“Where do you see yourself in five years?”
As a young professional, I used to cringe every time I hear this question. It’s so cliché, and way too personal. I’d end up answering with something vague like “Doing something I love at an organization I believe in!” Ugh.
I’d imagined where I wanted to be in five years – but I’d never written anything down. I felt super self-conscious putting my random thoughts and ambitions on paper. I was barely keeping my head above water on a day-to-day basis. The prospect of thinking and planning more than a few weeks ahead was absolutely exhausting.
“Where do you see yourself in five years?”
For most of us, if we’re being honest with ourselves, the answer is “I have no idea.” Raise your hand if you’ve been there.
A few years ago, I wrote a bucket list. Some highlights:
- Exercise more (??? So vague. What does this even mean?)
- Go to a roller derby (I think I had just seen Whip It?)
- Learn Spanish
- Adopt a dog and cat who become best friends and then become Instagram famous (Still valid and now in my 5-year plan)
- Live in a different country
They were all over the map. Plus, there was no way I’d be able to cross all of them off. There aren’t enough hours in the day. This was when I started feeling some serious anxiety.
Not only did I have way too many goals, but most of them were too fuzzy and undefined. I needed to trim the fat and prioritize.
I started reading a ton self-help books and followed every productivity expert I could find on Twitter. I went through the entire catalog of Lifehacker. So many life hacks and 10-second tips.
Through trial and error, I cobbled together the best parts of several different productivity philosophies into a system that’s helped organized my thoughts and my goals and kept me from being overwhelmed in my day-to-day life.
Today, this methodology helps me stay on track with both my short- and long-term goals. With it, I’ve been able to achieve consistent progress towards my personal and professional objectives. Now, I’m going to break down this method for you so that you can implement it for yourself.
If you follow along, you’ll start waking up every day with a sense of purpose, crushing your goals, and spending your time the way you want to. Sound good?
Fair warning – this guide is on the long side, clocking in at 2,500+ words. However, if you take the time now, it’s going to save you a crazy amount of blood, sweat, and tears going forward – reaping dividends for years to come.
Do yourself a favor and read through to the end, completing the recommended action steps as you go. In return, I’ll share all the downloadable resources and tools you need to get started.
“Where do you see yourself in 5 years?”
The next time someone asks you this terrible question, you’ll be able to answer with confidence. Sound good? Let’s get rolling.
Your tools for success – the simpler the better
Before I talk about how to set your goals, you need a place to put them.
There are truckloads of goal setting apps out there. A lot of them are based around the idea of streaks and habit tracking. I’ve tried many of these, and the functionality they offer isn’t worth the trouble of having a separate app. The novelty of these apps fades quickly, and checking them every day eventually becomes a chore.
The minimalist in me likes to depend on one single tool for my to-do list and goal-setting, capturing everything into it. This reduces my mental fatigue and keeps things simple.
ACTION STEPS (5 minutes):
- Download one of the following free apps on your phone. Cross platform compatibility is a must so you can access it on the go and at your computer.
- On your desktop computer and/or laptop, make the web version of your app the homepage on your browser (Chrome, Firefox, Safari, Internet Explorer).
- Create an account for your app of choice so it syncs across web and mobile.
Creating a gameplan for your goals
Now that you have the tools to track and capture your goals, let’s talk about how to actually create them.
One of the most powerful goal-setting systems around was inspired by Intel and popularized by Google. It’s called Objectives and Key Results, or OKRs for short.
OKRs are a productivity and accountability tool that emphasize transparency and continued self-reflection. Companies and teams use it to great success. OKRs allow you to easily track your progress and break down your goals into actionable steps. Crucially, OKRs are lightweight, simple, and easy to set up, and generate incredible momentum once you get started.
We’re going to flip OKRs around and apply them – with a few key modifications – to your personal goals, where they can have the same powerful effect.
Objectives can be anything from a physical feat to a professional goal. They may or may not be measurable, but Objectives should align with activities you enjoy or milestones you want to accomplish. You should have a maximum of 5 Objectives going at a time.
