List #23: 30 Lessons from 5+ Years of Entrepreneurship and Creating

30 Lists of 30 to Celebrate my 30th Birthday

11 min readAug 24, 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 #23: 30 Lessons from 5+ Years of Entrepreneurship and Creating

When I started my business ‘Trigger Conversations’ in 2016 I was a beautiful mix of driven, optimistic, naive. All the qualities needed to found myself, and stray on tracks that are my their nature risky, stressful but profoundly rewarding. These last 6 years have been rich in experience, heavy in learning and at points, incredibly stressful. You have to go through it to really understand but for those who also want to leap into the world of entrepreneurship or creating, there are certainly elements one can learn from others ahead of time.

List #23: 30 Lessons from 5+ Years of Entrepreneurship and Creating

Discomfort is mostly just a sign of unfamiliarity, and unfamiliarity is the gateway to growth. Lean in 95% of the time.
You will burn through money faster than you expect to (for living or the business). Have savings backed up — and more than you think you need- otherwise the stress of the runway will make it really hard to focus on building. For me when the bank balance is low I revert to a scarcity mindset which affects all elements of my life, and affects my ability to sell and make money.
Who you spend your time with will define your mindset. The classic 5 friends theory has legs to it — those people’s beliefs,attitude and approach to what is possible in life will shape yours. This is particularly hard if none of your current challenges resonate with your friends because they work in secure, traditional roles. Find or build communities that align with your values and way of living Expect your friendship group to change or grow in a very different direction.
Get a coach to support you on the rocky journey. Learning to make decisions with limited data, jump into the unknown and generally make big changes to the way you work is a norm when creating. This ‘full’ headspace can affect both our personal and professional life — creating the time to really reflect on your decisions, help your move through your fears or other blocks (e.g.limiting beliefs that prevent you from selling, or changing strategy) — is super helpful. You don’t have to fork out £££’s for a coach — coaches-in-training are often free or cheap, and most accelerator /entrepreneurship programmes often exec coaching.
Mentors are everywhere. And you need them, so build or join a network! There is so much to learn about every aspect of the business, and it helps to have a network of people you can ask for help. Find communities of likeminds, go and meet people (build friendships), add value as much as you can first, and don’t be afraid to ask someone for a short call. People like to help. Additionally, books are great mentors — read as much as you can!
When you know how to do something, you become a teacher or mentor. It took me a while to get past imposter syndrome and realise that even though I had only run a business for 6 months +, I had already learnt a host of valuable lessons about running events, building an audience, and and MVPs. Embrace your lessons and offer to help out others on their journey as much as you can.
Whatever happens, keep your boundaries. The classic entrepreneurship challenge is burnout, and it is very very common. Being a highly driven, optimistic and naive founder, I fell for it too and essentially prioritised most things in my life that were not work, and my bedroom became more of a stressful solo workplace than a room to rest. These blurry lines meant that I never had time to fully rest — on the evenings, on the weekend because my bedroom just reminded me of work, I was working during these times and if I wasn’t I felt guilty about it. Define when you won’t be working, boundary that time, manage others expectations and ensure you continue to have fun with friends. T
Put on your project manager hat, and ensure you create systems to stop everything falling through the cracks as there will be a lot of moving parts that need to coordinate.
Have fun & play — that is where the ideas will come. Similar to #7, when you create moments oustude ‘task mode’ you will feel nourished, re-booted and it will also create the space for your brain to process decisions and new ideas.
Find a stress-relieving activity — this can be something playful, but ideally it involves moving your body. Own bodies store the stress, which there can be a lot of, so a consistent exercise routine will help reduce the impact of this, and clear your mind so you can focus.
Invest long-term — the good gigs can take time. People don’t buy overnight — they need to be exposed for a while, trust you and the product. Plants lots of seeds, making your relationships memorable by being likeable/charismatic and useful, and stay in touch.
You are a <insert role/label> when you spend your days doing something, not when the world gives you an award to say you are that. Let yourself own the identity even if you don’t feel good enough. It took me over six months to own the labels of a coach trainer and dancer even though I did all three at least every week or two.
Talk about and build your idea in public — this creates accountability for you to deliver something, makes it real (it is out there in the world and not just in your head), you get feedback (directly or indirectly) and it exposes your ideas to potential clients/customers.
Learning to speak well in public, write well and talk to new people are three of the most important skills you need to communicate your ideas to the world and get people excited. Skill up and practice wherever you can — that is how you improve. It took me at least 3 months of running events before I learnt to be okay with the nerves involved in public speaking, especially.
