List 4: 30 Risks I Took & What I Learnt

30 Lists of 30 to Celebrate my 30th Birthday

21 min readAug 4, 2021

The What & Why Behind This Project:

This year I turn 30. And my gosh, I have been thinking about it a lot. I don’t know if it’s the pandemic, or the fact that this milestone is loaded with many societal expectations, but my mind has inundated me with reflections and memories from the past, with questions arising about my life choices and lesson learnt, about my expectations of being a human and about my desires for the future. And this combined with pandemic reflections has meant there has been a lot on my mind….🤔

I started writing a series of questions and lists of all the elements I wanted to capture and articulate. There were a lot, unsurprisingly; 30 years is a long time really! So I gave up on the 1 list idea that I normally write (30 reflections/lessons turning 30) and decided to write 30 lists.

30 Lists of 30, for my 30th Birthday.

Who are these lists for, you might wonder? I started writing reflections many years ago to get to know myself better. And when I shared these raw and real accounts with friends I discovered that what I wrote about my individual journey, touched upon something universally human. Beyond the masks and labels we wear is a messy, beautifully complex life, with highs and lows. And more similar to others than we might think.

So I share them in the hope that you too might feel something — intrigue, joy, resonance or maybe even difference — as you reflect on what it means to be a human. I recognise that my experiences are my own, that some come from a place of privilege and that they may not all be relatable or interesting to you. I know I can’t please everyone, so take what you can…(and let me know what lands!).

So, Back to Lists…

The Why Behind List #4:

Our lives are made of thousands of decisions, and every decision involves some nature of risk because it’s impossible to know exactly what will happen. And unlike the good stuff in life, it is often the mistakes/the challenges/ perceived failures or out of comfort zone decisions that create the deepest learnings that then stay with and direct us for the rest of our lives. I’ve come to realise that I’m a medium-high risk-taker — I take bold-ish moves although they feel calculated as I spend a great deal of time deliberating and mitigating risk. One thing I am learning about taking risks is to reap the benefits of taking risks also means accepting that sometimes the decision was not the best one or that there will be negative outcomes occurring you could not have conceived of. The unknown unknowns. It’s fun to look back and explore what I could have known or not, what motivated certain risks and what I did learn from each one.

