five years

What Would You Do With Five Years?

Image courtesy of Superbomba

“For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.” – Steve Jobs, in Commencement Address to Stanford students

What would you do if you were told you had five years left to live? I prefer to use this rather than Steve Job’s single day, because most of us, with a day or week left, would spend them seeing family and saying goodbyes.

But five years is different. Five years is long enough to accomplish almost any goal you might have, however ambitious. And you wouldn’t want to spend five years partying hedonistically, or eating your favourite meal every night.

Would you finally get around to writing that novel that you’ve been planning for more years than you want to admit? Would you quit your job and set up your own business – secure in the knowledge that your retirement fund is no longer a problem? Would you find the means and the money to travel to places you’ve always wanted to visit?

Don’t Put Your Life On Hold

I live in London, where people my age (twenty-four) often say something like this:

    If I work 50 or 60 hour weeks for the next twenty years, I’ll eventually reach the top … then I’ll be able to retire early and do exactly what I want.

But why wait most of your life to be allowed to enjoy yourself – especially when you’re likely to have worked yourself to a breakdown or burnout long before then?

If you’re living for the future, working in a job you hate because you think it’ll benefit you in 30 or 40 years, think about your answer to what you’d do if you only had five years left. What’s stopping you going for it now? Are you really stuck – or just lacking the courage to move on?

Don’t Follow the Herd

When I graduated from university, I took the path that I thought was “expected” of people my age. I found a job as quickly as possible, moved to London, began renting from a landlord for the first time (I’d lived with my parents and then in college halls). After a month I was asking myself “Is this it?”

I stuck with that job – a dead-end from my point of view, as it was in a company and career I had no interest in staying with long-term – for almost two years. Then I managed to take the plunge into doing what I love for a living: writing and helping out small business owners with their websites. The hardest thing about doing this was going against the flow – explaining to people whose attitude was “Of course work sucks, that’s life” that it didn’t have to be that way.

Make Every Year Count

The good news is, I hope, that you don’t only have five years left. You might have twenty, forty or sixty years ahead of you. Make each of them count.

Some resources that I’ve found very useful in this are:


Dan Miller’s No More Mondays (If you’re unhappy in your current job, read this. Even if you’re self-employed like me, there’s loads of good advice in here.)

Dan Clements and Tara Gignac’s Escape 101 (Think you might not be following the right path, but unsure what you do want to do? Why not take a career break – a sabbatical – and find out what other opportunities are out there.)

Tim Ferris’ Four Hour Work Week (I know you’ll have seen this recommended on half the blogs on the web, but it really is a great, mind-opening read.)

Tim Brownson’s Don’t Ask Stupid Questions – There Are No Stupid Questions (This isn’t just fantastic advice for career and purpose – it’ll help with all aspects of your life.)


Anywired (great blog archives for anyone aspiring to a “work from anywhere” lifestyle)

FreelanceSwitch (if you’re thinking of taking the plunge and quitting your job to freelance)

Men with Pens (great business advice, ideal for writers or designers but applicable to many freelancers)

IttyBiz (tips, especially on marketing, for small businesses)

The Discomfort Zone (a great way to start thinking differently and pushing yourself out of your comfort zone – pretty essential if you’re going to break away from the herd)

So what would you do with your five years? What’s that big project you’ve been dreaming about for years, or that idea you’ve only half formed? Let us know in the comments.

About the author: Ali is a postgraduate student and professional writer. She runs Alpha Student (grab the RSS feed), a blog which aims to help students get the most of their time at university.

Got a Self Improvement Question? Click Here!


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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