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5 Annual Review Questions to Help You Flourish

How to define what a life well-lived means and how to build it.

Key points

  • By asking introspective questions, we can develop clarity on what a life well-lived means to us.
  • By keeping the life we want to live in perspective, we can take deliberate action to build it.
  • By regularly taking an inventory of our progress and direction, we can course-correct if we get off track.

Annual reviews are popular, but most miss the mark because they ask generic, superficial questions. They don’t get to the heart of what a life well-lived means for us or how to build it. The point of any review is to take an inventory of two things:

  • How you spent your time, energy, and attention.
  • How well the way you allocated those resources made your life better.

If you want to develop clarity on what you truly want out of your life and business, you need to ask questions that get to the heart of what it means to live a good life and do work that matters.

5 Questions to Ask Yourself

Here are five questions I ask myself and use with coaching clients that may help you develop clarity on how to build a life aligned with your values, so you can flourish.

1. “If this had been my last week alive, am I satisfied with how I spent my time?”

Most of us live for “someday":

  • “Someday, I’ll travel.”
  • “Someday, I’ll write that book.”
  • “Someday, I’ll spend more time with my kids or partner.”

But one day, you’ll be out of “somedays.” This question helps pinpoint anything you let into your life that drained your energy or meaningful things you put off.

2. “What would I do if I didn’t need the money?”

Put another way, are you only working for a paycheck even though you’re miserable, or do you love the work you do?

Money and meaning aren’t mutually exclusive; it’s possible to make money doing meaningful work.

When you love your work, you’re tapping into intrinsic motivation, which is an aspect of human flourishing.

3. Am I practicing memento mori?

Memento mori means “remember death.” It reminds us to practice deep gratitude for what we have while we have it.

  • You won’t always live close to your best friends.
  • You won’t always be able to call your mom.
  • You won’t always be in perfect health.

Life is fleeting and precious; remember that it will end.

4. Where am I overcomplicating things?

It’s easy to waste time preoptimizing by going down YouTube rabbit holes and designing the “perfect” systems and business plans, but being busy isn’t the same as being productive.

Most of the time, this busywork is a distraction keeping us from taking action. Remember: Progress over perfection.

5. Where am I letting the Four Horsemen of Fear stop me from doing meaningful work?

Most of us have the potential to have a way bigger impact than we give ourselves permission to believe, but limiting beliefs hold us back. Learning to identify where our limiting beliefs and self-sabotaging behaviors are manifesting in our lives is the first step to overcoming them so we can flourish.

Wrap-Up

These questions are great to add to your journaling habit or to ask on a weekly or monthly basis, not just once a year, because the more regularly you take an inventory of your progress and direction, the faster you can course-correct if you’re off track.

Parts of this post also appeared here.

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