Logs - Q4 2023
Extracts from my daily writing
27 December 2023
15:14 — there is something magical about train travel. More specifically, writing while traveling by train. Few places where I get into flow better.
26 December 2023
10:05 — I love this time of year. A few days off to completely reset and do nothing. I was slammed with work towards the end of this year and didn’t realize how sleep-deprived I was. After a few days of sleeping in, trail runs in the mountain and taking time away from the laptop, my energy levels are up and I’m feeling excited about writing and tackling big goals in 2024 again.
21 December 2023
08:01 — Thinking of writing a “best of 2023” newsletter.
Similar to the Rest Edition I did in July this year, this would be a curation of:
1. Essays/newsletters: My 5 best articles from the year that’s been. I published 26 newsletters so one every two weeks.
2. My favourites: my favourite “Favourites”. The top quotes, books, essays and photos from 2023.
20 December 2023
11:02 — I’ve been capturing lots of notes over the last few weeks without recording them here. Time to change that.
It’s too easy to jot them down in Apple Notes without going one step further and logging them here. The problem with the lazy route (not logging) is that I forget some of the context and motivation behind the hastily scribbled down note and it’s more difficult to recall the bigger message.
As Naval Ravikant says:
“Inspiration is perishable, act on it immediately.”
10:55 — great quote from Morgan Housel:
“Be careful who you praise and admire. Be careful who you look down upon and wish to avoid becoming.”
The first line feels obvious. What you aim at is close to where you land up at. If you have bad rolemodels, your chances are slim, but if you aim high, you push yourself to greater heights. That type of thing.
The second line is more interesting.
Be careful what you look down on. Might be misinterpreting this, but when I read it, I immediately thought of my internal struggle with sales and promoting myself. For some reason, I did (and probably still do) look down upon on salespeople. I think of a sleazy realtor or second-hand car dealer.
But this year I had to learn to deal with sales and become more comfortable with it. I couldn’t look down on it, because I was doing it myself. If I don’t like being sold to, what does that mean for the people I’m promoting my services to? Had to get comfortable with the fact that I was selling something valuable that could solve a genuine need for them.
20 December 2023
17:17 — love this quote from David Whyte:
“Friendship is a mirror to presence and a testament to forgiveness.”
I’ve been lucky to spend time with close friends this holiday. We used to live together in Johannesburg, but now we are all spread across the world (US, UK, DE, SA) so we only get to see each other for a handful of days a year now.
Realize how important it is to make that time count.
18 December 2023
08:32 — good question for 1-on-1 check-ins with juniors:
"Tell me what you're up to, and how can I help you?"
Like this because it serves two purposes:
Current status update: what are they doing right now, which projects and deliverables are they taking care of. Quick temperature check.
Forward-looking: what takes priority going forward, what is in the pipeline. While reinforcing that they are in the lead and asking how you can support them. Not stepping over them, but enabling them to drive things forward.
08:31 — reading German newspaper clips while I’m in SA (Deutsche Welle has a great email subscription option). Two flies with one swat:
Good way to keep my German sharp. Reading is a good refresher and I’m constantly picking up new words for my vocabulary.
Staying in the loop with current affairs. I’ve taken a step back from following the news constantly (too much information, too little signal), but this light, 5-minute commitment is something I’m comfortable with.
14 December 2023
07:50 — Michael Lewis (Flash Boys) re managing people:
“The best way to manage people, he thought, was to convince them that you were good for their careers. He further believed that the only way to get people to believe that you were good for their careers was actually to be good for their careers.”
Resonate with this.
I always look to promote my junior team members - get them to lead presentations, get them to do the work and get recognition.
11 December 2023
07:31 — book of the week: Cry, The Beloved Country by Alan Paton.
Written in 1948 (on the eve of Apartheid), it portrays the hopes and fears of the diverse people of South Africa. It’s less about us versus them (or black versus white), but more about man against his baser instincts.
A native priest from rural Natal goes searching for his son who hasn’t written back since moving to the ‘big city’ of Johannesburg, a place known for lax morals and the corruption of youths. The priest finds his son but he can’t save him from a life behind bars.
I finished reading this book earlier this year and I was struck by how some of the themes persist to this day, almost 80 years later. South African society has made significant progress since the days of Apartheid, but racial tensions (mostly stirred up by politicians sowing division), corruption and crime continue to plague our beautiful country. Like Paton, I still hope that SA will reach its full potential, despite the issues holding us back and dividing us.
7 December 2023
19:32 — my mom got robbed at knife point on her run in the mountain this morning.
Luckily she is fine and came away unscathed. The thieves only stole her watch. Although she is a bit rattled (naturally), we are very grateful nothing worse happened.
We located her watch on the “Find My” app and tracked it to the Cape Town train station deck — an informal market with a mix of stores selling a range of things, from cheap imported clothes to food to second-hand goods. All for the commuters making their way to work in the city every morning and back home every night.
My mom has been through enough, so I offered to go look for he watch.
I’ve never been on the station deck before and it’s not the safest place at night. Some shady characters hang around there. I went down to the police station to see if one of the police officers would be kind enough to escort me to the station deck to try to locate the watch.
After waiting a bit, one of the undercover (plain clothes) cops came to help me.
We went to the station deck, he made a few enquiries and we located one of the shops that deals in second-hand (often stolen) goods. The shop was closed, but he got us in and there were a bunch of watches, phones and other second-hand goods. I couldn’t see my mom’s watch so I played the alert sound from the “Find My” app.