List #4– 30 Risks I Took & What I Learnt

Moving back home with my family during the pandemic. After around a decade of spending no more than a few days altogether in the same house, I was a little worried that we might all kill each other. Especially since we couldn’t leave the house much. The result was quite the opposite — we got to know the more adult day-to-day working versions of each other, share (and co-create) the small mundane moments of everyday experience that actually a relationship, create new rituals together (e.g. every evening someone would cook a new cuisine and serve it at 7.30pm complete with candles and music that connects to the cuisine), laugh at each other’s everyday routines/ habits (e.g. daily naps, speaking really loudly on calls, playing the same songs on repeat, way too much coffee), go on walks and bike rides together and have a surprisingly low number of real arguments. Of course I missed my own space and London life, there wasn’t much ‘life’ I was missing due to the lockdowns. Although I wouldn’t choose to live with my family forever, it made me appreciate both collective living and the chance to truly reconnect with my family. There are always silver linings to the Pandemic.
Choosing to have surgery on my foot (tarsal coalition resection) that then led to two more (unplanned) surgeries when I lost feeling in my foot (tarsal tunnel nerve damage), and then experienced substantial pain in the other side of my foot (bone spur). This was one of those decisions that with the ability of hindsight I can say was not the best decision, but that I made the best choice with the knowledge I had at the time. After a lot of running injuries in the run up and during my marathon and ultra marathons in 2012, I sought consultants advice on the true cause of the problems. The scans indicated that my tarsal bones were coalitioned from birth, which was restricting the movement in my foot when I ran, and I was assured by two separate consultants that surgery to break the bones apart was possible and could have a high positive impact. What I didn’t understand at the time was the possible damage that could occur when you do surgery — like nerve damage, scar tissue and a substantial rehab programme or physiotherapy that requires a rewiring of how I move and that might not work well. I’m grateful that my nerves were only compressed and not broken so most feeling has returned, and that I’m able to run still (only a little right now but I’m building up slowly). But I could never has imagined or desired a world where I daily running wasn’t a part of my life, where I would spend my 20s searching for and exploring a plethora of podiatrists, physios, sports massage therapists, consultants etc. as a part of my everyday life. What was the learning? Don’t trust or at least be highly cautious of authority and their truths, which are always biased or incomplete,and recognise and understand deeply the negative impact of risks (even if the chances are low). Having a fully functioning body is a gift. Treasure it, look after it, empathise with those who don’t have it.
Choosing to staying at university despite being physically and mentally unwell. In my first year of university I was depressed, unhappy (with my course and my friendship circle) and suffering from bouts of severe fatigue that made me sleep for 10–15 hours a day, and no doctor really understood what was wrong with me. It was quite possibly the worst year of my life (ironically, the year before was one of the best) and most days I felt myself fall further and deeper into an abyss. And despite kind support from my Mum who suggested I restart elsewhere, I realised that new contexts or solutions aren’t always the answer — they have their own new problems. My problems wouldn’t disappear overnight. Sometimes staying where you are and recognising your own ability to positively influence multiple aspects of your life, and that this takes time, is in the long-run a more effective strategy.
Dropping one of my degree subjects (it was a joint honours course). Despite loving Theology at school I did not vibe with the subject or the way it was explored on my undergraduate course. A large part of me wanted to just suck it up and hope it would get better as I was getting pretty good grades but I realised that the resistant part of me that didn’t like it wasn’t going away and that I might as well do the degree that I enjoyed and made me feel energised, even if my grades were affected. Philosophy assessments were hardcore so the risk I took was a dip in my grades but I realised that if you really connect with what you’re working on you’re more likely to put in the time and effort to deliver high quality. This was a good lesson in following the things that bring you curiosity and joy.
Calling my organisation ‘Trigger Conversations’ — Trigger being a negative world for some of the world. I received this feedback early on but decided to go ahead regardless because I liked the name, and then experienced some challenges with global audiences later on in Trigger’s journey. I’m still undecided what the risk of keeping the name is and whether to rebrand because there is now a lot of publicity out there under the name. I guess the learning here is to think more long-term about projects, but also to recognise that most things can be changed too.
Unintentionally annoying a supervisor and not getting promoted when everyone else did. Whilst at university I was part of the University Officer Training Corps (OTC), a part of the Army Reserves. It turns out that my slightly direct, sometimes cheeky and challenging (of decisions and ways of doing things) approach didn’t align with the strict Regimental Sergeant Major (RSM) and when it came to the end of the summer camp where they promoted my cohort to Junior Under Officers (JUO), they decided not to give me the position. Naturally, I was disappointed and frustrated as I was singled out and it had never happened before. Instead they offered me a different and new role — Adventurous Training (AT) and Sports Coordinator — which ended up being an absolute dream as I had full freedom and reign over the unit’s AT curriculum and worked to my strengths designing and delivering a range of experiences for everyone. Even better too, 2 months later one of the new Training Officers got to know me and wanted me to lead a section of cadets, so convinced the Unit’s Commanding Officer to promote me to JUO whilst the RSM was away. I ended up keeping both roles, was promoted again a year later, and received three awards in my four years’ serving there. I learnt that I won’t always be chosen and that being totally yourself means that you won’t always rub people up the right way. But that there will be people who do like me and will fight for me. I also need to trust that sometimes you have to take one step back (or it seems like that) to take three steps forward.
