Lifestyle Design

I waited 28 years before questioning the end goal

I spent years working with an incomplete view of success. Scaling the corporate ladder and building the next $1 billion business was the game plan. Over time, I got closer to achieving my goals, and that was the problem.

The Epiphany

For years, I optimised my income without respect to my lifestyle. My work accommodated my life as opposed to the inverse:

I was juggling permanent work, startup life and 101 personal commitments. I was burning out, sacrificing too much - and it wasn’t worth it.

Ask The Right Questions

I knew I wasn’t satisfied with my current trajectory anymore, but I couldn’t put my finger on the source of my frustration. Reading books like The 4-Hour Workweek and Built To Sell helped me to ask better questions:

  • Do you need to work so intensely to meet your needs? Or are you working for work’s sake?

  • How much money would you need before you have “enough”? Or are you spending your life saving up an indefinite amount?

  • What did you sacrifice for a higher income? Time? Mobility? Sleep? Family? Happiness? Mental Health?… Was it worth it?

  • Will your trajectory lead you towards your target lifestyle? Or would it require more sacrifice, moving you further away?

  • Do you want your boss’s job?

  • What exactly would you want to do in retirement? Are you waiting because of compulsion or convention?

  • Is it necessary for everyone to work a 9-5 for 40-50 years and then retire?

What’s The Alternative?

Lifestyle Design.

The freedom available via a lifestyle first approach is more holistic than work-life balance. You define your priorities and schedule - then you figure out how how to monetise it with minimal effort.

  • For Tim Ferriss, disconnecting your income from your time and location is fundamental.

  • For others, it’s about assessing your real priorities in life and working in line with them.

I decided to change tomorrow’s course by reassessing my priorities now - instead of riding yesterday’s momentum in the wrong direction. The design differs by person, but it optimises the process alongside the results. (Share this on Twitter)


The Japanese have a helpful concept called Ikigai ("a reason for being").

It argues that the most purposeful actions are enjoyable, helpful, skilful, and something we can monetise. Ikigai enhances our framework for assessing what we pursue.

Answering Objections

Here are some objections that may make inaction attractive and the responses:

“I’m already too far down another path.”

This is sunk cost fallacy.

“If the recipe sucks, it doesn’t matter how good a cook you are… The consequences of bad decisions, do not get better with age." - Tim Ferriss

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“This sounds way too risky.”

Most people will choose unhappiness over uncertainty. However, we can mitigate most risks once we’ve clearly defined them.

Additionally, they are usually less scary once you take them.

If we define risk as “the likelihood of an irreversible negative outcome,” inaction is the greatest risk of all. - Tim Ferriss

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"Action may not always bring happiness, but there is no happiness without action." Benjamin Disraeli, former British Prime Minister

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“If it were this easy, everyone would do it.”

The real problem isn’t the difficulty executing. The challenge is rejecting conventional wisdom and being different.

“Humans are herd animals. We want to fit in, to bond with others, and to earn the respect and approval of our peers.” - James Clear

Even social media incentives the perception of success and happiness more than the reality itself. Fitting in is more important to us than we often care to admit.

“This is only good for those who can code.”

Not at all - this can work for anyone. If you need to build a product, validate the idea for free, then outsource the build or use solutions that don’t require any code (I will write on this soon).

Alternatively, I’ve seen plenty of successful information products (e.g. newsletters and ebooks) making in 6-7 figures in annual revenue.

Food For Thought

Article by Julain Shapiro - What to work on

Exercise: Finding your Ikigai

Video: Mastering the Lifestyle-First Approach to Indie Hacking with Daniel Vassallo and Courtland Allen

Podcast by Courtland Allen and Dru Riley: Persisting Through Failures to Find a Winning Trend

A Challenge:

I’ll aim to do Jack’s challenge over the next two weeks with a new product and get back to you with the progress. If you’re interested, join me - and let me know how you get on! You can also follow along my journey on Twitter!

Twitter | LinkedIn | Indie Hackers | Product Hunt | Personal Site

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