- Examples could be: “Run a marathon.” “Get a new job.” “Learn enough Spanish to hold a conversation with a native speaker.”
- Think of these as your New Year’s Resolutions, except you’re going to start right now rather than waiting until January of next year. They should be ambitious and feel just a little uncomfortable.
- When setting a new objective, be specific and use language that conveys an endpoint for your objective so you know when you’ve achieved it. Try to avoid expressions that keep the status quo, like “Continue x” or “Maintain y”.
Key Results are short-term goals that roll up into an Objective. If completed, these measurable milestones should move you towards their corresponding Objective. When you’re setting these, your Key Results should describe outcomes rather than activities. You get up to 4 of these per Objective.
- Key Results should always contain a number so that you can quantify your progress.
- For example, with an Objective of “Get a new job”, some Key Results could be “Find five new companies I want to work for”, “Email 15 contacts in my network about job search”, or “Send out 10 job applications.”
Here are some tips on how to set your first Objective.
From Pick Your Goals:
What things do you value in life? Are they tangible things like a job, a career, education, a home? Or is what you value less tangible – relationships, humanity, animal treatment, world hunger, etc.?
What would you like to see changed about the things you value?
Do you have any experience or qualities that can help make change happen?
What are those qualities?
What do you still need to learn to make changes possible?
What kind of support system do you have?
Where can I go if I have questions or need information?
Jason Evanish chimes in:
If money wasn’t an object, what would you do every day?
What are your super powers? What powers would you want to develop?
As a kid, what did you want to be when you grew up?
Who do you really admire? Why?
ACTION STEPS (10 minutes):
- Brainstorm 1 Objective and capture it in Todoist as a Project. (Don’t spend too much time thinking about it, just get something down on paper for now.)
- Draft 3 to 4 Key Results for this Objective and capture them in Todoist as Sub-Projects under the Objective. It should look something like this:
How to consistently execute and achieve massive results
If you’ve been following along, you’ve already captured at least one Objective and its Key Results in your universe app. Before you get started building out your to-do lists, a quick story:
You might remember hearing about this Washington Post article by Darlena Cuhna, where Darlena shared her experience of driving her husband’s Mercedes to pick up food stamps after her husband lost his job and her twins were born six weeks early. It was a fascinating story about how quickly poverty can hit any one of us, no matter how secure we might feel in the moment.
Darlena’s article went viral and ended up becoming the Post’s most read story of all time, and producers and publishers started pursuing her for TV and book deals. With one single article, Darlena catapulted her career to another level.
You might think this article going viral and getting the exposure it did was based on a stroke of luck. The truth is, more often than not, getting your “big break” is actually the result of years of consistent hard work in the face of constant rejection. In fact, Darlena wrote thousands of articles before this one hit it big.
You probably hear it over and over again, but there really is no such thing as overnight success. It’s about showing up, day after day, and putting in the work.
When you circle back to the realm of self-improvement, the same thing applies. Achieving your goals isn’t going to happen easily. Over the short term, it’s definitely going to come with setbacks and disappointments. The key is consistency.
Unfortunately, it’s not that easy. When it comes to getting things done, we’re our own worst enemy. We tend to come up with every excuse under the sun to justify our behavior, even if it’s self-destructive and counterproductive.
When you’re looking to make a real lifestyle change, you need to be very intentional if you want it to really stick. To do so, Stanford psychologist and researcher B.J. Fogg recommends establishing a behavior change that is so easy and automatic that it slips right into your existing daily routine.
Fogg calls these tiny habits. By combining them with the self-review mechanism of OKRs, you’ll create a beautiful feedback loop where you start to execute consistently, see results, and gradually build confidence in yourself.
Identifying tiny habits is the #1 most important first step to take before building out the rest of your task list for each of your Key Results. By training your brain to succeed with small adjustments, you’ll stay motivated over the long-term on the path to achieving your goals. Plus, as one of my favorite writers James Clear says, even an improvement of 1% every day can compound and add up surprisingly fast.