No sound.
I tried again. Same result. No alert sound played.
We weren’t in luck. Seems like her watch was in another location that was closeby, perhaps another shop a few metres away.
Despite not finding the watch, I was happy for two reasons:
At least I tried to find the watch and made an effort. It would be too easy to just let things slide and write it up to ‘crime is out of control these days, without doing anything about it.
I had a fascinating conversation with the undercover cop.
He says he sympathises with the crooks, they are desperate, but he believes there is always a way out. You can always choose a path that doesn’t involve crime.
He grew up in a shack in a tough neighbourhood run by gangs outside Cape Town. He was raised by a single mother who fell between jobs. Lots of his friends got into trouble with the law. He could easily have slipped into that life as well.
Despite his circumstances, he built a good life. He got an education, made his way up in the police force and started a family. He chose the right path.
“It’s always up to you and your choices in life.”
Inspiring stuff.
5 December 2023
19:26 — interesting observation re managing people.
I absolutely love working with younger people. Great mentoring them and guiding them.
I’m also realizing my limitations. I have become a bottleneck in their workflow. I like giving them assignments and the freedom to approach the projects the way they want. No micro-management. Once they’re done, I like to review their work. But in busy weeks I can’t get around to reviewing their work. So they perform their part and I don’t keep my end of the deal. Not cool.
What gives? Ask them to review each other’s work? Create more time in my schedule for reviewing work?
Sure I’m not the first person that has faced this issue.
07:05 — the best part about working with my current client.
There are no sacred cows. I am encouraged to point out what they are doing wrong and where they can improve.
I don’t have to fear hurting anyone’s feelings or sounding harsh. They want the best solution for the business and that means dealing with uncomfortable truths.
07:01 — so pleased about this note-taking/logging habit.
It’s helping me be more observant. I can spot patterns in my thoughts. I can spin up newsletters quicker (if I want to).
This week I’m writing about my corporate to creator to corporate full circle journey.
Next week I might try my hand at business writing. There are a few notes on consulting and working with clients in here. Never expected I would write about business tips, but here we are. Quite excited about it.
4 December 2023
16:05 — love this quote from Mary Oliver.
“Instructions for living a life: Pay attention. Be astonished. Tell about it.”
It’s as simple as that.
08:07 — reflections on being a creator for 2 years.
I’m slowly but surely moving back into the ‘corporate’ mould.
After giving writing and course creation and online teaching a solid go these last two years, I am spending more time on traditional path projects again because my skills are recognized and rewarded there.
I can earn decent money performing work for insurance clients as a freelance actuary. I am so busy (things are good) that I don’t have as much time for writing and tweeting and drawing.
And it’s fine. I’ve made peace with it.
I have found a mode that works for me.
Looking back at when I started writing online at the end of 2021, I’ve had an interesting journey. I managed to get out of a shitty job. I met incredible people. My eyes opened to the possibilities out there. I learned a bunch of new skills.
I picked up a valuable mindset. Something like looking out for myself. Looking for opportunities. Making sure the things I do are aligned with my values and that I have skin in the game. This can’t be taken away from me.
I also realized how difficult it is to make a life as a ‘creator’. I tried launching a course earlier this year which I had to close because I couldn’t sell enough seats. I’ve made a small amount of money from ghostwriting, selling my self-paced drawing course and mentoring online writers. All cool experiments, but not enough to pay rent and living expenses. There was a period of 3 months where I made more from dog walking than other projects. It was a serious reality check.
My anti-goal (the negative experience I had in my old corporate job) no longer served me. I used that internal anger to quit and find a new path. I used it to build a writing and creating habit. But now that I’m out, there is nothing to fight against anymore.
There is also an element of maturity coming through. While I would still encourage people to try creating and writing and see what comes of it, I also realize not everyone can make it as a solopreneur/creator. I tried and came up short. There are different ways of selling your skills and you need to find the best mix for you.
For now, my mode looks like consulting for the financial rewards and creating for the non-financial benefits — my mental health, leaving a legacy, making an impact, meeting cool people.
I can see it working. While I am passionate about writing, there are aspects of consulting that I really enjoy — building tools and models, working with startups, solving complicated problems. And there are aspects of creator life that I didn’t enjoy — tweeting, doing things for growth. So, as with most things in life, there is nuance and no single path is made for everyone.
Where to from here?
I want to continue writing. It would be too easy to focus purely on consulting.
I want to be in the arena. I recognize that I have valuable views to add to the conversation. What are my reflections on managing people? What am I learning on the consulting projects? What skills can I transfer between the two worlds?
I want to continue this obsevational way of life. I will look back at this moment and be grateful that I captured my thoughts.
If anything, just to help other young people “figure out” how best to dedicate their lives.
3 December 2023
22:12 — really admire my one partner at the consulting firm I joined.
Old friend of mine. Really solid guy.
The thing I admire is that he is unable to get stressed. Exudes calm and confidence. Seems like he always knows things will work out for the best. Not sure how he does it.
Could see him ordering one more glass of champagne while the bar was burning down, knowing that he’ll find the fire extinguisher afterwards and save the day.
1 December 2023
08:10 — don’t panic.
Everything usually works out.
The key is to have the confidence that things will work out and then approach the project knowing you will find the solution eventually.
