The Power of Working Backwards

Josh Sowin
Between Letters
Published in
6 min readJun 5, 2016

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A simple trick to help you accomplish hard things

Have you ever wanted to do something big, but then got too discouraged because it’s… well… too big?

Here’s the truth: important things are hard to accomplish. Possible, but hard. And the difference between those who accomplish hard things and those who don’t is the application of a very simple technique.

I call it “working backwards” and it’s one of the most powerful ways to change your future and fortune.

Many of us are locked in the present. Not a mindful present, but a constant stream of distractions. Our minds flutter from one shiny thing to another. We wake up and check Facebook. We Snapchat. We text. WeChat. Check Facebook again. Email. Facebook. Instagram. Some game we’re totally not addicted to. Choosing where to eat. Listen to music. We feel a slight prick of boredom so we pick up our phone and ooooooo we have notifications! Dopamine! 27 kittens inspired by kittens watching kittens. Drinks. TV. Sleep. Rinse, repeat.

We are busy. Oh so busy. As are the ants, pointed out Thoreau.

But what are we busy about?

I struggle with this question at the end of most days. Benjamin Franklin would ask himself, “What good have I done today?” as each day closed. When I ask myself that, I feel insufficient — I could have done more. I could have focused on more important things. I could have pushed myself harder. I could have helped others more. Sometimes this turns into self-loathing which is unhealthy and yet even now I can’t bring myself to say is inaccurate. For I know that I am capable of more.

But more what? What are we trying to ultimately accomplish? It’s like being disappointed with yourself for not rowing a boat more — sometimes you need to take a step back and make sure you’re even going in the right direction. What if you’re going in the wrong one? Rowing more would just make things worse.

Working Backwards gives you direction and guidance to achieve your direction:

1. Imagine your desired future outcome.
2. Break it into achievable actions.
3. Work daily towards accomplishing it.

It’s so simple, right? And yet this is how anyone can accomplish hard things.

Let’s say someone wants to live a life that positively impacts those around us. A worthy goal. But it’s also something that won’t happen without effort and planning.

Here’s where Working Backwards comes in.

Imagine your funeral.

I’m not sure how you’re there — that’s not important, stay with me here. You pass through the church wall. You do this because you’re a ghost, and you pass through walls just for the hell of it. You sit in a pew, or at least pretend to, and wait. Who will come? What will they say? What will the eulogy be? What will people say about you as they drink wine and munch on cheese? Will they ask each other what the wifi password is?

Let’s say you want a ton of people to show up, to have them talking positively about you, and giving examples on how you’ve helped them. This would be evidence you really did make an impact — and it’s totally possible for anyone to achieve. But if you want that outcome, you have to work towards it. You have to actually start helping people, and not just once or twice, but consistently over a lifetime. You have to get out there and meet new people, listen to them, and work actively to solve their problems and make their lives better.

After a couple years of doing this you will have significantly changed the outcome of your funeral. That’s the power of Working Backwards — big changes are within your grasp. And it’s applicable to anything.

Want to write a book?

Start with the title and cover. Get it designed for cheap on 99designs and put it by your computer. Write some imagined reviews — what would you want others to say about it? Now outline it and start writing a little each day. 500 words a day can easily be written in 30–60 minutes a day. Don’t stop to edit. In a couple months you have your first draft written!

Want to retire a millionaire?

That became a goal of mine when I turned 25, so I worked backwards: I created a spreadsheet where my net worth ended with $1,000,000 at 50. The result was immensely achievable: all I had to do was figure out how to save $900 a month, which works out to $30 a day. If I invested that monthly in no-load index funds, I’d be a millionaire by 50 and be able to live off the interest for the rest of my life (assuming I lived frugally). So I cut back on luxuries like eating out and expensive coffee and passed on shiny things. But you know what? I’ll retire a millionaire.

Want to create a business?

Picture what it looks like in its prime — that’s your audacious goal. Now break it down into yearly and monthly projections. Then get to work, thou sluggard, and track your income and expenses every day.

Want to rob a bank?

No, don’t do that. Seriously what’s wrong with you.

George was just working backwards to change his nickname.

Want to learn how to code?

When I wanted to learn PHP I came up with a simple business idea. I designed what it would look like when I finished. Then I got a bunch of books, downloaded sample scripts, and then started code little by little each evening after work. A couple months later I had a business I coded myself that was generating income. Later I sold it.

Want to run a marathon?

Well, that sounds a bit nuts to me, but okay. Work backwards — the goal is to run 26 miles. Start out with one mile. Then two. Then three. And keep on going until you can run 26 miles, tracking your progress as you go.

Want to have a baby?

Well, okay, this one’s pretty easy to do even by accident.

Want to be a musician?

Let’s say you want to learn guitar. Imagine what it’s like to be your ideal guitarist. What knowledge lets them play that well? How much did they practice? Make a list of all the skills they know and start from the basics. Practice every day just like they did. Within a few years you’ll have achieved mastery.

All of this is about visualizing a final destination, then making a plan to get there. Then you do something each day to get there. With every step you get a closer to your destination.

This makes accomplishing big, hard things possible.

Daily tracking makes a huge difference as well. I always have a calendar or app or spreadsheet that tracks my daily/weekly/monthly progress on an important goal. And turning it into friendly competition (or friendly accountability) can also make a huge difference. There’s a reason most successful people have mentors and coaches and personal trainers.

Learn from those who don’t do this. Some make no effort to get to important life destinations. They die without accomplishing their potential. Others are like matches that burn brightly but then disappear — they dive too intensely into things and then quit because it’s too hard or they’re too tired.

Remember: Small steps, done consistently, towards a predetermined direction. This will allow you to arrive at your destination. That’s the power of working backwards.

Now please excuse me while I cross off today’s writing goal and reward myself with some strawberry ice cream.

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