Here’s how to create a tiny habit using B.J. Fogg’s method:
- Get specific about your goal. You’ve already done this by thinking of a few Key Results.
- Make it easy. Identify a painless behavior change that will put you on the path towards achieving that KR. This might take some introspection.
- Trigger the behavior. Find an existing trigger or create one that prompts the behavior, and link your new habit with it.
As an example, you could break down the Key Result “Find five new companies I want to work for” into a recurring tiny habit that’s tacked onto an existing habit: “When I get home from my commute and open my laptop, I will spend 1 minute researching companies I might want to work for.”
ACTION STEPS (5 minutes):
- Pick one of your Key Results and brainstorm a tiny habit that will bring you closer to achieving it.
- Link that activity to an existing habit in your routine – for example, “After I finish brushing my teeth, I will floss one tooth.”
- Create this tiny habit as a task in your app.
- Make the task recurring (directions on how to do this in Todoist here)
- Rinse and repeat steps 1-4 for each of your Key Results.
Prioritize your goals to live your best life
You’ve created a system that’ll help you organize and progress towards your goals. At this point, it’s easy to get caught up in getting things done, and easy to forget to step back once in a while.
Earlier in this guide, I asked you to brainstorm an OKR based on what you enjoy doing, or a skill that you’d like to improve on. Now that you’ve done so, it’s important to make sure you set aside time to self-evaluate.
You can do this through what the OKR system calls Quarterly Review. Every quarter, you should grade each of your Key Results, then average those grades to create an Objective grade. By doing this, you can see progress to your goals, so you appreciate where you are and where you’ve been. At the same time, you can adjust goals that are too easy or too difficult, so that you can keep challenging yourself without getting discouraged.
As you spend time using this system and gathering more data on your progress, you can also start drilling down into what’s actually important and meaningful to you on a personal level. Quarterly Reviews create a beautiful cycle that lets you evaluate and adjust your life plan, guilt-free.
During your Quarterly Review, you will grade your Key Results for progress between 0% to 100%. The sweet spot for a Key Result on is between 60% to 70%.
A score lower than this might mean that your Key Result was too ambitious or you didn’t prioritize it. That means it’s time to evaluate it and adjust its difficulty to make sure it’s actually achievable and aligns with your Objective.
A score above 70% means that you should raise your sights and make your Key Result more ambitious. If you completed it entirely, grade it 100% and swap it out for a new KR that also advances the Objective.
Once you’ve graded your KRs, take a closer look at the Objective with the lowest average grade – the one you made the least progress on. Time to dig deep. Ask yourself the following questions:
- Why did I set this Objective for myself?
- Will accomplishing this bring me joy?
- Why did I not score higher on this?
- Did I make this a priority?
- Should it still be be a priority?
From there, decide whether you should continue working towards this Objective, or replace it entirely.
ACTION STEPS (25 minutes)
- Download my free OKR grading template by clicking here.
- Fill it out with your drafted OKRs.
- Set a quarterly reminder in your universe app to review your OKR grading template for progress.
- Set a quarterly reminder to review lowest-scoring OKR, deciding whether you should keep it, adjust it, or replace it entirely.
Go forth and conquer
We’ve gone over the tools you need to capture your goals and cross things off your list. Having a universe app is essential to keep it all in one place.
Then, I shared my twist on the OKR System, taking a goal-setting system typically used by fast-moving companies and repurposing it to powerful effect on your personal life.
We went into how tiny habits, consistency, and specificity are key to executing on your objectives over the long term.
Finally, we introduced the idea of Quarterly Review, to help you evaluate and adjust your plan on a regular basis.
By bringing all of these pieces together, you’ll be able to achieve consistent progress towards your objectives – waking up every day with purpose, crushing your goals, and spending your time the way you want to.
“Where do you see yourself in five years?”
The next time someone asks you this question, think back to the OKRs you’ve set. You know the answer already. It’s time to go for it.