The Simple Yet Radical System to Change Your Life

Your to-do list is failing you. Read more to find out how and why.

John Gruber
Aug 3 · 10 min read

The world of tech startups is unlike anything the world has seen before. They need to be fast, cutting-edge, and pivot on a dime. Not only that, they need to scale faster than anyone thought possible. But how?

How do they lead a small startup of 2 people one day and a mega-corporation the next? And what’s this have to do with a to-do list?

We tend to think companies like Google and Twitter have amazing world-changing ideas. But Google wasn’t the first search engine and Twitter wasn’t the first social media platform. Google was the 18th search engine to the market. In the IT world, that’s almost always a bad bet.

Being 18th means the market is saturated. Larger companies have taken too much market share for the little dog to enter the ring. So how did they succeed in changing the world and what does that mean for us? Let’s jump back in time and find out.

On a cool autumn day in 1999, Lary Page and Sergey Brin were making one of the most important pitches of their lives. A day that changed the course of computing and the world. Larry and Sergey were looking for capital to help launch their new company, Google. They wanted to make the internet exponentially more relevant. They had a big vision of how the world would work in the future. But there was a problem…

John Doerr bought into their vision and made the biggest investment of his career investing $12.5 million for a stake in Google. He knew they were going to make it. But he also saw a problem, Larry and Sergey didn’t have a management style that could grow as fast as Google.

What Google needed was a system to push themselves beyond their limits. A system that helped keep everyone on track. They needed innovation. The type of innovation that only happens when people are free to visualize and execute in their own way. What they needed was Objectives and Key Results (OKR).

OKRs became the simple tool that institutionalized the founders’ ‘think big’ ethos. — How Google Works

Want to know the best part? OKRs are used at large corporations, small teams, and even on an individual level to accomplish more than you ever thought possible. By changing the way you create a to-do list you can set higher goals and create a clear vision on how you achieve them. It’s easier than you think.

What're Objectives and key results (OKR)?

source: PeopleMatters

The system is simple, you have objectives and key results. That’s it.

The objective is what you want to achieve. “Be a full-time freelance writer.” That’s an objective.

Key results are assigned to an objective. They’re time-bound and measurable. “Write one evergreen article a week with 10,000 readers within 2 weeks.” That’s a key result.

Objectives are big and lofty goals. It’s the dream you want to accomplish. Key Results give us specific, measurable results to strive for. They answer “how do you know you’ve achieved your objectives?”

Key results become major milestones that need to be conquered. Key results aren’t a to-do list. They’re ways to measure the success of your objective.

So what does an OKR look like for this article?

Objective: Write an article to help people achieve more in life.
Key Result 1: Write and publish the article within 3 days.
Key Result 2: Have 1,000 reads in the first 2 weeks.

It seems simple but it’s so powerful it’s used by every employee at Google from the CEO down. It’s used at organizations like Intel, Twitter, the Gates Foundation, and many more. You’re probably wondering the same thing I was when I first started using OKRs. Does this system really work on a personal level too?

If you read the title of this article the answer won’t surprise you. Yes! OKR fixes three major flaws in the standard to-do list. Flaws that are keeping you from achieving greatness.

1. The Never-Ending To-Do List

The archaic to-do list has a problem and its a big one. It becomes crowded with day-to-day tasks. From taking out the trash to picking up the kids. We live in a busy world. A world that never sleeps. The constant chatter drowns out big goals. Goals become fantasies. Fantasies that we begin to realize will never come true.

I know what your thinking. “But that stuff needs to get done.” Does it though? What would happen if you only did the dishes every other day? What if you planned a babysitter for one night a week so you can focus on you? What if you only showered once a month? Okay, maybe some of the daily grind needs to stay, but does all of it?

You should matter in your life. Your goals should matter. What you want to accomplish in your life is important.

If you need a reminder for day to day tasks run two lists. My standard to-do list includes taking care of the lawn and paying the bills and then I have my OKRs. My OKRs become the items that I MUST accomplish to achieve my dreams. But how does OKR help us make our dreams the priority in our life?

The Time-Bound Cycle

The OKR system works in a simple cycle typically every quarter or month. Define one to five objectives for yourself. These are the most important goals of the next quarter.

These objectives aren’t run of the mill to-do items. That’s not for us! These are big-ticket items. Objectives are big, life-changing items. They must drive us to a major goal. When you achieve an objective it should be clear that you are closer to living the life you want.

You should never complete an objective and wonder if it really helped you in the long run.

By writing down your most important objectives you make them concrete. You take ownership of them. Hang them on your wall. Block out time on your calendar. Do whatever it takes to keep them top of mind. Let the small stuff fall through the cracks for once and make the most important things top of mind.

What If My Objectives Take Longer than A year?

This is where things really start to take shape. OKR is scalable. Google runs two OKR cycles one yearly and one quarterly. Do the same.

Want to travel the world but know it could take a year or more to make enough passive income to quit your job? Create a few yearly OKRs then break down the work-load by quarterly cycles.

Here’s what your OKRs may look like:

Yearly Objective: Quit my job and live off my passive income
Key result: Have $60,000/year salary from passive income
Key result: Run a successful online training session helping others start a business

1st Quarter Objective: Create a website and training session.
Key result: Launch website and training session.
Key Result: Give the program away to 10 people for honest feedback.

2nd Quarter Objective: Grow the training session.
Key result: Have 10 paying customers.

3rd Quarter Objective: Grow the training session.
Key result: Have 50 new paying customers per month.

4th Quarter Objective: Turn business into a passive income.
Key result: Hire a team to perform the job.
Key result: Create social media and ad calendar.

That’s all it takes to get started changing your life. Taking a life-changing leap isn’t easy. But the never-ending to-do list is the only roadblock. There’s been something else keeping you from accomplishing everything you want.

