Betting With Time

How to bet your time

I realised control over my time the day I graduated from University in Sheffield, UK, 2009. Or so I thought.

“I can’t work for a boss” was my only criterion when entering the world after education. Even at 22, I knew I couldn’t work a 9-5.

While my cogs turned on a solution and money was sparse, I interviewed for a job at the local college.

My heart wasn’t in it. The interview process irked me, the paperwork bored me and the thoughts of what my day-to-day might look like filled me with dread.

Luckily, I didn’t get the job. And the next week, I landed my first freelance web development client.

It might have looked like I had a lot of freedom—to my friends at least—back then. But it was years later that I’d come to understand true autonomy.

In truth, when you have things you want, bills you must pay and little savings, you’re only a smidgen freer in self-employment.

In the beginning, you’re grateful for whatever work you can get from whoever you can get it from. You can’t really choose how to bet your time; you just have the illusion of being able to.

When you need the work, you need to bend. It’s only as time goes by and opportunities increase that you arrive at the holy grail somewhat disappointed.

Four years into my freelancing career, I could start to be truly choosy. Clients, projects, what days I worked, how long I worked for. I had enough demand for my services and money in the bank to start making the mirage of freedom a reality.

If false autonomy is the first stage of trickery for those of us who go it alone to evade, inaction induced autonomy is the second stage.

When you need to work less to pay your way, you have more time to bet with. And when you’re new to this surplus, you often wager it unwisely.

Parkinson’s law states that “The amount of time that one has to perform a task is the amount of time it will take to complete the task.”

When you have plenty of ideas and ample time to work—as many entrepreneurs do—it’s effortless to fill your calendar with fake progress.

Eleven years since entering self-employment, the overriding question of 2021 isn’t which clients I work with or what days I work, but whether I work at all.

And having time to bet with is stifling if you let it.

A Polymaths’ Curse

When you’re interested in a range of domains, you pursue them all naturally. Often until the one you’re most interested in creeps ahead, the rest of the pack fall away and a career is born.

This is how my early years in business played out.

My interests centred around video game development, art and the internet. Then I concentrated on the development of WordPress websites and this is where my knowledge lay while I cut my teeth in the world.

But with each year came a new interest, or two, or three:

In my early-20s, I started reading business books to get my WordPress consultancy ahead.

My mid-20s saw me pursue fitness, routine and self-improvement.

My late-20s saw me start an eCommerce business, leading me to study copywriting, digital marketing and sales psychology.

My early-30s brought me into authorship, digital product creation and stock market investing.

The older I get, the wider my mind opens.

By trade, I’m a programmer who learns new things easily. It’s a blessing in business but a curse when knowing how to bet with your time once you hit the aforementioned surplus.

I’ve learned that shiny object syndrome is real and not overwhelming yourself is a business skill. Choosing from the menu of options your brain serves daily is tough.

A few items on my brain’s à la carte at present:

  • Could I take a year off?
  • Could I write more books?
  • Could I create a video course?
  • Could I build a SaaS product?
  • Could I start an agency or two?
  • Could I teach people how to code?
  • Could I coach freelancers more intensively?
  • Could I trade the stock market more actively?

These are solid suggestions because the answer to all of these questions is “yes”.

When your days aren’t decided for you—or a portion of them, at least—choosing three square meals instead of snacking is tricky. Because they’re all attractive and viable options.

This introduces the concept of Betting With Time.

How people with specific knowledge in multiple fields and a diverse set of skills choose to prioritise their time fascinates me.

How does one wager their most valuable asset effectively?

Your Most Valuable Asset

Your most valuable asset is time.

Here’s one of my favourite quotes on the relationship between time and money from entrepreneur and investor, Naval Ravikant:

Earn with your mind, not with your time.  Naval Ravikant

As someone who, in early life felt that my time would never run out and in early business, sold it hourly as a freelancer; clarity on this concept took—well, what would you know—time.

It’s difficult to understand the compounding effects of doing something well for a long time when you haven’t done something well for a long time.

Then you reach the tipping point and crystallisation of this concept is achieved:

You have to spend time early to make more later.

The Highest Form Of Wealth

The highest form of wealth is the ability to wake up every morning and say “I can do whatever I want today”.  Morgan Housel

When I read this excerpt from The Psychology of Money, I felt grateful. Business has been good to me and the autonomy I’ve engineered allows me a fulfilling life.

I’ve often thought about how my life would be different if I made a multi-million-pound exit from a company I own.

After the Lamborghini and a month in Las Vegas, it wouldn’t be much different at all:

Providing for my family and being of service to the world by solving interesting problems and doing things I find fun.

No matter how wealthy I get from this point—so long as I keep ticking over—the end-game day-to-day is pretty similar.

I’m wealthy already. Because I have control of my time.

But control brings with it conundrums:

  • How can I best provide for my family?
  • How can I best be of service to the world?
  • How can I be the most fulfilled?
  • How can I have the most fun?

What do I bet my time on?

Deciding What To Bet On

I’m not risk-averse.

I’m partial to a sports bet, like to run my own investment portfolio and I pulled our new house to bits with a baby on the way.