Applying for deferred entry to university and highly limiting my university options. I discovered only after applying and getting turned down by many universities, that most don’t like offering deferred entry spaces on a joint honours degree to students (because they are so limited). As an ‘A’ students with a host of extracurriculars and some nice references, both my tutor/teachers and I were surprised, but by then there wasn’t much I could do except reapply or accept the limited choices I was offered. In the end, after some panic about not getting into the place I wanted to go to, I picked one of the two universities that did accept me and went off and had the GAP year I had wanted without having to deal with reapplying. That GAP year — a mix of working, learning and travelling — turned out to be one of the best years of my life, and the university I went to I did enjoy in the end. Not knowing about the nuances of the application process for deferred entry was an unknown unknown and sometimes we get the options we don’t on the face of it want, but can actually be pretty happy with!
Quitting my consulting-esque job 3 months in without another one to go to. I was on a sort-of-graduate programme that had been sold to me as fast paced, full of learning and responsibility but I found myself stuck taking minutes, booking meetings and getting heavy pushback when I tried to take on more. I was miserable at work, clock-watching for the first time in my life and most people told me that that was the nature of work and that I should stay for at least 2 years as it would look bad on my CV. I deliberated and eventually, after a week’s holiday where I re-fell in love with life, I realised doing meaningless work was really affecting me and a waste of my time, so I handed in my notice on the first day back. I didn’t have a job to go to but got in touch with colleagues from my previous role who suggested a role at a partner institution that was way above my current pay grade and level of responsibility. I almost didn’t apply because of that, but with their support and good words, I applied and was offered the position to start immediately. Sometimes removing something from your life creates the space for something new to appear. I also learnt about the power of building great relationships and not being afraid to draw on them in times of need.
Taking on 2 degrees and a couple of jobs at once. Whilst doing my undergraduate degree and working at the University Officer Training Corps part-time (doing two-three roles), I decided to treat myself like I was invincible and take on a part-time Masters at another university. Why? Curiosity mostly. It was a pilot programme in Emotions, Credibility and Deception, from an applied psychology and linguistics angle and, having followed a related organisation for a long time, it fascinated me. I didn’t want to wait a year or more as I feared it might not run again, and I found a way to make the dates work for both universities so I didn’t miss any live sessions. What I didn’t think through was the added stress of having double the amount of assessments, often due at the same time, and how my part-time Reservist work might also increase in intensity during certain parts of the year. The result of this was illness over a 2+ week period and the need to get extensions for most of my assessments. My flatmates thought I was bonkers, and a bit naive. I think I was overly optimistic about my invincibility. I managed it in the end, getting a distinction for my Masters, but there were tradeoffs with my undergraduate 2:1 being a little too close for my liking. However, I learnt a lot about how to manage multiple projects at one go, that can actually engage different parts of the brain (and enjoy doing so), cross-pollinating my ideas (I used my Army Reserves work for my MSc thesis) and keeping me feeling fresh! To this date, I’ve never had just one project and the idea of commiting to one thing doesn’t feel me with joy.
Not having a post graduation plan. Whilst many friends spent months applying for large corporate graduate schemes, I decided not to. I didn’t know exactly what I wanted to do, and I didn’t want to commit to something full time immediately either as I had a part-time Masters to finish. However, in the days around my graduation I did get the classic panic and anxiety of not having a plan (I had applied for a summer internship at Cancer Research UK which I hadn’t got), and comparing myself to many of my peers who had at least something. Soon after that anxiety I was propelled into action and discovered an internship at a startup that resonated strongly with my values and skills and I applied, and was lucky enough to get it. The rest of that year I allowed myself to run a series of experiments — taking internships and jobs that were short term, allowing myself to discover if I liked the work or not (and what elements) and to allow opportunities to emerge from these short term commitments. Both internships turned into part-time roles. In reflection, allowing myself to take the risk of not having a full-time role gave me permission not try on many hats and to get stuck in a role that I didn’t like.
Long distance relationship. It definitely wasn’t the plan to date someone at the other end of the country, especially someone who had just left the city I was living in at university, but then life doesn’t always happen the way we want it to! Having a long distance relationship for over a year taught me a lot about intentionally using the time you have together well, recognising and valuing the decision to make a greater effort to be connected and finding joy in the micro-moments, on the phone for instance.
