Maybe there is no "plan"

The perils of perfectionism and not knowing exactly how it has to work

Author

Ross Stevenson
January 6th, 2026

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 TODAY’S THOUGHTS ☠️

Hey there 👋,

It’s 2026, we made it - go us!

Each year we go through in this century surpasses when all those popular sci-fi stories were set in films released in the 80’s and 90’s. I’m still waiting for my hoverboard and self-lacing trainers, btw.

We’ve landed in that weird zone where we move from “I want to relax and eat everything” to “I must become a superhuman and achieve all these things!”

I have a lot of mixed feelings about this time of year.

I’m not one for ‘new year resolutions’ or the ‘new year, new me’ movement. I get the idea and motivations behind them, yet I often question the psychology behind them to accomplish what one really wants.

Saying that, I thought we’d do something different today.

Building a career as an independent creator has not been a linear path, and has required a lot of unconventional choices. This leads to a lot of messages from people asking, “How did you do this?” and “What was your plan?”

I don’t have a straightforward answer.

But today, I’m going to share a little of my own journey and philosophy behind how I got here and having this conversation with you, right now.

Get your tea or beverage of choice ready 🍵.

We've got lots to discuss!

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 IN THIS DROP 📔

  • Unconventional career advice no one asked for

  • 2026 is the year of storytellers

  • Why most companies’ AI adoption efforts fail the human

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 THE BIG THOUGHT 👀

Maybe There Is No “Plan”

Obama Reaction GIF

Stick with me

It’s the start of another year, and I know many of you will feel some pressure to do something extravagant in the year ahead.

I’m all for that, but aware of the toxic environment it can build.

I’ve covered this extensively over the years, so I’m not going to repeat my views on that today. If you want to tap into those thoughts, find them here and here.

By all measurements, 2025 is a year I certainly don’t want to remember.

Not because my business didn’t do well or anything related to my work. It was all those other things we fear but hope don’t hit us - fear, loss and all that jazz. I had a huge reminder of my mortality in 2025, and to be incredibly open, it terrified me.

This experience, coupled with some other personal challenges have quite rightly challenged how I view the long-term view of ‘having a plan’. There’s a famous Mike Tyson quote that goes: “Everyone has a plan until they get punched in the face”.

I understand that more than I have in my previous 37 years walking around this space.

It’s this time of year that everyone thinks about how they could do better and be better. As I said before, this is admirable.

Over the past 2 - 3 years, as my ‘online profile’ seems to have become more and more visible (no, I will not say internet famous!), I get a lot of questions about how I built my lil business and how I planned all this.

You might be interested in doing this yourself, who knows!

Yet, I’m sure my response will surprise you.

I've never had a "5-year plan".

I rarely have a 5-week one. Yet, I've built a career and way of life that benefits me out of this.

While some are cut out for corporate life, I was not.

You can build a great career with a company. I did that for 15 years. I learned a lot and had success, but that system didn't let me craft the life I wanted. It made me conform to a system that I just didn't work well in.

That led to an incredible amount of friction, which played out in a lot of different ways.

I had a list of fancy job titles with global organisations and with more money than I could spend, but I was never happy. I was doing what I thought I was supposed to do.

About 7 years into my corporate career, I started writing online.

Both on LinkedIn and in what became this newsletter. I had no plan for it. I just knew I enjoyed writing, sharing what I learnt with others and following my curiosity.

Today, over 5,000 people read this newsletter every week, and somehow, nearly 35,000 people follow my words across social media.

Still, I never had a plan for it.

Life is f*ckin messy.

It doesn't happen for you. Instead, you get a constant set of choices you have to make daily, weekly, even hourly. To do this or that based on today's data.

The Future is Tomorrow Morning

From a young age, society puts a stupid amount of pressure on us to figure out big life choices early.

In our early school years, we’re asked to choose the major subjects in which we’ll study so we can progress to higher education. Once we reach higher education, we’re forced to figure out what we might want to do for the rest of our careers.

I mean, pressure, much?

I don’t know who came up with this system.

But, to ask those under 18, “What do you want to do for the rest of your lives?” and “You need to pick the subjects to study to get there now” is crazy.

