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What to Do During Your Career Retreat

What to do during your career retreat _ Red Cape Revolution

So you’ve decided you want a career retreat.

It’s a gift of time you’re giving yourself to look at where you’ve been, and where you’re going.

That’s pretty awesome.

And if you’re retreating all by yourself, you’ve probably already completed the first big step: getting your career retreat scheduled and organized.  (If not, this article and the downloadable planning tool here will help you DIY your career retreat.)

Great!  . . . now what?

Whatcha gonna DO during your career retreat?

Ummmmm. . .

Don’t fret. Here are tools to help you plan your agenda, because planning is a essential to make this investment pay off –even if the only attendee is YOU.

(After all, that’s a pretty influential person in your career’s success.)

First, Review What You Want to Accomplish (& Be Realistic)

If you’ve followed the planning guide here, you already have answers to these questions:

  • The main focus (or question I’d like to answer) in my retreat is:
  • When I have the answer to that question (or have clarified my focus), I’ll feel or know . . .

As you create your structured agenda, look at your answers again. Do those goals feel reasonable within the timeframe you have? If not, how can you tighten the focus or make the question smaller?

Don’t overwhelm yourself by trying to do too much. Rome wasn’t built in a day, but they were laying bricks every hour.

Your goal is positive, forward progress–just one step along the path.

Now, Divide Your Retreat Into Three Equal Parts

Three is a magic number because the brain likes simple.

So breaking your time into three parts often works best, especially if you have a day or less. Here are the three I recommend:

  • Part 1: Where are you now, as it connects to your area of focus or question?
  • Part 2: Where do you want to be?
  • Part 3: What’s the simplest next step to get closer to where you want to be?

Let’s dive deeper into each of these parts.

Part 1: Where are you now?

“What do you mean, where am I? I’m underutilized/overworked/underpaid/overstressed . .  .why’dya think I need the freakin’ retreat anyway??”

Ohya, I get it.

Because we think our current state is obvious, we skip over the “where am I now” question.


But is it obvious? What’s REALLY going on?

Here in your retreat time, know you’re safe. You can say and think things you wouldn’t in your normal life. (In fact, you must.)

Consider that you’re being invited (by you, that generous human) to be perfectly honest.

Because until you start telling the truth about where you are, you’ll keep going in circles.

Here’s a strategy to help you find your truth: the persistent why.

Steal this strategy from the curious toddler, and keep asking yourself why. For example:

  • I need to leave my job.
  • Why?
  • Because I’m not happy.
  • Why?
  • Because my boss doesn’t treat me with enough respect.
  • Why?
  • Because he doesn’t understand how I can help the company.
  • Why?
  • Because I haven’t really tried hard to tell him.
  • Why?
  • I’m afraid of what might happen.

Suddenly you have a more specific situation to work on–how to speak up effectively, and what to do if it doesn’t go well.

(Note: when your “why train” hit the feels instead of the thinks, you’re in the right place. More in this article, Why You Need Emotion at Work.)

Part 2: Where do you want to be?

Whenever we’re experiencing career questions or stress, we start thinking the answer to “where do you want to be?” is “anywhere but here.”

But again, let’s get really honest.

For most of us, “where” is likely NOT a location or specific company, but a state of mind, a way of feeling.

After traveling down the “why” path and getting honest about where you are, your “where you want to be” often is more like:

  • I want to feel more confident to speak up
  • I want to work for someone who respects what I do
  • I want to act with more courage at work

You’re narrowing down what you want in the future. That makes it significantly easier to create steps to get closer.

Which leads us to . . .

Part 3: What’s the simplest next step to get closer to where you want to be? 

At this point, you’re clear on where you are.

You have a picture of where you want to be.

Now, what do you DO?

Truth is, you might already have figured that out once you told yourself the truth about where you are and where you want to be.

But if not, here’s my favorite strategy to use:

  • Open a new document on your computer, or take out pen & paper.
  • At the top, write “Possible Steps to Get Closer to [Fill in your “Where” here]
  • Set a timer for four minutes.

  • Hit start and begin writing as fast as you can. The goal is quantity, not quality.
    • Don’t censor yourself by questioning whether or not the step is possible. For example, if “wish for a miracle” pops into your mind, write it down.
    • Don’t stop and think about what anyone else would think about that step. This is just a sandbox for you.
  • When the timer goes off, you can choose to move to the next step, or if you’ve still got juice, throw another two minutes at it. But that’s it–more than that and you begin to stray into overthinking zone.
  • Review each item on your list. If you can, read them out loud.
  • Circle (or highlight) the ones you could do right now, without any extra training or tools. For example, many times our simple next steps are scheduling a conversation, making a phone call, booking an appointment, etc.
  • Do that one thing.

Voila! You’ve taken an essential first step.

Don’t discount this as oversimplistic. Knowing we’ve made forward progress helps tell our brain we can continue, and breaks us from the suck of stuck.

Plus, don’t forget

Now, you’ve got your agenda, and tools to use within each segment.

When you’re ready to begin, don’t forget this one important thing.

Assign each of these sections a start and stop time, with room for breaks and/or meals, too.

Then, set an alarm for each segment, even if you have hours to invest.

Knowing the clock is ticking always makes you cut through the mental fog and work more efficiently. After all, it’s ticking on our life everyday–making time more visible helps us use it smarter.

Hey—want more help?

No matter what’s happening in your life at work, a 30-minute chat with me can help you get unstuck and move forward, fast. 

Just hit the button below, and pick a date and time that’s available. Answer a few short questions, and then I’ll call you at the time you picked. There’s nothing to prepare–just show up right where you are. If, after we talk, it sounds like one of my coaching programs or courses will help you going forward, I’ll share details after our call. There’s no pressure -my goal is to be helpful immediately.

Spots fill up fast, though, so schedule yours now and start getting the support you deserve.

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Read this next:

How to Plan Your Career Retreat (+ Downloadable Planner Inside)