Making Your Work Life Work

Depending on a number of variables, you’ll spend anywhere from a quarter to a third of your life at work. It’s no wonder researchers, educators and journalists have continuously published articles, both scholarly and popular, on the implications of having an imbalanced work life and how you can take practical steps to prevent your work from taking over your life.

You can find thousands of videos and pieces of writing about quitting your job and leaving it all to pursue your passion. I want to be truthful by saying that I love that mentality, but most people are not in a position where they can stop what they’re doing, take time off, find a new job, start their own business or turn their hobby into a career. The majority of us will have to make the best of the situation we’re in.

Making sure your job and the type of work you do brings out the best version of yourself is a real challenge and one that is worth your time and energy.

We all need an “assist” sometimes to help us kick-start this process of making a more satisfying, conflict-free and healthy work life for ourselves. This is why having a strategy you can look to might be useful. Slightly oversimplified, you can break down what you need to do to reimagine your work life into three stages.

Stage One: Reflection

In the first stage, you want to reflect on the good and the bad in the short and medium term. The goal is to increase your awareness with regards to yourself, the people around you and the environment you work in. Thinking about the entirety of your past and future can be overwhelming; that’s why narrowing your focus to a specific time frame can be helpful and will make it easier for you to remember notable work experiences. For instance, you might choose to limit yourself to reflect on just the last month or quarter.

We refer to this type of reflection as “utilizing your history.” Here, it’s all about valuing moments of achievement and failure. When we give value to those moments, we can recast them as opportunities for learning or intervention. Reflecting and making use of your past successes and failures is a good habit to get into, even when you’re not trying to reconfigure your work life.

Try It Now: Utilizing Your History

Get out a sheet a paper and rotate it to landscape. Decide on a time frame you want to reflect on, draw a timeline across the sheet of paper (halfway down) and label each end.

Now, in the top half of the sheet, plot your achievements, favorite projects, or moments where you felt appreciated, joyful or engaged. Work backward, pulling your calendar up if you need to jog your memory. Once that section feels adequately filled out, move to the bottom half of this personal journey map.

Plot out any pitfalls, undesirable projects, problems, failures or moments of disappointment. From here, spend time with both halves of this journey map and highlight anything you’re particularly proud of, significant disappointments, things you don’t understand or ongoing issues that are unresolved.


Stage Two: Fresh Perspectives

The second stage requires that you get a fresh perspective on your issues and then think generatively to develop ways to enact change.

Yes, great ideas come from individuals and teams but what about pairs? One-on-one partnerships have a ton of potential for coming up with great ideas and should not be underestimated—think Ben and Jerry, Paul and John or Tina and Amy. Working with a trusted colleague or friend will help you determine where any stress might be coming from and where you should make adjustments. In many cases, you’ll also gain a sense of affirmation, which is a major human need, from performing this activity.

The problems and solutions that I’ve seen surface when facilitating this activity have significantly varied. One workshop attendee identified that she was struggling to stay motivated while working from home. Another participant found that they were neglecting to incorporate the feedback their administrators had repeatedly told them. Equally insightful, one person found that they had gotten almost too comfortable in the position they were in and no longer felt challenged in a way that encouraged growth and curiosity.

Try it now: Developing Insights + Generating Ideas

Schedule at least one hour with a trusted colleague or friend. Talk them through your personal journey map making sure to spend more time with the low points or high points you highlighted.

To help them understand what you’re going through, give them context, share a story or specific example, and why you plotted these highlighted items where you did. If they are willing, ask them to repeat what they just heard back to you. Essentially, you’re asking your partner to be an active listener while you practice being a good storyteller.

With your partner, try defining your struggle using this Madlib: I am experiencing/feeling/being challenged by [insert a specific and ongoing issue, task, relationship or blockage that you’re struggling with here] because [write why this thing persists or exists]. Below, you’ll see a real example from the first time we tried out this Madlib with a group of educational administrators.