Basically two roads:
Stressed. Unsure whether the solution for the project is out there. You start panicking, you get anxious. This reduces your problem-solving capacity and you start making mistakes. A vicious circle ensues.
Relaxed. The opposite approach. You trust/know you will find the solution, you will deliver what the client expects, you will crack the problem. Knowing this, you are more relaxed and confident. Your mind is primed to find solutions. You know you will get there given enough time. The ‘knowing it will work out’ becomes a self-fulfilling prophecy in that it actually ‘works out’.
07:15 — main things to solve for a happy life:
Where you want to live. For me this comes down to having access to nature (running, hiking, skiing), with enough opportunities to do things (culture, shows, exhibitions) and seeing my family. Currently lucky enough to split my time between Munich and Cape Town. Ticking the boxes.
The work you want to do. I want to work on things that are meaningful and align with my own values. I like to work on things where I have skin in the game. I like to build things. I want to leave an impact on the world. Current mix of consulting and writing is the right for me at this stage.
Having freedom over your schedule. This has been the biggest thing I’ve designed my life around over the last year. Not being tied to meetings. Not being tied to an employer that can tell me when to be in an office or when to take leave. I am the master of my time. I don’t feel guilty for going on a long weekend or going for a run during the middle of the day or travelling to see my family. I want to impress my clients so I will work hard for them, but I am extremely happy about the fact that my schedule is something I opt into every day.
Health. Physical and mental. The foundation for everything. Having a consistent training schedule, meditating, building in time off, all these things have provided the base from which I could work on challenging things and push myself.
07:02 — thoughts on managing deadlines and designing my life.
I would like to get to a space where I have free time again. This week and, come to think of it, the last few weeks have been demanding from a work perspective. Big deadline yesterday. Another big one next week. And it feels like I’m dropping balls on other clients.
But what about my writing?
I am either in struggling artist/writer mode or I am in all work/no play mode. Sadly these two modes don’t really mix. A better design would be to incorporate both elements and have a smoother ride through life.
The logs help. I can make small notes here and there when I have a moment. What I would really love is to write my newsletter consistently again. Goal/experiment: try to trim down the newsletter. A collection of notes. Something short and brief and viable. Can I be less of a perfectionist?
I suppose this is what makes me put in so many hours for my clients as well.
Will 90% be good enough? I can’t give it my all on all fronts.
28 November 2023
07:52 — something I've been trying to pay more attention to lately.
To be kinder to my younger self while acknowledging how much I needed to grow and have grown since.
I did the best with what I knew back then, like I'm doing the best with what I know now.
Some future version of me will probably think '32 yo John made lots of mistakes'. So be it. This is the never-ending journey of self-improvement.
27 November 2023
08:15 — ran a trail run in Cape Town yesterday.
35km with 2000 metres of elevation in the searing heat. It was brutal.
I fell after 6 kilometres on the contour path heading up to the first big climb for the day. Open hands, blood everywhere, winded, but I decided to continue.
Happy I did. It was truly a beautiful route and the vibe and camaraderie between the trail runners is something special. Couldn’t run as hard after my fall (less confident on the technical downhill parts), but made it my mission to finish.
Eventually I made it to the end. Looked like a soldier returning from behind enemy lines, battered and bruised, but smiling and happy for the experience.
08:02 — types of work.
Picking up two broad types of jobs in the consulting work I’m doing:
Either you come in for a specific job spec, where the requirements are clearly defined and easy to test. The client knows what they want. E.g. perform an audit on a life insurance company. There is a report at the end, they expect you to perform certain test, it’s relatively straightforward to check if you did your job.
Or you come in and the client doesn’t know what they want. This is often more difficult but could also be more rewarding. You can have a bigger impact. You can guide the client. This work is also paid better because the client knows they have a problem but they don’t know what the solution looks like. E.g. redesigning the entire product offering or revamping the company’s business model.
08:01 — back in the game after a week of health issues. First time in a long time I’ve been that sick. Good to hit the reset button. Feeling energetic again.
24 November 2023
19:05 — didn’t buy anything today. Take that consumerism.
23 November 2023
08:01 — great quote on the life of a creator.
“Not knowing what you want to be—reinventing yourself every morning; not being a noun, but being a verb; moving in life, not being fixed in life—is a privilege. And though it’s a difficult life sometimes, don’t feel bad about not knowing. It’s a wonderful thing.” — Stephen Fry
Also see these two paths before me.
Being comfortable with uncertainty can lead to the greatest growth and joy in life.
22 November 2023
18:05 — reflection on reflections.
Some of my thoughts sound quite harsh, down-hearted even. Especially with the stress from client work. Important that I also acknowledge how privileged I am to have so much work. Earlier this year that wasn’t the case. I was sending out cold emails, setting up coffees, making connections on LinkedIn, cosying up to people at conferences. I hated this. None of it really worked.
Eventually, I turned the corner and some clients came my way through word of mouth. Now I’m sitting in a better position financially. The next step would be to still carve out time for creativity in between all the craziness.
17:25 — on my writing future.
Strange feeling that my writing is dying. Maybe it’s just this week, not feeling great health-wise and I’m buried under client work, but there has been a longer slide since around August.
I’ve lost a connection with my ‘why’ for writing.
It used to be spurred by getting out of corporate, doing something on my own terms, breaking free, getting autonomy. I’ve achieved all these things. So that fire is dead. It no longer motivates me.
