Create Permission to Work Differently

The rules that we’ve followed in our careers and professional paths have led us down an unsustainable and ultimately dangerous road. Burnout, distractions, scarcity and overwhelm.

So we need to play a different game.
To live by new standards.
To subvert societal expectations.
And work differently.

And as rule followers, the best way to change how we behave without guilt, fear, or self-doubt, is to feel like we actually have permission to change.

Change starts when we create new definitions.

Here are 5 questions to consider asking yourself to give yourself permission to work differently. If this were a workshop, I’d ask you to think about this as an activity to actually do. Answer these questions. Start by writing what comes to mind immediately but sit with your answers and continue to add and edit them. Your answers will change depending on the time of year and your phase of life.


What does it mean to have a good day at work?

You get to decide how you evaluate your worth. It’s not always getting everything done. It could be about effort. Showing up. Doing something important. Surprising yourself. Supporting others. Learning something. Just one hour of focused, deep work. You don’t have to evaluate your day based on productivity.


What is “enough” work?

It’s easy for work to take up your whole day… and then into your nights and weekends. So how will you judge what enough is for today? That you can close your computer confidently and guilt free because you did enough? Is it based on time? At 5pm wherever you are, it’s time to stop (bankers hours). Or are you working until the task is done? (Firefighter hours) Is it doing your most important task? Or an empty inbox?


What is your ideal day?

Sometimes we just show up to work and go through our day like a robot. Or zombie. Or whatever non thinking analogy. But if you know that your best day includes exercise and a prepared lunch and a few minutes of social connection before a meeting starts. Maybe it’s having quiet alone time in the morning and meetings in the afternoon. When you’re clear about how you work best, it’s one step closer to actually getting it (or being the one to make it happen).


What distractions can I cut out?

There are always things that will come up that will get in the way. What can you do to take control of your time and attention a little bit more? Can you put your phone away? Or block certain websites? Turn off Slack for an hour at a time or schedule checking email for 3x/day. Having more autonomy in your time is going to make a difference in how you feel about your work and allow you to work differently.


How do I want to show up to work?

We get disregulated and emotional at work. Which means we lose our patience and focus, we feel anxious and jealous and petty and angry and hurt sometimes. But if you had a clear intention about how to show up you’ll more easily be able to take a deep breath and regulate yourself. Is it about being easy to work with? Or supportive and helpful? Playful and fun? Do you want to seem smart? Or a stoic leader?

These questions can light the pathway towards getting clearer definitions for yourself about where you want to go. And those definitions give you permission to change the way you work.

Stay focused out there.


Caveday is a company aimed at improving your relationship to work. We write regular posts on Medium and send out monthly newsletters with productivity tips, life hacks, and recommendations. Sign up for the mailing list here.

Jake Kahana is a cofounder of Caveday. Sign up for his personal emails, called “The Email Refrigerator” here.