Fear. Fear that you’ll fail. Fear that you’re not good enough. Fear that you can’t do it. Don’t worry. There’s a solution.

2. What If I Fail?

The year was 2008, Sundar Pichai was Google’s VP of product development. Responsible for Google’s not yet released browser, Chrome. They had 0 people using the browser. Sundar was ambitious and optimistic. He wanted 20 million users by the end of the year. Even for Google, it was crazy growth.

So Sundar created an OKR and his team set off. The browser was released to Windows but the Mac version was late. Sundar’s team couldn’t hit there 20 million users objective. This might have been a problem for others, but Sundar and his team had an OKR mindset. Sundar had one message to communicate.

No, we didn’t reach the goal, but we are laying the foundation to break through this barrier. Now, what are we going to do differently?

In 2009 they set another OKR, 50 million users. They ended the year at 37 million. Another failure.

The following year they set a new goal of 111 million users. Despite previous failures, they continued to believe. They continued to set higher and higher goals. In the fourth quarter of 2010, they did it. They hit their mark of 111 million users.

Today, Sundar is the CEO of Google. His failures didn’t stop him from succeeding. They didn’t slow him down. They didn’t stop him.

So what if you fail to complete an objective? What’s the worse that can happen?

Objectives should be challenging yet realistic. They should push you further than you thought possible. If you’re writing currently gets 10,000 reads a month set the goal for 10,000 reads a week.

Make your objectives challenging and don’t be afraid to fail. Give yourself a time-bound challenge. Challenging but be realistic about what you can accomplish in the allotted time. And never be afraid to fail.

There’s one last problem with the to-do list…

3. Motivation

The last piece of the puzzle. The last giant hurdle that everyone stumbles on. Call it what you will. Motivation, burn out, washed-out, lack of drive. It’s such a big problem we’ve given it a hundred names all of which mean the same thing. We stop believing the work that needs to be expended isn’t worth the reward.

We all have difficulties getting out of bed or working on personal goals after a long day of work. The universe beats us down until we don’t have the strength to get up.

How to stay motivated isn’t something that comes naturally. We’re not taught it in schools. We don’t find extra in our pocket. You can’t just jump on Amazon and buy it. It’s hidden in us. You need a better goal-setting system to put coals on the fire and keep the engine moving. But how does motivation work and why do some systems work better than others?

Elle Kaplan has a great write-up on motivation where she explains how goals and motivation fit together. Honestly, I didn’t know how motivation worked until I read her article. I started using OKR and the motivation just showed up. I was happy it was there but I didn’t ask any questions. I was terrified the sneaky little bugger might take off again.

So what’s it take to stay motivated especially over longer periods of time?

Set Specific Yet Challenging Goals

People who set goals that are both specific and challenging are 90% more likely to achieve what they’ve set their mind to. — American Psychological Association

There it is. An OKR in a nutshell. The objective is challenging. It drives us to be better than our best. It says “this is more than you’ve done before but you can do it”. The key results are specific. They have a timestamp and they give us a clear measurable way to reach our objectives.

Objectives and key results are the one-two punch combination for demotivation. The bee’s knees for motivation.

Unfortunately, motivation comes and goes. An OKR will motivate us but we need one more change to stay motivated.

Celebrate the wins (and the losses)

In OKR you’re constantly striving to push your own limits. When pushing your own limits you’re going to be challenged and you’re going to fail. Part of the OKR system is the mindset. Stop thinking of failures as a negative. Pushing yourself past your previous limits is a win. Let me put it another way

Let’s say you like to run and your best mile time is 10 minutes. One beautiful Saturday morning you decide to go for a run. But today, you decide you’re going to set your mile time at 8 minutes. You hit the trail, pushing harder than you ever have. When you cross the finish line you check your time in anticipation. You failed. You ran it in 9 minutes. While you didn’t reach your goal of 8 minutes it’s your best time yet. Do you celebrate or walk home with your tail between your legs? With an OKR mindset, you pop the champagne! That’s a huge win!

Want to know the best part of the OKR system? It’s free.

What tools do you need?

Nothing. You don’t need to spend a dime on a fancy app or a single minute on how to make the app work on your devices.

When Intel first implemented OKRs in the 1960s they didn’t have a fancy piece of cloud software. They didn’t have smartphones to track there successes and failures. They printed out OKR’s with ink and paper and transformed their business and their mindset.

There’s a lot of great OKR software for teams and organizations. I’m sure you could use them on a personal level too. Honestly, they’re not needed. Open up a word document, open up your journal, put them on a whiteboard. It doesn’t matter, they’re short and sweet.

How to get started changing your life

  1. Determine how long you’re OKR cycle will be. Will it be for one month, 3 months or more? Your first cycle may be short or long to help you map your cycles with the Gregorian calendar. Make it work and get started right away.
  2. Write down three to five objectives. What are the most important things you need to accomplish in the next few months to change your life?
  3. Right three to five key results per objective. How do you know if you’ve achieved your objective?
  4. Make you and your dreams a priority. Get to work accomplishing your key results.

References

The Crossover Blog

Welcome to the future of work. The Crossover blog is your resource for staying up to date on topics that matter in the modern workplace-like tech skills, remote work, recruiting insights, and more. Learn more about Crossover and browse remote tech jobs at www.crossover.com.

John Gruber

Written by

Productivity and technology to make the world a better place. Because we all need a little help and motivation sometimes.

The Crossover Blog

Welcome to the future of work. The Crossover blog is your resource for staying up to date on topics that matter in the modern workplace-like tech skills, remote work, recruiting insights, and more. Learn more about Crossover and browse remote tech jobs at www.crossover.com.

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