Time to pivot and take my readers with me.
Options for more material:
Writing curations e.g. Sam Harris’s best podcasts or a summary of The Bear or why Stutz is an important movie for creators
Interviewing people e.g. other writers, businesspeople, creators, people I bump into on the street.
Writing about business. Explaining my approach to my consulting work. What I’m trying to do. Lessons I’m learning. Thoughts about managing/coaching people.
Think it could be fun. Will I be able to shed my old skin?
17:05 — thoughts on falling sick.
Back from the dead. Endured a 2-day stomach bug from hell. Felt like my whole body was purged. I couldn’t eat anything, just moved between the bed and the loo, binged audiobooks, drank a ton of electrolytes and rolled around with muscle cramps at night. Good to be on the other side.
As the saying goes:
“A healthy man wants many things, a sick man only wants one.”
Wonder if I can future-proof myself against this. Been eating out more in Cape Town and also not sticking to my ‘no drinks during the week’ rule. Since I want to catch up with my family and childhood/university friends, my life is inevitably more ‘social’ when I’m here. Been surprisingly healthy this year just by cutting down on alcohol and eating cleaner. Good wake-up call.
But even with good habits, our bodies will shut down from time to time.
Maybe this was more stress-related. Things are mad with client work. I might have stretched myself too thin. Under a lot of pressure to deliver. Maybe this was my body’s way of forcing a reset after going at full tilt the last few months.
Silver lining: made a dent in Ben-Hur.
18 November 2023
16:45 — on the importance of rest.
It’s Saturday afternoon after an intense week of work — kicked off a project with a new client, had multiple flights & meetings and hosted a creativity workshop for 30 students.
Sometimes it’s good to acknowledge that my energy levels aren’t unlimited. Sitting at the laptop today, I’m trying to work without making progress.
Perhaps it’s time to get up, go for a run and come back refreshed tomorrow.
Reminder: you need to switch off to switch on.
16:40 — on the value of good service.
The company I am consulting too has a relatively straightforward product. What makes them different is their commitment to good service. They want to serve the hell out of their customers. 24/7 availability, quick responses in emergencies, fast settlement and payments.
Since this isn’t standard in their industry, they outshine their competitors by just doing the basics right.
16:29 — hard truth via Readwise today:
“The unvarnished truth is that almost all the people you meet feel themselves superior to you in some way, and a sure way to their hearts is to let them realize in some subtle way that you recognize their importance, and recognize it sincerely.” — Dale Carnegie
17 November 2023
18:40 — Speak your truth. Don’t let things slide.
In my previous job, I was hung out to dry on one of our projects. Despite doing a great job, my manager and I were used as scapegoats for the failure of the project.
This hurt.
What hurt even more was the regret I felt for not defending our case when we were being wrongfully accused.
I replayed that scene in my head 50 times. It ate away at my soul.
The pain from this hardened my resolve to never let this happen again. I promised myself, from then on I would stand up for myself. I would call out things that didn’t sit right with me. I would try to control the narrative.
08:21 — silver linings reframe.
I caught up with my old manager this week. Good guy.
I told him about the consulting work I’m doing now and that, while I’m thoroughly enjoying the autonomy that comes from being self-employed, some of the projects are not as fun as others.
He advised me to look for the positives in every piece of work.
You can always learn something new. No matter how boring the work appears to be, there will be something you don’t know yet.
What’s more, you can pride yourself on your attitude. Pitching up with focus and energy no matter what. People value that consistency.
16 November 2023
07:08 — extract from my guided meditation (Waking Up) this morning:
“We all spend a lot of time thinking about ourselves, how we appear to others, who we are, in our lives and in the world, about whether we are the person we want to be, expected to be. But notice that this is who you are in this moment. You are precisely this experience. This moment of hearing. This moment of seeing. See if you can drop all of your ideas about yourself and sink into this moment of practice. There’s always just this, whatever else seems to be happening.” — Sam Harris
Good reminder (“wake-up” call) for me. I am faced with various client calls and presentations today. My mind is preoccupied. My thoughts are racing to the future - meetings this afternoon. What will they think of my work? Will I impress them? Good to take notice. To take a step back. To acknowledge this moment as well.
07:06 — extract from a talk between David Whyte (the writer and poet) and Sam Harris (philosopher, writer, meditation guy) where they compared travel (or a pilgrimage) to conversation.
“No one survives a real conversation if you’re sincere. The person that arrives afterwards is never the person that began in the first place.”
I like this. A conversation has the power to transform, give you new insights, challenge old views, and provide new information. You are richer for the experience.
15 November 2023
18:16 — reflection on doing sales calls earlier this month.
Instead of pitching your product and all its wonderful bells and whistles, it’s important to ask the client what they want to achieve.
What transformation are you looking for?
What pain point are you trying to solve for?
Then show how your product can solve this for them.
Ask questions, reflect, relate.
Don’t bombard them with features and benefits.
You want them to feel like they ‘bought’ the product, not that you ‘sold’ them the product. Empower them, don’t sell to them.
18:05 — started working on a new client today. Might write more business lessons going forward. Some of them are also life lessons.
Learnings today:
Leave ego at the door. Make the best decision for the company. Challenge people, don’t respect someone’s title too much. The best ideas and best solutions for the customer are all that matters.
