Are You a Time Prisoner?

It’s 10:12pm and you’re still working.

You were constantly interrupted today by a string of emails, Slack notifications, last minute requests from teammates, and clients that “just needed 5 minutes to chat”.

You had a long list of priorities you needed to get done, and now that it’s finally quiet and your family’s asleep, you can try to get things across the finish line.

You glance at your email and realize you’ve got 62 unread messages.

Overwhelmed again, you open up Instagram and just start scrolling, walking to the kitchen to finish off that pint of ice cream.

You get in bed just after midnight, 11 tasks unfinished, and feeling like a failure.

The next morning you wake up and jump right on your phone, so many emails still unread.

Feeling the stress already, you skip your workout, hop on your computer, and just start working. Somehow you always come up short and feel little got accomplished.

And the vicious cycle continues.

If this is resembles you in any way, I’m sorry to tell you: you’re a Time Prisoner.

And I’d like to help you escape.

Jump to the bottom of this article for your escape plan, otherwise keep reading to find out if you’re a Time Prisoner.

How to Know if You’re a Time Prisoner

I get it. No one wants to be called a Time Prisoner.

We all want to think we have agency and have a choice in the matter. But reality is our friend. It is step #1.

So let’s face reality.

Answer the questions below honestly, and see where you fall.

1. Do you feel overwhelmed when you look at your to-do list?
2. Are you constantly interrupted to requests from others via phone/email/Slack/Teams?
3. Do you frequently work late when it’s “quiet”?
4. Do you resent the stakeholders in your life that are giving you things to do?
5. Do you tear yourself away from work at the end of the day, stressed out by all the things you DIDN’T get done?
6. Are you unable to take a break or rest on a weekday?
7. Do you feel like your days are unproductive, even when you're busy?
8. Do your calendar or to-do list cause you any of the following: overwhelm, anger, stress, misery, broken relationships, pain or health issues?
9. Do you “rest” with Instagram, Netflix, or ice cream?

How did you do?

I’ve got good news and bad news for you.

Bad news first: if you answered “yes” to even one question above, you’re a Time Prisoner.

And here’s the saddest part: you’re also the warden of your Time Prison. In all the situations described in the questions above, you are 100% responsible for your dysfunctional relationship with time.

You have created or allowed the constraints on yourself to shape your Time Prison in each situation. Let me demonstrate:

1. Do you feel overwhelmed when you look at your to-do list? —> You’ve allowed yourself to use a system to manage work that creates stress for you.
2. Are you constantly interrupted to requests from others via phone/email/Slack/Teams? —> You’ve chosen not to create boundaries and systems to allow others to get what they need from you without you being constantly available.
3. Do you frequently work late when it’s “quiet”? —> You’ve allowed yourself to work on everyone else priorities during the day, and have not created a system to allow you to make your priorities happen during your working hours.
4. Do you resent the stakeholders in your life that are giving you things to do? —> You’ve allowed yourself to get overwhelmed without a system to manage work.
5. Do you tear yourself away from work at the end of the day, stressed out by all the things you DIDN’T get done? —> You have not done the work to understand your actual capacity, so you have unrealistic expectations for what you can accomplish, making you feel like you failed.
6. Are you unable to take a break or rest on a weekday? —> You allow yourself to just keep working, because you don’t understand your actual capacity. This leads you to feel constantly, so you can’t stop working to take a break or truly rest.
7. Do you feel like your days are unproductive, even when you're busy? —> You are allowing yourself to work on things that are not your priorities.
8. Do your calendar or to-do list cause you any of the following: overwhelm, anger, stress, misery, broken relationships, pain or health issues? → You allow yourself to start another workday with a calendar and to-do list that don’t create freedom for you. By not upgrading your tools, you are accepting these painful results.
9. Do you “rest” with Instagram, Netflix, or ice cream? —> It’s your choice to structure your day to lead to this type of “rest”. And this is not resting. This is buffering. You’re simply checking out and getting out of your head for an hour. You’re not actually recovering.

Here’s the good news! You’re the warden of the prison, and you can change the rules.

The Alternative: The Freedom of Being a Time Boss

Here’s another possible reality:

It’s 8:00am on Monday and you jump right in to the first 3-hour task your Time Boss planned for you (spoiler: you ARE your own Time Boss).

The task has a clear definition of done, so you know exactly what to do, and get after it.

Even better, your Time Boss last week in their Weekly Planning Meeting prioritized this one task for you for the next few hours so you can focus entirely on this important item, leaving you with total peace and confidence to make this task happen.

