Evaluating yourself doesn’t need to be painful

Feeling stuck? Practical ways to achieve personal goals

Part 2 in a series of posts about designing new life chapters

As I mentioned in the first post in this series, I am currently taking an exploratory year and, being a designer, I put a lot of thought into how to (lightly) structure my time. I am approaching the year as a design project, applying best practices from the design world to my personal life.

Below are three design methods I find particularly helpful for personal growth. For each method, I include examples from designing my exploratory year. But these methods can be used at any time — whether or not you’re taking exploratory time — for professional projects, personal projects, or just promoting general life growth.

Method 1: Success & Failure (a one-time exercise at the start of a project)

Here’s how it works:

Before your project starts, imagine it has just ended (bear with me). Imagine it was a huge success. What does the world look like now? What things are now true because the project was a success? Write these down.

Example: My exploratory time was a success because at the end I…

  • am working on something creative & fulfilling
  • have a vision for a sustainable, flexible life
  • feel healthy
  • have learned one or two new skills
  • am doing okay financially

Now, put on your pessimist hat (this one tends to be easier). Imagine the project ended and it didn’t go well. Imagine it was a failure. What does the world look like now? What are all the ways that your project could fail? Write these down.

Example: My exploratory time was a failure because at the end I…

  • spent more than I budgeted and have no more savings
  • spent too much time worried, anxious, or depressed
  • am no closer to figuring out what’s next
  • didn’t learn anything new
  • didn’t give back to society

After you write these down, put them away.

This seems like a simple exercise, but it is incredibly powerful. It forces you to articulate your greatest hopes and worst fears. For projects with many stakeholders, it allows the team to voice collective fears and intended goals.

You can return to these guidelines throughout the project — especially at the end — to evaluate success, but the true power is in their articulation. When you write down your goals, they tend to end up happening. This isn’t magic — psychology tells us we’re likely to follow through once we make a commitment — but it feels like magic every time.

Method 2: Quarterly goals (every three months)

At my former company, Opower, we implemented a goal-tracking method — used by Google, Intel, and other tech companies — called “Objectives and Key Results” (OKRs). At Opower, I found them to have mixed value, depending on how teams used them, but they have been incredibly useful when applied to my personal life. (My former colleagues find this hilarious — like I’m writing performance evaluations for fun — but, they work.)

Here’s how I use them:

Think about all the areas in your life where you want to grow. These are your “areas of focus”.

Example: My areas of focus are:

  • Love/connection (includes relationships, community)
  • Creative health
  • Physical health
  • Spirituality
  • Giving back
  • Career

For each focus area, come up with one high-level goal you want to accomplish this quarter. If you have something specific, great. If not, you can keep it very general. These are your “objectives.”

Examples of objectives, from more general to more specific:

  • Creative health objective: Grow creatively
  • Career objective: Stay lightly connected with professional life
  • Physical health objective: Learn to do a handstand in yoga

For each objective, choose 3–5 actionable items that you can do during the next quarter to help achieve that objective. These are your “key results.” The important part is that they are actionable, meaning they can be crossed off a to-do list.

Examples of key results:

Objective: Grow creatively

  • Finish two paintings.
  • Sign up for a writing class.
  • Make something for a loved one every week.

Objective: Stay lightly connected with professional life

  • Speak at one conference.
  • Teach one class or workshop.
  • Update my website.

At the end of the quarter, read over your goals. You can be formal about it and “grade” them, assigning a percentage complete to each objective. Or you can just use this as a learning experience to see how your intentions have changed and how much your “key results” matched up with what you actually spent time on. After assessing, start again. Write new goals for the next quarter.

There are many other approaches to goal-setting besides OKRs (The wheel of life is another good one.). The important thing is to find one that resonates with you and that you will actually use. For some people, OKRs are overly specific and cause stress. Defining your areas of focus and doing a high-level success/failure projection may be all you need.

When writing goals, there are a few techniques that will make it more likely for you to follow through with your intentions. Make sure your goals are:

  • Actionable. (as mentioned above) Always associate your goals with clear, do-able, next steps. “Grow creatively” is a helpful objective to set the stage for your focus, but “Create two paintings” is a more appropriate short-term goal because you can act upon it.
  • Achievable. Don’t set yourself up to fail by choosing a goal that is virtually impossible to achieve. There’s been a lot written on the power of starting with baby steps to achieve lasting change. For example, instead of trying to “meditate for two hours every day,” aim to “sit on cushion for at least one minute every day.” For me, the quarterly cadence of OKRs works well, because three months is the perfect amount of time for me to accomplish bite-sized goals. More often would feel like overkill, and less often wouldn’t be as motivating. Pick a timeline that works for you.
  • Accountable. You will be much more likely to follow through if you share your goals with someone else (public commitments principle). In the workplace, OKRs are written with your team and reviewed by your manager each quarter. At home, you can review your goals with your partner or a friend or relative. You could also create an “advisory board” — a small group of like-minded people who all review goals for each other. I keep my OKRs in a Google doc and share it with 1–2 people each quarter.

Method 3: Morning Pages (daily)

Here’s how it works:

Buy a journal. Every morning when you wake up, before you immerse yourself in screens, spend 20–30 minutes writing. Write without stopping to think, getting out every thought that comes to your mind, be it silly, senseless, or self-reflective. You can always write, “I don’t know what to write,” over and over, if that’s what you’re thinking. Don’t judge what you write or re-read the entries after you write them.

Morning pages is a technique from the Artist’s Way, a 12-week book/course that helps you reconnect with your creative self. It’s one of the techniques from the book I continue to do, as I find it helpful to slough off all the chatter in my mind before starting the day.

Good morning, pages (and sun)

Besides Success & Failure, OKRs, and Morning Pages, here are other methods you may find useful:

  • Create a Wheel of life.
  • Write a Personal Mission Statement.
  • Read the The Artist’s Way. This book is a 12-week approach to reconnect with your creative self. Not all the exercises may resonate with you, but the parts that do could be very eye-opening. (I discovered Morning Pages here.)

There are countless others — do your own research, talk to your communities, make up your own. All that’s important is finding something helpful to you.

Hopefully, some of these methods will provide enough light structure to help you focus your explorations. Next: In the next post, I walk through techniques for figuring out where to start exploring.

If this was helpful or interesting to you, please click the heart. When you do that it actually goes right to my real heart!


  • Photos: Scale is at the Museum der Dinge in Berlin; Mountain is sunrise seen from Adam’s Peak in Sri Lanka.
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