Stories sell. Let the real life stories work their magic. People care more about how the product will help them in a specific situation they can relate to. They can connect better with a client testimonial, e.g. a helicopter evacuation in an emergency, than listing all the benefits.
07:06 — I spoke to one of my friends about Ayn Rand’s The Fountainhead over dinner yesterday. He was raving about the book and her philosophy of Objectivism.
I haven’t read her work yet, but found it interesting that one of her core tenets is that people should be the best versions of themselves in order to serve humanity in the highest way.
I wrote about something similar in Live and Let Live.
For a long time, I was projecting onto others. I didn’t have my own thing. I wanted to fix things for other people.
Now that I am happy with my work setup and creative setup, I feel like I have more empathy for others, and being a better partner and friend for them.
There are many roads to Rome and many ways of being.
If you live (find your thing), then you can let live.
14 November 2023
08:31 — From the coaching sessions I did earlier this year, it became clear that I am attracted to work that has to do with humans, interpersonal skills, creativity, building things and leaving a mark.
Humans. Self-improvement, meditation, mindfulness, listening during conversation, being a good partner, being a good friend, being a good manager. All these things matter. There is so much to learn. What matters isn’t necessarily what you did for someone, but how you made them feel.
Building things. Ever since I was young, I built things… model airplanes, bridges, sand castles. And then later tools for our company, interactive models, dashboards. Still later I made things like my website, essays and sketches. I like showing what I did. I like pointing to something that’s mine. I want to leave a mark and somehow contribute to the world.
13 November 2023
08:01 — idea for a writing community:
Monthly buy-in e.g. $100 a month to be part of a Writers Who Support Each Other group. Money goes to the people organizing to acknowledge their time and effort to keep the community going. The buy-in also helps to motivate students. Like going to a gym - you’re more committed when you pay for something.
One weekly community call led by a 'mentor' at a fixed time. Time to talk through wins and challenges and go into breakout rooms to write or get feedback.
Additional guest speakers/lectures/workshops here and there.
Extras: coaching, live editing, one-on-one sparring.
Quite bullish about this. I’ve been looking for a way to find more alignment between the things I do for money and the things I am passionate about. Can see it as a small bet.
10 November 2023
20:10 — running list of my favourite books so far this year:
East of Eden by John Steinbeck (1952). Damn, this is good. Packed with life lessons, quotes and philosophy. Steinbeck’s story and characters share his view on life and how to live it, but also convey his questions and uncertainties. Stong, yet vulnerable.
Ben-Hur by Lew Wallace (1880). Currently reading this epic and I’m blown away. The story of the Christ, told as a novel, which follows the life of a Jewish gladiator. Some overlap with the Bible, but told more matter-of-factly.
The Unbearable Lightness of Being by Milan Kundera (1984). Find new wisdom from this book (via notes from Readwise) every day.
9 November 2023
23:20 — I got a couple of questions from a reader who read my Luck Surface Area article. I tried to answer him as forthrightly as possible.
What feedback have you gotten by writing online?
Personal: readers have reached out and thanked me for sharing my journey because they resonated with my message and could identify with the challenges I was facing. Some of them have also been motivated to start writing and take more risks which is wonderful. Good reminder that we don't write in isolation. Our words can provide solace for others.
Business/tactical: my readers have pointed out which essays they like and what they'd like to read more about. They've also pointed out what they'd like to learn from me (e.g. how to use procreate) and this feedback led to product ideas (small bets).
How do you navigate the line between humility and self-promotion?
I try to remind myself that I have a duty to share my work with the world because it can help people (like the examples show above). By keeping all my ideas and notes to myself, out of fear or out of too much humility, I would not be contributing to the greater good of society, I would not be making a positive impact on the world.
When I am unsure about posting something (maybe a recent win or success), I listen to my gut instinct and try to determine whether I'm doing this to show off (stroking the ego) or if the motivation is less selfish and could potentially inspire others. Not always easy, but important to train that internal barometer.
I like these questions because they keep the writer (me) honest. Every sentence I put in an essay needs to stand its ground when confronted with a question. There's no room for filler sentences and fluff.
23:11 — when jealousy rears its ugly head, remember to focus on your own path and your own vision.
The last few weeks have been non-stop with client work.
I am grateful for it (I experienced the reverse earlier this year - having no work coming in sucks) but I'm also sad because I haven’t been able to write and create as much as I would like to.
I just finished Write of Passage cohort 11 and I saw other writers composing beautiful essays. It’s wonderful to see the magic that happens when people fully devote themselves to their craft and passion.
While some part of me wished I could also do that, I had to remind myself that I was trying to solve a different problem - managing a number of consulting projects and trying to grow my customer base. Something that could help me in the long term, even though it was eating into my creative outputs in the short term.
I’m happy for my writing peers and I’m grateful for their inspiring essays. I’m confident that my writing days will still come.
8 November 2023
17:15 — training regime for the next month in Cape Town.
Focusing on 4 things:
Running: the sport I enjoy the most and still perform relatively well at. Get the aerobic and anaerobic fitness plus the mental benefits of getting outside and alone time.
Swimming: supports the running. Also lower impact on the joints. Good alternative.
Yoga: supports the running. Prevents injuries. Flexibility is probably my weakest area. Good to get down and work on the
Golf on weekends: purely for fun and spending time with my dad. Will see it as that as well so I don’t get too upset if I play poorly.
What am I cutting for now?
