Inside Kendra Wright’s Planning Process

Planning is a very personal process. We all have a different process to plan what we’re going to work on and get accomplished, and what goals we will focus on. That’s why I always find it interesting to dive into inspiring people’s planning process. Earlier last year, I invited Kendra Wright, creator of the Year of Fear project on the blog. Since, I’ve discovered that Kendra has a very interesting take on planning and incorporating adventure into her weeks. She gracefully agreed to share her planning process with us today. Let’s dive in!

Kendra, welcome back to Productive Happiness! Can you share with us what life design is, and how can we integrate it into our daily lives?

Life design to me is making a conscious choice on how we will spend our time versus totally winging it like many people do. Putting your priorities on your calendar before the demands of the world take over. Whereas many people let others rob their best time, energy and attention. Then, invest whatever time is left into their goals, ideas and relationships. I do that the other way. My priorities on my calendar first. Not others.

You talk about scheduling fun first. Can you tell us more about that?

On Sundays I make my schedule for the week. I always make sure to schedule in something fun before the chaos of life takes over. I don’t “hope” that I’ll have time to do something fun or interesting, I plan for it.

You use your calendar in a very special way to plan adventures and comfort zone challenges. Can you describe that process?

Every Sunday morning, I have a set planning appointment with myself. I use that time to get clear on my priorities before the chaos of the week starts and make sure that I schedule a minimum of one thing that will create a memory that week. It may be a challenge from my comfort zone list, trying out a new hobby, or seeing a new event or show in town. The key is to have a weekly time you can review and plan where you’ll have no distractions, good energy and a list of what is important for you to make your week worthwhile. For me, that means doing something new, creative or interesting at least once a week.

How different is this process from your business planning?

Personal planning watches out for my personal life and my goals there (such as time with friends, self-care, new experiences). Business planning hinges on, what deadlines do I need to hit this week and what goals have I set in my business. Most people tend to typically plan for work only (what do I need to get done this week). My weekly planning appointment for my personal life (on Sundays), ensures that I have space and time to also have a LIFE, not just work.


Can you tell us about color coding and how it helps you with work-life balance and planning?

I plan digitally but you could apply this to a paper calendar as well using highlighters. I choose colors for the big areas in my life:

My business = Blue
My personal time = pink
Self-care (morning routines, lunch, restorative activities) = green

I color code my week so that I can see if I have a lot of huge work projects (blue) coming up and no fun planned (pink), I may need to schedule some off-time or block off an evening to recoup.

You can see visually in an instant what the balance of your week is.

Kendra Wright planning process
A glimpse of Kendra’s calendar and color-coding

Here at Productive Happiness, we often talk about quarter planning and goal setting. Why do you think that planning your goals in 90 days increments is more effective than planning yearly goals?

When we plan in yearly sprints, the deadline feels far away and we aren’t motivated to take action. We overestimate what our future selves will do. If you plan in 90 day sprints, the timelines are long enough to set decent goals, but short enough you have to get to work right away or you’ll be able to see you aren’t making progress. It’s also less intimidating to break down larger goals.

For example, if your goal was to grow your email list to 10K subscribers by the end of 2018, that goal can leave you feeling overwhelmed and unsure of where to start.

However, if you plan in 90-day sprints, your 90 day goal would be 2500 subscribers. All of a sudden I can pick my jaw back up off the floor and get to work.

How do you choose what goals to work on when you plan your 90-day sprints?

What is the goal(s) that if I hit it would make everything else in my life easier or unnecessary? I wish I had thought of that brilliant question myself, but I did not. Read The ONE Thing by Gary Keller and focus is much easier in goal setting.

How does rest and recovery play a role in your life at the moment? How do you recharge after a 90-day sprint?

It varies. Usually, a week off! Or, even during the sprint if I tackle a large goal, I may even reward myself with a smaller reset such as a massage or a Friday off work.

Kendra working from the Bahamas

What role does self-care play in your productivity?

Self care is an enemy of burnout. The more I take care of myself and set boundaries, the better my entire life is.


In a recent podcast episode, you talked about the Bingo card of good habits. Can you tell us a bit about that and where it comes from?

There is a set of habits we all have that keep us sane: getting enough sleep, taking a long hot shower, doing yoga, making time to read for a few minutes before bed, etc.

When you have a bad day, or you’re going through a tough rut in life, imagine that a list of your top 10 healthy habits that you do when you’re operating well are scribbled on a bingo card.

To move through ruts, burnout or hard times in life, make it your mission to cross as many of these habits off in a day.

There is one habit though that is disproportionately better than the others. For me, it’s listening to motivational videos first thing in the morning. Maybe yours is hitting a goal class. Whatever that habit or activity is, I call that your “free center square.” And you really need to cross that habit off as often as possible – especially when you’re going through a heavy work load or life is throwing you tough stuff.

So, when you’re feeling drab, try to get a bingo — as many of your healthy habits in as possible.
And on the days when you can’t do that – at least cross off the center sqaure – that one habit that centers more than all the rest.


What is one advice you would give to a fellow recovering workaholic to add more balance into their lives?

Starting small is better than not starting at all. Plan one leisure night per week where you won’t allow yourself to bury yourself in your work or the demands of others. And when that night comes, do whatever you want without guilt: dive into Netflix, read, go out with friends. Whatever you want. The rest of your week, you can work yourself to death, besides this one night. No guilt allowed.


Thank you Kendra for hopping by and sharing your planning process with us! If you’d like to see Kendra’s planning process in action, head over to her blog and watch this special video she filmed where she takes you through it step by step! What is your takeaway from Kendra’s planning process? Share your answers in the comments below!

Kendra Wright


Kendra Wright is a blogger, speaker, and location independent entrepreneur. Since creating The Year Of Fear Project in 2013, she has completed over 850 self-assigned comfort zone challenges. Kendra specializes in teaching others how to break through fear and uncertainty, take consistent action on meaningful goals, and embrace the rebel they were born to be. Visit her site at heykendra.com

You may also like