As an overall assured person, making decisions never came difficult to me. Because—even if I didn’t realise it at the time—many of these decisions were already made.

The client was taken because my mobile phone bill needed paying and I worked evenings because I wanted a holiday.

As I write this, I don’t need to do anything to fulfil either.

With greater control of your time, decisions become harder until you prioritise with care:

“I could work on X, Y or Z; but what should I would on?”

I’ve realised that I won’t be able to do it all and I’m becoming OK with that; not every idea is a good idea.

So this presents the question:

How does one navigate betting with their time?

Here are my non-negotiables:


My family will always come first. I refuse to play a non-active role as a father, husband, son, brother and uncle in favour of busyness for busyness’ sake.

The first portion of my betting budget is allocated here.


My health relies on exercise.

Working out gives me clarity and allows me to take care of myself so that I can be better for those I care about.

I’ll always bet on exercise.


I’ve always freelanced in a life-first fashion.

There’s no point in working to level-up your life—beyond a certain point—if you never take time to enjoy the life that you’re levelling-up.

I get a lot from the perspective offered by friends and travel in particular.

Things that are I enjoy will receive an allocation.


Omitting family, health and life from your time priorities harms work time.

When work time is in oversupply and you love what you do, you’re susceptible to a blinkered vision of what success takes.

A perspective of, “I’ll get more done if I don’t take a walk/work out/go to the football game” is counter-intuitive, because each priority supports the others.

Sure, you might get more done in the short-term. But is it sustainable? And how’s the quality of the work you did on no sleep? How present were you eating dinner with your family?

That lesson has already been learned.

With essential time allotted, what’s non-negotiable when betting on business pursuits?

Here’s my working ruleset:

  1. Take risks while retaining wealth (autonomy)
  2. Realise that you can’t (and don’t have to) do it all alone
  3. Increase the surface area of success without overburdening yourself
  4. Make it fun and consistency will come as a byproduct
  5. Identify long-term opportunities with compounding benefits
  6. Invest in connections with effective people

While I’m prepared to gamble, I like the odds to make sense; whether that be on my football accumulators, the companies I invest in or when betting with my time.

And I believe these rules bring clarity when deciding what to bet on.

Hedging Your Bets

I write ten, sometimes twenty notes per day. Inspiration can strike at any time. Often while working on something unrelated, usually while walking my dog and sometimes in the middle of the night.

Remembering things is hard for me. I can’t remember a three-point shopping list without cementing it in my Notes app.

Equally, when a business idea arrives, I have to get it out of my head if I want to remember it.

The upside of having many ideas is that you have them, the downside is that you’ll never have time to action them all. You need to bring an idea to market to see if it’s a good idea.

While we’ve covered how to help you decide what to bet your time on, we’ve yet to approach volume:

How many ideas should one give focus to at any one time?

“Niching down” is a smart play and I owe a lot of my success in freelancing to the practice of this concept. However, a generalist can still be a specialist in their marketing.

For instance, I can still be a WordPress consultant to the people who land on my website through a Google search. And I can still help people get ahead in their freelancing careers through sharing my experience on Twitter.

You can be different things to different people and you don’t have to hang your hat on one quest forever. That wouldn’t be a smart play. You’ve got to move with the world because it’s not stopping for you.

One could argue that the multi-faceted approach is a personal brand enhancer as opposed to a personal brand diluter. Of course, talking about dolphins and gardening when starting to build a brand wouldn’t make sense.

Paradoxically, after focusing on one thing for a while, synergising dolphins and gardening may become your ticket to freedom. Or as writing expert David Perell coined it, your “Personal Monopoly”.

A unique intersection of skills, interests and personality traits that make you one-of-a-kind.  David Perell

It’s impossible to commit an appropriate amount of time to ten or twenty ideas at once. Most would agree on that. Yet one source of effort feels equal parts boring and risky.

Which leaves you to ponder:

What’s the magic number of concurrent viable pursuits?

Self-employment champion Daniel Vassallo describes his business as “A Portfolio Of Small Bets”. At the time of writing, his Twitter bio shows four active paths.

Having worked on a project basis for the past decade, I’m left with similar conclusions:

  • 1 project is pedestrian
  • 2 projects are steady
  • 3 projects are great
  • 4 projects are challenging yet manageable

My portfolio of pursuits has begun naturally arranging itself into position:

  1. Growth of my WordPress consulting business
  2. Helping freelancers through content, mentorship and digital products
  3. A SaaS product (TBA)
  4. Open, for now

The key to each pursuit being that I remain autonomous, with the ability to add more or less input as required. Just like when your kids need different things at different times; you still love them the same under varying attention.

I believe the solution to Betting With Time is to take risks under due diligence.

Think, “Which opportunities have both the biggest upside and the least chance of failing?“.

Think, “How much can I realistically handle—alone or with a small team—without experiencing diminishing returns in the rest of my life?“.

Think, “Can I fail and stay alive financially?“.

To bet with time effectively, you must increase your surface area of success without overwhelming yourself.

Betting With Time means to carefully consider what fulfils you and what makes the most sense to pursue.

Because life is a gamble and time is the currency.