No notifications are interrupting you, because you’ve done the work to clean up your notifications, confident that your VIPs can get ahold of you for urgent items, otherwise everyone can wait till your Whirlwind time later (aka your daily buffer to deal with reality). You are peaceful and focused.

You complete the task 15 minutes early because you estimated well, and you take a quick stretch break and walk the dog. No stress. All peace.

11am hits and you glance at the rest of your calendar, where you find your Time Boss has crafted a realistic plan for the rest of the day, so you simply get started on the next calendared task.

After a great afternoon, including a few hours of Whirlwind where you replied to all emails, returned all calls, and responded to all Slack messages, you close your laptop at 5:46pm. The only thing you feel: satisfaction. You crushed a great day of work, one that was customized and rightsized just for you, and it’s time to rest and recover with those who matter most to you.

Sounds amazing, right? Maybe too good to be true?

It’s real. And the growing community of Time Bosses are proving it.

Hear from actual Time Boss Alumni:

•  "I’m way less stressed. My progress at work is more strategic, enjoyable, proactive and sustainable where it used to be reactive."      Daniel Decker
• "This content was a total game changer for me. Time Boss has truly increased my productivity so much."      Anj Bourgeois
• "I perpetually felt behind. I needed to think about my time and capacity differently. The cohort was life giving and creative-stoking, hearing other people's perspectives. I was able to go on vacation and not pick up my computer."      Jill Chun

Imagine escaping time prison for good and living into your God-given, highest potential. Where clarity, freedom, passion and peace are available in abundance while you crush your highest priorities.

A world exists where you’re in control of your calendar. Where you are focused on your most important items and ignore the rest, where you feel like you’re consistently making progress toward the things that are important to you, and where you quickly see wins and get the results you want.

Make your financial, creative and personal dreams become a reality by upgrading your habits and mindset around time and promoting yourself from Time Prisoner to Time Boss.

No time like the present, let's get started.

Getting Started: A Time Boss for Your Future Self

The Time Boss model is based on this idea: you are the boss of your future self.

When you take time to plan and set up your future self to be successful, you are a Time Boss.

Your future self is simply responsible to make the plan happen, just like your employee in the example above.

More good news: I’ve spent 15 years iterating on this model to make it as simple as possible to get started.

Your Escape Plan :: The Time Boss Habits

Prior to 2017, I was in Time Prison for over a decade, and I had no idea how to escape. It took me 15 years to dig my way out with a metaphorical shiv, testing and iterating on literally hundreds of different methods.

What took me over a decade of iterating, you can unlock in weeks. Every month, cohorts of Time Prisoners jump into a Time Boss 6 Week Coaching Cohort, and get daily reps on the Time Boss habits outlined below. 95%+ report making more progress on their priorities than they did before, and 100% report decreased anxiety/stress and increased peace.

Aka prison break 🙂

Ready to break out? Let me show you the way.

Weekly Planning Meeting

• When? :: 1 hour weekly, prior to the beginning of your next work week
• Why? :: By planning weekly, you become the “Time Boss” of your future self. This allows you to create a realistic plan, prioritized to match your strategic goals and values, that your future self can simply make happen. By creating a realistic plan, and mapping it to your calendar, you reduce overwhelm, and dramatically increase your commitment to protecting your priorities. Stress goes down, progress on priorities goes up.

Daily Review Meeting

• When :: 15 minutes daily, end of your work day
• Why :: You did the work to create a realistic plan in the Weekly Planning Meeting. The Daily Review Meeting is how you maintain commitment to the plan. By paying attention to your results daily, you can make the adjustments needed to make the plan happen, and you have a backstop in place in case a day goes sideways, preventing you from an emotional tailspin, and allowing you to recover the next day.

Are you ready to escape Time Prison?

On my own, it took 15 years to escape Time Prison. I would have given my left pinky finger to have someone show me the Time Boss Habits as a way out.

Change can happen fast. It doesn’t take months or even weeks. Just a few hours a day for lifelong habits and changes.

Is 2024 the year you make a break from Time Prison so you can start loving the life you’re living?

Join me on a free monthly masterclass, where I share the details of how to run a Weekly Planning Meeting and Daily Review Meeting like a Time Boss, and help you take the first steps to escape Time Prison.

Sign up for our upcoming Free Masterclass: The Time Boss Weekly Operating System

The first 10 people to sign up will receive a BONUS 30-minute coaching call with me ($125 value!). Sign up here!

P.S. If you’re a team leader and you think you might have a team full of Time Prisoners, feel free to invite your full team to the workshop. Time Boss for Teams is revolutionizing the work experience across for profit and non-profit teams.