Once you’ve workshopped this challenge statement, brainstorm, with your partner, ideas and strategies for tackling this challenge. When you’re generating ideas, you might try out these prompts to enable some creative thinking:

  • What is the easiest thing I could do?
    Example solution: Purchase a more comfortable desk chair.
  • What is the most extreme thing I could do?
    Example solution: Ask your supervisor if you could switch to a four-day work week.
  • What is an unexpected resource I might take advantage of?
    Example solution: The park across the street for a team meeting.
  • What would [insert someone you’ve always looked up to] do?
    Example role models: Ruth Ginsburg, Morgan Freeman or Dieter Rams.


Stage Three: Pre-Mortem Thinking + Implementation

In the third and final stage, you should make contingency plans and leverage newly discovered resources as you begin to incorporate the ideas you and your partner brainstormed. Enacting change at work can be difficult. You might need to try out a few of the ideas before you find the one that improves your situation at work—so, bank all the ideas you came up with and pull another one out if you see that what you’re trying isn’t increasing your happiness and satisfaction.

I’d encourage you to be positive and action-oriented as you begin to experiment with different solutions. However, it doesn’t hurt to anticipate negative responses or push-back by doing a little bit more strategizing. Envisioning your idea failing, why it failed, and how you might respond or how your co-workers might react could save you some skin and will keep you in a productive mode as you move onto another idea or evolve the one you’re trying out.

Also, take the riskiness out of what you are doing by rehearsing your idea with your partner, a friend or a small trusted group of coworkers. Just like an actress on Broadway doesn’t step onto stage opening night without practicing their role, you should practice what you’re going to say, the routine you might follow, what you might facilitate, or how you might react.

Try it now: Action Planning

Identify which idea you generated will most likely solve your problem. Give yourself a timeline that encourages making incremental changes. We suggest making a plan for change in the next three days, three weeks and three months.

Begin this plan by documenting what idea (or portion of an idea) you want to pilot. Then, list what are some indicators of success. In other words, how would you know if it’s working? Now, think ahead by considering what might hinder your plans. Are there any foreseeable obstacles? Following that, what’s your contingency plan? Or, what will you do if your idea fails? (You’re doing great!)

After your time planning three days of change, the next step is to create your three-week agenda and then your three-month agenda. No matter what happens during those three days, you should be evolving and expanding how you’re enacting change in your work life. Try to do this planning in as little time as possible. It’ll benefit you to maximize your time doing something and learning from your mistakes, rather than just endlessly planning.

Make sure the ideas you want to implement and the changes you want to make are memorable, not a massive risk (meaning, little time and money are required) and can happen within the fixed time period (three days, three weeks or three months).


Whew. Nice work!

Adding intentionality to your work life is no easy or—in some cases—enjoyable task. It’s an iterative process where you make incremental changes, learn from your mistakes and then try again. Don’t get frustrated! Keep iterating, asking for help and thinking creatively.

Through this effort, you’ll feel better mentally and physically. You’ll eliminate stress and help get into a more satisfying and healthier way of working. Make sure to thank all those who helped you out along the way and don’t forget to celebrate! Eat some Little Tokyo mochi ice cream in Los Angeles, go for a hike on the Vermillion River if you are in Chicago or check out that brewery in Red Hook if you are with us in New York.


A song to do some reflection to:
Sanza nocturne by Francis Bebey

A song to do some planning to:
Green Onions – 45 Version by Booker T. and the MG’s

A song to move your body to:
I Woke Up Today by Port O’Brien

Blog inspiration:
WorkLife with Adam Grant (the podcast)
Achievement Habit by Bernard Roth
Realizing Empathy: An Inquiry Into the Meaning of Making by Seung Chan Lim
Beyond Nine to Five: Is Working to Excess Bad for Your Health? by Lieke L. Ten Brummelhuis, Nancy P. Rothbard and Benjamin Uhrich
Coping Skills: Tools & Techniques for Stressful Times by Dr. Faith Harper

Timothy Moore
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