Weights: got back into it this year. The benefits have been significant. Looking and feeling better, but also seeing gains in running endurance. Pausing for a month while focusing on mobility.
Cycling: takes a significant amount of time. Can’t manage this and golf.
7 November 2023
08:55 — the last few months have been a good time for reflection. Especially on where I want to take my writing.
When I started writing, it was an escape. It was a place where I could express my ideas. Something I wasn’t encouraged to do in my corporate job - all product updates were put on hold for 2 years. In a way, the writing was a middle finger to the people holding me back. Like - “look at what you’re missing out on by not using me to my full ability”. I had strong antimodels:
"People focus on role models; it is more effective to find antimodels - people you don't want to resemble when you grow up." Nassim Nicholas Taleb
This motivation spurred me on for a long time. The writing helped me quit and create a work-life setup where I had more autonomy. Where I could build things and also work from anywhere at any time.
But, after this, the anti-goal lost its power. It had served its purpose. I was no longer writing “against” something. I no longer had to get out of a bad situation. I was out - it was time to move on and seek a higher purpose.
It was almost like working out intensely after going through a breakout. You hit the gym two days a week, crush your runs, and get in your best shape. All to show your ex what they’re missing out on. This motivation lasts for a while, but it’s not sustainable. Eventually, you forget about your ex, life moves on. Only internal motivation (working out because it’s good for you) will keep you going.
And I think that’s where I am now. I write because I know it’s good for me. It keeps me calm and it generates opportunities. What more do I want.
08:45 — hosted a creativity workshop for the first time in 4 months yesterday. Blown away by the participation. There were 16 people on the call at one point.
Started off a bit rusty, but got into the flow eventually. Took them through the benefits of adding illustrations and showed them my A/B technique for illustrating. The picture (like this example) needs to show some transformation — before vs. after, wrong vs. right, old idea vs. new insight.
One of the students asked a question that stood out to me. She wanted to know how to get started. She uses a lot of visual language in her talks with clients, but she can never capture the words in picture form. I like the question because it drives at the heart of the creative process.
In a way, drawing is very similar to writing:
Draw first, then evaluate your picture afterwards. These are two separate processes. Just like writing, you need to write first, then edit. You can’t do both at the same time. These engage two different parts of the brain.
Draw from conversation. Explaining your key idea to others and talking out loud is a great hack to generate ideas. We express ourselves most naturally in conversation. Use this for writing and drawing. “I want to illustrate a person being transformed by a positive comment, ah ok, yeah, maybe some animal that goes through an evolution, how about a caterpillar into a butterfly?”
Get feedback. An essay that has been through a few rounds of feedback always lands better than the original draft. You can see where people are getting confused or stuck or which parts excite them. The same goes for drawing. Show your picture to people - do they ‘get’ what the picture is trying to say? Does it land immediately?
Try to create a transformation in the image using the A/B technique I mentioned above. After someone reads your essay, you hope that your words left a mark and created a transformation in your reader. Did they learn something new? Was there a call to action? A new habit they should incorporate and how this will change their life? Try to do the same with drawing. Show that change.
08:33 — getting back into cold water swimming now that we’re in Cape Town. The ocean is usually an icy 8-12 degrees Celsius.
Starting to recognize a clear pattern in my mind each time. Before: “Damn, this is going to hurt, I should’ve stayed in bed.” First 3 minutes: “Wow, this is really cold, must be colder than last time, every little skin cell is begging me to get out.” After 3 minutes: “Ok, I can actually do this, it’s not that bad, this actually feels good in a weird way. Let’s chat to people.” Afterwards: “Boom. Time to conquer the day. Can’t believe I didn’t want to get in initially. Wim Hoff eat your heart out.”
Wonder if this goes for other difficult things. It’s only scary until you’ve done it. Sam Harris says something similar (need to find the exact quote) - our perceived pain or our fear of an activity usually leads to more discomfort than the actual pain during the experience. This is the value of meditation - to recognize that our thoughts (which are not real, just made-up little things that float through our head) have a lot of sway over real things.
6 November 2023
08:10 — saw this quote this morning which made me think back to a younger me, the old colleague I spoke to last week and many people who are still doing work that doesn’t bring out the best of their abilities.
“At the end of the day, too many potentially highly productive individuals are underutilized, to their detriment and to the loss of society as a whole.” — Tyler Cowen and Daniel Gross, Talent
I do see this changing with more people questioning the work they do and whether this work (i) matters and (ii) brings the best out of them.
As
Paul Millerd
says in the Pathless Path:
“On the pathless path, my conception expanded, and I was able to see the truth: that most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen.”
07:48 — I’m 10 days into logging. I’m really enjoying the practice. Here are some of the benefits I’m seeing so far:
Info capture +. It’s a more polished version of information capture. Where I used to take random little notes in Google Docs or on my phone, these published notes are of a higher standard.
Daily writing habit +. I did Morning Pages for a while at the end of 2021 and the start of 2022. The practice was useful but I eventually lost steam. I also wrote a lot of things that I didn’t capture or publish properly. This is like Morning Pages, but you curate the best parts for future use. Less waste.
Mindfulness. I capture my thoughts as they occur. I am more observant. Every conversation, every interaction, every random daydream has value and can potentially be used in a future essay.
Low stakes. I am still publishing, but there’s less pressure to create a clean, reviewed newsletter. I can get something out in 5-10 minutes (newsletters take 2-6 hours).