Word of mouth marketing is the biggest compliment you can get. Be so great (and unconventional /novel) that they want to talk about you.
Always have a MVP or experimental mentality. When building anything there are so many assumptions involved in the process. The most important element is testing to understand why things work or not, nt building the perfect solution. Build something that is good enough and refine later. When I started Trigger I didn’t have time to create a website so I created a basic logo, Facebook page, eventbrite page and conversation cards (on MS word!). Running the first event cost me £0 and made me profit, but more importantly I got a tonne of feedback that helped me refine the product, and created momentum and an experience that others talked about (which is why the numbers doubled for the next events).
Say yes a lot, especially at first. Planting seeds and being open minded helps a lot. Most opportunities come through the most amazing series of circumstances (you have to have met person A to be invited to event B, where you heard about idea C, which led you to be introduced to person D who informed you about E opportunity).
Be in the world (as my friend Josh says). Show up to things, talk to real people. Similar to ‘saying yes’ and ‘building in public’ this is a reminder that what you browse online is a tiny portion of what is happening in the real world. People are the best sources of opportunities, and experiencing things in the world will shape you way more than simply consuming information online.
Tell people about what problem you are trying to solve / the challenges you have right now. You’ll be surprised how often they can direct you to tools, people or other resources etc. You will feel serendipity everywhere.
Rejection is not always sign that you or your idea sucks. Rejection can look like: no replies to emails, clients saying no. Get curious about the ‘no’— ask for specific feedback on what is stopping them. Maybe you need to explain what value you offer better, maybe it just isn’t the right time for them, or maybe it is the price point.
What is your value proposition? Get clear on why someone should care about the idea — what problem/pain point is it solving or what goal will it help people reach? Talk about those things.
Be prepared for your family and friends to not always approve or understand. They often care about you so much that they don’t want to see you stressed, or taking risks that might hinder your opportunities in life. They also likely have a completely different frame of reference ( if they have never started their own thing before) so simply can’t relate.
Identify the important versus urgent tasks. Often we get stuck on completing the urgent tasks and not creating the systems or building the strategy that will help in the long run. As a solo founder I ended up prioritising replying to people and driving ticket sales more than looking at different ways to ru my business model for the long-term. Nowadays I time-block deep work time (for when my energy is highest), batch related tasks and have different segments of my to-do list which determine what is a deep work/ important task (e.g. writing content) and what is just going to give me a dopamine hit (replying to an email or social media comment). Additionally, I colour code my calendar so I can see what tasks I am spending time on and where.
Be careful giving about equity away— people who believe in you and your ideas will want to help you, which is great. But don’t give away your equity too early. Most people will be happy to simply give back and support you as a mentor for free.
Inspiration can be engineered when you run out of it. If you’re running low on ideas or challenged solving a problem try one of these: change context (work from a new setting), go for a walk through nature, a built up urban area, attend a gallery or something you have been curious about for a while, listen to an podcast/read a book, or do a physical activity (sport or even cleaning).
Create a weekly reflection ritual with questions that ask you about how you’re feeling, what your did that you’re proud of, what you learnt, what was challenging. These will help you capture and enjoy the journey but also help you course correct quickly. These are my current questions.
Co-founders or collaborators are super useful for creating & strategic thinking, accountability & support and getting you out of your head. If you are a solo founder (like I am), use your friends and mentors.
Create a story / mission that invites people to be part of a wider change. Don’t just talk about your product/service. With Trigger the story was about rejecting the idea that we are our job labels, everyone is craving meaningful conversations and that they should be more about changing the way we see the world.
Look after your wellbeing. Moving out of my home office into a co-working space was one of the most important ways I improved my mental health and wellbeing. It gave me better boundaries, less stress at home, better time off and rest.
Remember it a marathon, and some days or week will through more obstacles than success at you. Keep going, embrace all the feelings so they can release and don’t take it too personally.

☕ If you enjoyed reading this list and want to support my writing I would love a coffee!

👉 https://www.buymeacoffee.com/30Listsof30 👈

Your support will help me fund my PhD starting in October 2021 at the School of Design Engineering, Imperial College, London. The subject: Human Connection & Conversation Design. This research lab > interactionfoundry.com

Want To Read More Lists?

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

List #23: 30 Lessons from 5+ Years of Entrepreneurship and Creating

30 Lists of 30 to Celebrate my 30th Birthday

The What & Why Behind This Project:

So, Back to Lists…

List #23: 30 Lessons from 5+ Years of Entrepreneurship and Creating

Written by Georgie Nightingall