Exhaustion, privilege and proliferation. A reflection on 2018–2021

As I set out to write a reflection on Timo's recent Product Hunt launch, I was struck by how freeing it was. Instead I found myself writing this. A reflection on the last three years. The two things—Timo and my life—being so tightly interwoven. The simple act of announcing that the new version had arrived gave me great comfort and a sense of the opportunity that lies ahead.

The past three years have been intense.

When we launched the first version of Timo on Product Hunt in August 2018, I don't think we ever imagined that we would be working on it so long afterwards. The initial version was a toy. A weekend project for fun, and a learning exercise. What did it mean to ship your own project?

After the launch we hit pause. Instead of continuing work, I set off on another adventure. I founded a company, Byozo, and created a productivity methodology to identify the work that gives you the best effort to impact ratio. In turn, I signed an exclusivity agreement preventing me from working on anything else at the same time.

The company folded shortly after its inception—we made the cardinal sin of leaving it too late to raise another round after the initial investment—which led me back to full time employment at Wise.

With the potential to work on new projects, curiosity led me back to Timo. And the discovery that for my year's absence Timo had users and gave us feedback on the product. After some deliberation we set to work. To rebuild Timo, and take it from a weekend project to a sustainable business. At the same time, I started at Wise and quickly moved into a leadership position.

Within three months of starting the leadership position, the pandemic struck and we went fully remote. Wise is a company who thrive from face-to-face communication. A particular brand of chaos ill-suited to working from home. Combined with my new role, my day-to-day life was intense.

With Byozo, I tasted the freedom of working for myself. Despite my work for Wise being intense in its own right, I persisted with developing the shiny new version of Timo. My day-to-evening was really intense.

I can't pretend that the two years of working at Wise and on Timo simultaneously were healthy or ideal. Some weeks would be productive, others filled with anxiety and depression. Balancing full time work, in a new position, with a project that you hang your future on is incredibly intense.

Yet, that time was some of the most rewarding time I spent. It's the time I built the most critical habit for any endeavour. Showing up. In a period of chaos in the world I showed up near every day for the last two years, for which I'm thankful for, as it has set me on a life path far better to which I had before.

I left Wise at the tail end of 2021. To reduce the intensity and give me freedom of thought once more. Quitting Wise loosened my belt. Shipping Timo allowed me to breathe.

Counting my privilege

To dramaticise, as of September 2021 I made myself unemployed and homeless. My partner and I both left our jobs and gave notice on our apartment. The plan, to move to Portugal, at least for the start of Winter, and test the waters by moving there more permanently.

The reality is far more privileged. I work a small amount of contract work which pays what bills I have. I have a roof over my head in the shape of Lydia's parents' house. In essence, I have hit the time jackpot without the cash flow to match. I can now spend my time on Timo or other projects as I see fit. The importance of building the habit of showing up is clear.

Vagabonding is a great inspiration for me. It laid the foundation of my thinking to even ask the question of whether this would be possible. To distil it's advice as succinctly as I can:

You do not need a lot of money to live a happy life and do as you wish. Money is required only for materialistic ideals.

A furnished apartment, a space that you can call your own. They're all valid desires to live a comfortable life. But right now I'm appreciating the scrappiness of my situation.

I want to recognise that this position won't continue forever. My aim is to move to Portugal as soon as possible (the visa process is underway) and create a sustainable position as we pursue our own businesses. Despite the anti-materialistic revelation, we will continue to pursue monetary success.

Monetary success being a critical piece of reaching true sustainability. True sustainability is the prerequisite for sharing wealth and the privilege that I have. The crescendo I envisage for myself.

I won't kid myself that this doesn't have the ring of a "how I made my first million" article, where the answer is inevitably borrowing money from their parents. I am instead borrowing time from my partner's parents. Which is quite some privilege.

And to emigrate to Portugal because we want to and because we can (visas pending) is another huge privilege.

A note I took while reading "A very short introduction to Socrates" seems apt here:

I cannot apologise for those of my skin, my nation, nor my privilege. Only can I learn from their behaviour and prevent wrongdoing by my hand. It is only my hand that I have any control over after all.


With my time-rich life, I'm attempting to plot the course for my future. On one hand, I have Timo. An early yet built product in a situation perfect for me. A learning curve in the art of marketing. In the other, a sense of opportunity to do what I enjoy: create.

I will take a leaf out of the Indie Hacker playbook now, notably Pieter Levels and Josh Pigford. I aim to be prolific. In writing, in shipping and in living.

In Elizabeth Filips' video "Productivity YouTube is brainwashing you", she makes the statement that a ladder against the wrong wall gets you to the wrong place faster. I disagree. A ladder placed is a ladder used, and climbing the ladder is the only way to find out if it's in the right place.

One critique of my approach has been overthinking. And I agree. I get satisfaction from deliberating over my ideas, sitting in Roam, collecting notes and building a picture of how I view the world. However, unless I share this with the world, then I am merely wasting time.

Then you have my inability to ship. I kicked off a number of smaller projects over the winter only to fail to ship any of them. Now that I've launched Timo, I have no valid excuse for doing so. Yet overthinking makes me question the validity of these small projects, posing the question of whether they're worth my time or mere procrastination.

Breaking the cycle

In an effort to change this and deliver on my idea of proliferation, I'm changing my approach. Despite having ideas for new projects stowed away ready to be started (though no domain names bought!), I'm looking to you for validation before I will.

My immediate aim is to talk with as many people as possible in the fields I have interest in. The key three being Product Analytics, Tools for Thought and design tooling.

If you're interested in following along, I'm summarising each conversation on Twitter:

When I say I'm looking to you, I mean it. If you're interested in these topics, or you know someone who is, I'd love to chat. Reach out to me on Twitter or via email

If you want to go more direct, feel free to book time in my calendar directly:

6 mins to read