Giving myself a few weeks to write my whole MSc dissertation — which then didn’t happen because my life then fell apart because of a relationship breakup and then surgery on my foot (#3). Reflecting back on this tight timeline, I recognise that I didn’t allow space for life to happen which its peaks and troughs, and I forced way too much pressure on myself to perform.
Commiting to a stranger at a festival that I would create and launch an events around meaningful conversation in a few weeks. This was how Trigger Conversations began and it was one of the best risks I have taken because it forced me to create something real in the world. I’ve learnt that social accountability is a really good driver for me to get stuff out there (like this 30 Lists project!).
Starting a business with little start-up experience. It was at once both wonderfully optimistic and also naive when I jumped into entrepreneurship. There is so much you don’t know and need to learn, and a part of me wonders why I didn’t spend more time working for others in a startup to learn what works, and get paid for it! And yet, when the passion for an idea is there and there is a desire to keep learning, well… perhaps that is enough? Reflecting back, maybe more experience working inside organisations would have benefitted me, but I also acknowledge that if I had done this then I might not have experienced the same accelerated rate and breadth of learning when you are thrown into a very deep pond.
Not applying for a normal job in 2017 and using my savings to launch my company Trigger Conversations. I remember telling my family and friends I wasn’t going to look for a job after my fixed term contract ended, and instead would see if I could make Trigger a thing, a business that would support me…. they thought I was brave (and somewhat naive!). Now I understand why! But I felt I needed to completely step away from something full time to give me the cognitive and emotional space to explore my identity and see what would emerge when I stepped into a new environment of possibility. As expected, I burnt through my savings — that was a good lesson to learn — but I also made money from day 1 of my business, running it extremely lean from the beginning. Looking back, having a back-up part-time job (and one that couldn’t become full time, even if I wanted it) would have been beneficial by reducing the stress involved when running out of money.
Posting about my conversations idea on a Facebook group and talking to people about it at events. This might not sound like much of a risk but at the time I felt like an incredible imposter — who am I to share my idea? What happens if no one likes it? There were a few who confused by the concept but most weren’t and many were delighted and curious and wanted to find out more when I launched. The practice of talking to 5 people at an event was instrumental on the ‘making journey’ — it gave me the feedback I needed to hone my pitch, understand the problem deeply and the inspiration to get out there and make it a thing!
Contacting Henry at Escape the City about partnering with them for a Trigger event in 2017. I was a very new startup idea and they were a fairly well established organisation with a large following — I remember thinking that they wouldn’t be interested in me and other imposter syndrome-esque thoughts. It’s a good thing I asked anyway as that one event led me to meeting a large number of (now) good friends and business collaborations.
Offering a (new) friend to do my marketing for Trigger. This was one of the biggest risks I took for Trigger, as it committed me to paying someone else every month, and therefore to making sure we were in profit. There were months where we struggled, but having the support of someone else on the team to bring me up when I was down, to brainstorm new ideas, and to take ownership over one of my less favourite parts of business — marketing — was a savour. Being a solo founder is hard and I don’t know where the business would be today if she hadn’t joined me.
Scouring the internet for conversation-esque courses and showing up to a Your Charisma Coach bootcamp. In some ways there was little risk here, as I simply followed curiosity and showed up but maybe the risk was in trusting that something useful might come from this investment. Those few days led to some breakthroughs in me understanding what beliefs were holding me back (in life), brought me a mentor, a friend and a business partner and then led to me becoming a trainer for another organisation, which gave me the confidence to run my own a few months later.
Doing my TEDx. Not a huge risk, except that standing on a stage and delivering a 13 minute speech I have learnt verbatim to 150+ people is actually a little terrifying. I remember shaking delivering it (not noticeable on the video!) and being so focused on staying relaxed so I didn’t forget the next line. I guess the risk of public speaking generally is that it feel like there is a lot to lose reputationally if you forget your lines or don’t deliver something well. I’m noticing nowadays how okay I am with public speaking which suggests that continually putting myself through public speaking experiences has paid off! The best way to get better is just to do…
Saying yes to corporate work I’d never done before and then figuring it out after. Since engaging in entrepreneurial freelancer work, I have discovered this is incredibly normal, even though it can feel really hard to commit to doing something for money that you have never done before and don’t always know how you’ll do it. I’ve realised since that as long as your confidence is founded (you’ve done something in the same field or related), you’ve got a growth mindset and a good network to draw on for resources or collaborative partners, these are usually the best opportunities to take because you’re always stretching yourself.