Most of us are trying to fight our teenage hormones and all the drama that brings whilst juggling the latest popular Netflix shows. 

Do you think we have any idea what we want to do for the rest of our lives at that age?

The truth of the matter is, you don’t need to have it all figured out.

And we commit this same mistake in our careers.

We’re obsessed with knowing the path in and out. It pleases our human brain to have certainty, I get that.

A looong time ago, A former CEO at a retail empire I worked in the L&D team for, dropped this piece of gold in a team email as part of their end of year message

“True happiness beats in your chest. Work out what you like to do best and try to do more of that. Don’t torture yourself pondering the purpose of life. It’s here, it’s now & it won’t last forever, so enjoy it.”

I think about this quote many times throughout every year I’m still kicking around. It’s done more to give me a north star than any “plan”.

You might not believe this, you might think I have some super secret playbook like those social media gurus talk about, but I don’t. I do the best I can where I am in life with what I have (Yes, that’s another quote, see Roosevelt).

I’m not saying don’t have ambitions or things you want to achieve.

Just don’t go insane over building a perfect plan to reach it. Put one foot forward every day, make the best choices based on the data you have and be prepared to adapt when the time demands it.

That’s my best advice.

Tools, ideas and resources

Here’s some stuff to help craft your own life and career philosophy:

Final thoughts

There is no linear yellow brick road to get to any destination.

All we have is chaos, opportunities and choices to make.

So, don't worry about having it all figured out because no one does.

Just make the best choices with what you know today and find some happiness/purpose with the time you have, as it won't last forever.

I'm going to put this one under "non-traditional career advice no one asked for" 😂.

Hopefully, this helps one of you humans out there.

Maybe even you, AI...cos I know you're reading this too.

→ If you’ve found this helpful, please consider sharing it wherever you hang out online, tag me in and share your thoughts.

 👀 ICYMI (In case you missed it!)

  1. Storytelling will be the sexiest skill of 2026. Don’t call it a comeback because it never left, and no AI tool is going to do this for you. The words “storyteller” or “storytelling” were mentioned on earnings calls and investor days 469 times this year. The world’s biggest companies need storytellers, and storytelling is one of our most precious human skills (Bonus: Get my guide to crafting your storytelling powers).

  2. Deloitte discovers that most companies’ AI adoption efforts focus 93% on tech, and only 7% on people. A crazy stat from Deloitte’s CTO, yet not one that surprises me. We’ve seen this before with so many tech implementations. All this FOMO has created panic-driven investment strategies and little thought to how people get value from all those tools.

  3. Your parents probably don’t understand your career, but that’s ok. It’s never been easier to create your own path, and it’s never been more confusing for those in previous generations to understand what you do. I’ve changed through so many definitions of what I do that I now tell people something that’s easier for them to connect with, rather than what I really do. Maybe you’re in the same boat.

  4. Don’t let social media fool you, everyone has a part to play in a AI focussed workplace. Rejoice, fellow humans, an article that focuses on the positives of AI and why being human is still your greatest advantage.

 VIDEO THOUGHTS 💾

Why I’m Conflicted About This NotebookLM Feature

This video answers one of the most popular questions I'm asked in workshops, but I don't feel good about it. At the end of the day, people want help with the tasks they do most often.

For most of the corporate world, that’s creating a lot of slide decks.

So, when I saw that one of my favourite AI tools in NotebookLM released a new feature to create a slide deck from your notebook sources, a tiny piece of me died inside.

But that all changed when I spent a bit of time testing it.

It’s a quick process and, so far, I’ve had very positive results with very little to do on my side.

Let me show you how this works.

Enjoy 😊.

Till next time, you stay classy, learning friend!

PS… If you’re enjoying the newsletter, will you take 4 seconds to forward this edition to a friend? It goes a long way in helping me grow the newsletter (and cut through our industry BS with actionable insights).

And one more thing, I’d love your input on how to make the newsletter even more useful for you!

So please leave a comment with:

  1. Ideas you’d like covered in future editions

  2. Your biggest takeaway from this edition

I read & reply to every single one of them!

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