Less self-rejection. “Ooh, I don’t know how this will land with people, maybe I shouldn’t write this.” Enough of that. I want to speak my latent convictions. I want to share my thoughts instead of silencing myself. This has given me confidence. I’m less scared of the page.
Patterns. Looking back over time, I hope to see the golden threads and patterns in my writing. While I started off writing about the creator economy, I’m not tied to this. I am curious to see how my interests evolve real-time.
No rules. Logs can be any length, they don’t need titles, they can be little fragments of thoughts or longer streams of consciousness. It’s like a virtual scrapbook that you can design however you like.
5 November 2023
17:04 — Earlier this week I joined a call with other writers who want to write fearlessly without a pseudonym. While I’ve had overwhelming support for my writing, I’ve also received some criticism from people whose opinions I respect. This knocked my confidence a bit.
Speaking to others has been instrumental in getting back on the horse.
I tried to capture a few strategies that we spoke about:
The Glass Castle technique. In the book, the author Jeanette Wells only states the facts (e.g. my parents couldn’t provide food that night) without emotion and lets the reader fill in the blanks (she had a rough upbringing).
If you are writing about someone, try to have a conversation with that person you're writing about beforehand. The question is if you can still publish afterwards.
Get out of the fish bowl. Step away and see the situation from a different perspective. It’s often
Write from a place of love. Like Matthew McConaughey does in Greenlights when describing his parents. Mention their shortcomings, but also what they did well. This is more balanced.
Use a pseudonym if that enables you.
Change names and places if that helps.
Try fiction and fables. Unless your reality is truer or more honest than fiction.
Write logs - little snippets that aren't sent out via email, but are only posted on your website. At least then you are not disappointing yourself by silencing yourself.
Use your feedback partners. Write the essay, and let your writing friends figure out how best to package it. Maybe there’s a way where everyone wins — there’s less backlash than expected and you help others by sharing your perspective.
Benefits of sharing our stories:
Healing. Speaking our truth can let the poison out. It can prevent other potentially harmful activities.
You can be a voice for others. We aren't in this alone. Other people can find solace in our stories.
We can get closer to our loved ones. First, we have to go down one mountain (get the issue out in the open) in order to climb up a higher peak (form a closer bond) afterwards.
4 November 2023
13:03 — Write of Passage cohort 11 highlights.
It was another special 5 weeks. At the start, I had doubts about my “why” for writing, but thanks to working with the students and seeing their passion & energy, my inner desire to write reappeared. Very grateful for the experience and all the conversations I had along the way.
Best bits:
Writing fearlessly without a pseudonym. An interest group for people who want to share their stories without compromising themselves or their loved ones. A tricky balancing act — either you write from the heart (which opens the door to backlash) or you write safe essays that don’t challenge you (which are bland and don’t benefit anyone).
Met some great new writers in my mentor groups. Being around people who take the craft seriously inspired me to get back on the horse.
Got more clued up on Substack. Really enjoy this platform and its built-in social network.
Built new writing habits. I didn’t publish as much as I wanted to, but I’ve been loving the daily cadence of logging.
3 November 2023
19:36 — Spoke to an old colleague of mine today. Smart guy. He’s done a lot at the company but feels like he’s reaching a ceiling. Lack of upward movement. The projects are no longer as motivating as they used to be.
He enjoys writing (even won prizes for creative writing in the past) and is dipping his toes in it again.
We spoke about my journey out of corporate. Writing has been the driving force behind my transformation. I haven’t made quit-my-job money from it. Far from it. But writing emboldened me. It gave me the confidence to try things alone. I started ghostwriting. I did a few consulting projects. I started mentoring and teaching. These projects allowed me to quit my job.
Although I haven’t monetized my writing (and maybe never will), the practice is foundational to my success. It generates opportunities. It’s genuinely good for me (and my mental health).
Sometimes the universe gives you a nudge. It says, “you can do more with your life than sitting through these mindless meetings pretending to be interested, you have more to give, don’t deny yourself, don’t deny others.”
Listen to that nudge.
18:31 — I’ve been self-employed for 307 days today. 31 December 2023 was my last day of formal employment. I plan to never go back.
Someone asked me about my biggest takeaways so far. Wrote this down:
Sales. I had to reframe what promotion meant to me. Coming from a non-sales background, I used to have an aversion to promoting myself. Instead of seeing myself as a sleazy salesperson, I had to believe in the value I could bring to potential customers.
Variability. I had to become comfortable with unpredictable income. Some months were great, other months were quiet. Coming from a stable salary (the monthly shot in the arm), the lean months were very tough. I suppose I had what people a ‘scarcity mindset’ — I didn’t know where the next cash would come from. I worked through it. This helped me explore my edges (how far I can be pushed and still be OK) and priorities (what’s really important to me).
Alignment. I feel more motivated. When you land a project, there is nothing (or no one) to hide behind, you either do a good job or don't get future business and recommendations. Enjoy the higher stakes.
2 November 2023
10:30 — back to East of Eden and Adam’s question on how his sons will grow up (logged on 31 Oct 2023). Our expectations of people can have a profound impact on their performance.
Saying “I like how hard you work” invariably translates into that person working hard because they want to live up to that idea you have of them.
This is the difference between a manager and a coach:
A manager seeks to get the most out of you and your current abilities, assigning tasks they know you can do.