Going on (facilitated) plant medicine retreats to heal my trauma and deepen my relationship to myself and reality. I deliberated on this for years, reading up a lot on the possible negative outcomes and talking to others about their experiences. At the time this felt like the biggest risk I had ever taken as I grew up very anti-drug of any sort with an extreme set of anxieties about what might happen. I do think it is extremely important to be highly cautious and careful (especially with the space, setting and substance), but I also recognise that what is shared in the media or common opinion may not be nuanced or based on the latest research. I’m glad I took this risk as what I did gain was one of the most healing, fascinating, loving, nourishing and deeply connecting to earth and reality experiences I have ever had.
Asking a guy who ignored by messages, on a date, via voicenote. The backstory is that we had already met and were friends on Facebook but hadn’t spoken in years. I knew our values and interests overlapped and I was curious if there would be a connection — romantic or even just friendly. I had created a story in my head that he wasn’t interested because he hadn’t replied to my messages on a dating app, but I also knew that it was possible that he was a crappy replier and that the only way to find out was asking. Often we don’t complete the feedback loop because we don’t take a risk and find out what could have happened, and instead just stick to our (untested) hypothesis. What happened? I know you’re curious… I got a voice note back within 24 hours saying yes, let’s meet!! Due to COVID it took up 6 months to meet in person. But it happened. The risk was worth it. And even if he had said no, or not replied, I was proud of myself for having the confidence to go first and share my desires and it encouraged me to do it again.
Severely reducing my business offerings dramatically to save my health in 2019 and trusting that the universe would bring me work gigs (inbound, rather than outbound). At the time I was so fearful of doing less as I felt it would highly impact my brand, and also influence my income to live, but I also didn’t feel like I had much of an option because I was unwell and deeply needed rest. I was lucky/ had built enough of a name for myself and the business that I had enough incoming requests for work that saw me through many months of living, whilst also giving me the time to work on my health. “Leap and the net will appear” shares Julia Cameron in The Artist’s Way — sometimes you don’t know how things will work out but they do.
Giving friends, family and collaborators feedback when something isn’t working. These days I take this risk pretty often if I notice it is impacting our relationship. Sometimes this goes incredibly well, sometimes ‘medium’ and sometimes they feel attacked and upset because I didn’t set the context well enough upfront (especially when feedback conversations are rare for them). I’m still glad I continue to take these risks because the only way to get better is through practice.
Choosing to not apply for a human engagement and performance role at Deepmind, Google (a super-forward thinking organisation that could be open doors and create a good income) in 2021. I haven’t applied for a job for years but chatting to the recruiting partner, it seemed that the role was a good fit and I did feel excited about it. A few friends told me I should seriously consider the role, delay starting my PhD and that I would regret not going for it. But delaying the PhD is not something that I want to do right now.
Writing (and publishing) these lists. When I told friends about this project the classic response was ‘how many items is that.. 900?!…Georgie, that is a lot!’. And they were right — I have certainly felt stretched getting some of these lists over the line on time. The other element of risk here is the personal nature of what I am publishing. I have definitely felt the vulnerability hangover getting words onto the page, even before they were shared with anyone. I guess there is a fear that they will be read out of context, misunderstood and this might lead to judgement and or less opportunities. I accept this might or even will happen, due to the imperfect nature of communication, and sometimes we just have to live with that.
Speaking to strangers all the time. Some of the reason I started these social freedom exercises was to work on my own anxiety around approaching new people, and I remember feeling almost sick before I did it. Sometimes people would reject me but rarely — this mostly taught me that I had created stories and assumptions in my head that weren't true!
Investing in my own education. I have spent a lot of time, energy and funds working on myself, in the hope that I will be helping future Georgie achieve her goals to deliver impact. Although resource heavy, I think that this is one of the best risks I could have taken — because I feel so much more agency and confidence to do the things I want to do in life.
Putting my ideas and perspectives into the world, and trying to live according to those ideas and principles. Believing in your own crazy ideas and sharing them with the world can make you look silly or wrong. It has taken me years to get comfortable doing this but I am grateful to myself for allowing myself to share an idea that not everyone understands or to get it wrong in public.

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Want To Read More Lists?

I’m publishing one list every day in August (and will add the hyperlinks below).

Want To Read More Lists?

I’m publishing one list every day in August (and will add the hyperlinks below).

Follow me on Medium to read them.

Still Curious?!

💬 Watch my TEDx talk: Talking to Strangers: Having a Meaningful Conversation

📖 Read about some of my work recently published in Entrepreneur.com How to Become a Master at Talking to Strangers

✍️ Stay connected through Conversations With Georgie: The Home of My Thoughts as a Life-Long Learner. Curious. Deep. Exploratory. Real and Raw.

📧 Contact Me: Georgie@Triggerconversations.co.uk

List 4: 30 Risks I Took & What I Learnt

30 Lists of 30 to Celebrate my 30th Birthday

The What & Why Behind This Project:

So, Back to Lists…

List #4– 30 Risks I Took & What I Learnt

Written by Georgie Nightingall