vision that I was having for what could be, and I put together a PowerPoint presentation! I enunciated what I was going to do and how it could make me money and how it would be valuable to other people. I had different projects in mind, and I was basically explaining a marketing funnel – but I wasn’t using those terms or making it about the money, I was saying: this is how I can create something from nothing using the internet. I needed them to understand enough about what I care about, without knowing exactly how it was going to turn out. It was a very foreign idea so my parents were very supportive in giving me the leeway to figure it out for a year or so as I continued to live at home.

4) What’s the best part of your lifestyle today?

It’s the openness, the freedom. I love not having a predictable day, and I am very averse to scheduling. I do schedule plenty, I have deadlines for myself on my phone, I use an app like Asana for to-do lists, I use the Calendar app to keep things organised and keep my mind in order… but it’s the openness of a day, where I can wake up and I know I have things that I have to do, some obligations, some expectations, meetings, phone calls – but ultimately it’s the undertone of the ability for me to cater my day, my experience, my journey in a way that honours me fully; and honours the people around me. It’s a very yoga-like perspective for me.

I don’t get a lot of value from just executing things on a to-do list but being very responsive to what I’m feeling, what I’m experiencing mentally, emotionally and spiritually. For example, being able to carve time out this morning for writing and coffee on the balcony here, and stumbling upon a poem, or a book idea, or something like that – this is just as valuable to me as executing a blog post or something like that. The openness and the space can be very daunting, very overwhelming – again, the uncertainty is the flip side of freedom – but I’ve come into a healthy relationship to those things because I realise at the end of the day how much I value having the space to be responsive and creative and to go with the flow.

I also cater my schedule to the time of year. When I know the next day is going to be beautiful and I want to be outside as much as I can, I might work a little bit more the day before. If it’s a rainy day – and here in New England we have some really rough winters – I try to hustle and burn through a lot of work just to keep my mind occupied and moving. Then I can reserve my summer for doing less!

There’s also your own psychology: one of the metrics that I use to assess how my workload is doing is whether or not I’m avoiding certain aspects of work. I’m avoiding things like working on my next book; digging into that client work that I’m afraid deep down that I will somehow not be able to accomplish. The things that I’m avoiding reveal caring, and the stakes being higher. When the avoidance is there, I know I need to lean in and burn through it.

5) What one piece of advice would you give to someone who is considering making a big career or lifestyle change?

If you’re thinking about quitting your job, I would encourage you to fully give yourself to the idea; if you want to work for yourself, if you know deep down that you have to leave your job for some other reason. Start to try to get paid for things ‘too soon’, before you think that you’ve deserved a dollar value for your services. Start to ascribe more value onto yourself before it’s too late. Know that your worth in service to people is such that people will be willing to give your their money in return for your time, your efforts, your services. When you’re working for yourself and you’re creative, it necessarily becomes a very personal and soulful experience: you can’t be cold and detached about assigning dollar values to the work that you do.

If I had a lot of financial obligations and expectations, I would probably need to know how to make money sooner but I had the privilege, the opportunity, the luck, to not have to provide so much for myself so early – so it’s a matter of your circumstance and your situation. It’s also who you are as a person: some people work really well under deadlines and pressure to perform. I’m an ‘all-in’ type of person, I can’t half do anything, I need to be all-in: emotionally invested, mentally invested, totally into it; so I knew that if I was toying with the idea to write an ebook to make a few dollars per sale on my blog while I was working, that ebook would probably never get done. So consider the circumstances, the practicalities that you need to satiate, and also what’s your nature.

You can find Dave at daveursillo.com or request an invite to his Literati Writers Group on the site, or email him at hello@daveursillo.com.

Have you made big changes in your life and want to inspire others to do the same? Or maybe you’re 100% happy staying put where you are and want to make a case for being satisfied with what you have? Get in touch to share your story!