A coach looks to develop you and inspires you to be your best, seeing your future potential.
Thanks to David Shepherd for adding this POV.
10:06 — thanks to
Wes Lambert
for reminding me to measure my worth by my inputs instead of my outputs.
After publishing consistently (almost every week) for 8 months this year, I fell off the writing wagon (big time), with only one post published in September and another one in October.
This coincided with the time I was supposed to mentor Write of Passage students about online writing. I felt like a fraud. How could I champion the benefits of writing if I wasn’t writing myself? How could I tell others to write weekly if I was avoiding the page?
I shared this with Wes. He sat there, held his chin, looked up to the ceiling, and asked me why I was measuring my worth based on my writing streak, an output from the process. I was taking time to work on myself and my business, reconnect with my “why”, and rebuild my desire to write, all important inputs in the process.
As Robert Louis Stevenson says:
"Don't judge each day by the harvest you reap but by the seeds that you plant."
1 November 2023
17:51 — finished two months of coaching yesterday. Some thoughts on the experience.
When I started I was: low on confidence, fresh off another consulting deal falling through, and struggling with feedback about my writing.
Ended with: a kinder, lighter attitude towards myself, and a number of useful reframes about my situation.
Each session started off cagey. My coach would ask me what I wanted to talk about, I would look at my notes, suggest a few topics and start putting up my defences. It felt like she was trying to crack a nut that didn’t want to crack. Eventually, through some choice questions, I started opening up. I would go on rants and pour my heart out. It felt good. The dam wall was breaking.
Reframes:
I am disappointing myself in order not to disappoint others. By not manifesting what I want to do, I am trying to fit into what others (my parents, society etc) expect of me.
As a self-employed consultant, I need to promote my work in order to get clients. Problem is I have an aversion to sales. Maybe I’m too proud, maybe I’m too scared of rejection. Instead of seeing myself as a sleazy salesperson, I should consider the value I can bring to potential customers. I can genuinely help them.
By being scared of the opinions of a few readers who don’t buy into my writing, I am silencing myself and not being a mouthpiece for the readers that actually value my message. Why try to write for the whole world (including my detractors) when there is a subset of people (my true fans) that values my work?
00:15 — what does my content diet look like lately? I am subscribed to 50 (and counting) Substacks and a bunch more newsletters on other platforms. I scroll Instagram/Twitter during breaks. I listen to one podcast (sporadically) - Making Sense by Sam Harris. I watch a YouTube video now and then.
Mostly, I just read books. 28 books so far this year. This is at the top of my content pyramid (or should it be bottom - like the foundation?).
Can I be more intentional with my consumption? Especially my engagement with newsletters and other writers. I like what
Elle Griffin
does every morning — 2 hours for writing and 30 minutes for reading & commenting on newsletters. Solid habit. Something to strive for.
31 October 2023
16:37 — I often think back to this exchange in East of Eden.
Adam, father to Aron and Cal, speaks about his sons to his housekeeper, Lee. Their mother abandoned the family when they were young and the father wonders whose character traits they will inherit.
"[Adam:] But I would like to know what kind of blood is in my boys. When they grow up—won’t I be looking for something in them?”
“[Lee:] Yes, you will. And I will warn you now that not their blood but your suspicion might build evil in them. They will be what you expect of them.”
How often do our worst fears manifest because of obsessing over them? Wouldn’t it be better to imagine a positive outcome?
Like Shakespeare said, “There is nothing either good or bad, but thinking makes it so.”
16:09 — on the question of whether you should charge for your writing. I give subscribers the option to “upgrade to paid”. I never considered monetizing my writing, but I also acknowledge (and am grateful for) the subscribers who derive value from my newsletter and want to support me financially. The same newsletter goes out to all subscribers (and I hope this will never change), but those who wish to become paying members (patrons) have the option to do so.
30 October 2023
10:31 — received this vignette from
James Bailey
today. Saving it here to come back to. This is a great lens through which to judge every decision in life - is this serving the highest expression of your individuality?
Behind each face there is a unique world that no one else can see. This is the mystery of individuality. The shape of each soul is different. No one else feels your life as you do. No one else sees or hears the world as you do.
The creation of the individual is a divine masterpiece. We were dreamed for a long time before we were born. Our souls, minds, and hearts fashioned in the divine imagination. Such care and attention went into the creation of each person. Given the uniqueness of each of us, it should not be surprising that one of the greatest challenges is to inhabit our own individuality and to discover which life-form best expresses it. — John O’Donohue
27 October 2023
12:29 — “Logs” inspired by
Michael Dean
who describes his as follows:
“Here’s a changelog of my consciousness. Starting in December of 2021, I decided to capture my fleeting thoughts in prose and publish them to my site.”
You can see all his logs here: https://www.michaeldean.site/p/logs
12:25 — on speaking your truth and not hiding in the shadows.
“Speak your latent conviction… Else tomorrow a stranger will say with masterly good sense precisely what we have thought and felt all the time, and we shall be forced to take with shame your opinion from another.” — Ralph Waldo Emerson
When you think of something but don’t have the guts to write about it. Only to see someone else share the same sentiment a short while later. Why hold back? What are you scared of? (questions for the guy in the mirror)
12:10 — cover photo. Soiernsee, Bavaria. What a magical place. Swam in the lake (stayed in for 30 seconds tops) and spent the night in the local Hütte.
