Since we live in a goal-obsessed society, I bet you can rattle off several things you’re hoping to do, be, or achieve right now.  I know I can. But how many of you are stuck on the action part?

We all get stuck from time-to-time. Sometimes we’re stuck for a week or a month, and other times we get stuck for years.  I see it with clients when they’re trying to take a challenging action that is in their best financial interest. I see it very often with career moves like the desire to get away from a soul crushing job/boss or deciding to start a business.  

We tend to keep ourselves in tough situations that prevent us from moving forward simply because we don’t know how to move forward. There may also be fear.  If you’re like me you may be scared to admit you want something because you have no idea how to accomplish it. When we’re scared to say we have a goal we’re working on, it becomes even harder to take steps to achieve it.  

I have a goal like this. I’ve been saying I want to write a book for at least two years. Every year at the beginning of the year I write it down on my list of goals. And every year I’ve done almost zero things to make it happen.  While I’ve had it on my list for two years, I had it on my mental list for several years before that. I was just too scared to actually put it on my list because I have a tendency to not even try something if I think failure is possible.  As of January of this year, my goals was there, memorialized on paper. But I had no deadline, and no path to starting or completing it. Few people even knew about my goal. If you had pressed me, I would’ve said, “Oh, I don’t know….it’s something I’ll tackle in a few years.” 

Well, I’ve had a big change of heart.  I am writing a book…this year! And I’m going to have an initial manuscript completed this summer.  There will be more announcements to come on that, but in the meantime:

How did I go from saying it was something I was going to do in the far-off distance to taking action?   I had some help. And what I found out was that I had the answers to the way forward all along.  I just needed the time, space and prompting to help me through it.   

Here’s what it took:

A friend walked me through these 6 powerful questions we learned at a recent training at the Kinder Institute for Life Planning.  Now I have a crystal clear path forward and I’m taking action.  When I encounter bumps or missteps or get discouraged I can start asking myself these questions again to get me right.  

As I share this knowledge, I will caveat that while these questions are powerful, they can be even more powerful if someone else is leading you through them.  That way it’s harder to weasel out of answering them properly or claiming one of them doesn’t apply (believe me they ALL apply). It’s also really motivating to have someone really listening to you and witnessing you think about solutions and action steps.   So — feel free to try answering them on your own, but with the caveat that you may want to plan on having someone prompt you later anyway.  

So first take a moment.  Envision your goal, write it down, and try to feel what accomplishing this goal would mean for you.   Got it? Now ask yourself:


1) What could possibly get in the way?

It can seem counterintuitive to spend time thinking about the obstacles that can get in the way of us achieving our goals, but that’s exactly what our brain craves – knowledge of what can get in the way and something to focus on — action steps — for addressing those obstacles.

A typical answer might be “me,” or “I don’t know how.” Or maybe you’ve thought about it and you already can think of 8 reasons why you can’t or won’t do this. Do you feel like you don’t have enough time to achieve it? Are you fearful of moving forward? Is it a financial concern? Are you missing knowledge or a credential?    Capture those obstacles without any judgement. Take each potential roadblock separately and write them down on separately lines. Once you have each roadblock written, start with the first on your list and ask yourself:

2) What can you do about that?

If your answer to the first question was “I don’t know,” perhaps asking yourself what you can do to get more clarity could lead to some insight.  If your answer to the first question was that you’re getting in your own way, asking yourself “what can I do about that?” might feel empowering. If you’re the kind of person that can see the roadblocks clearly — take the first roadblock and brainstorm: what can you do about that?   If you get stuck on answering, ask yourself “what could you do to get unstuck?”  

Some typical answers might be — I can ask for help, I can talk to someone, I can do some research, I can take a walk, I can get some space, I can create an affirmation, I can brainstorm, I can sign up for a class, etc.

3) How are you going to do something about that?

Now here’s where the exercise starts to take a turn.   Asking yourself what you can do is only slightly different than asking how, but it’s the “how” that is extremely powerful.  It puts you in a position of taking action. What comes to mind first?  

Keep re-asking, “how will you do that?” — drilling down on the how until you feel like you’ve come to a completion point.  Maybe you’re listing the steps you need to take, maybe you’re discovering new roadblocks. Maybe you’re finding this is easier than you thought?   Asking yourself “how” is very powerful.  

If you’re like me you might even feel excited because the action steps feel doable and attainable.  Doable and attainable calms a lot of my fears and gets me motivated. What about you?  

Once you feel like you’ve gotten all you need out of the how question, then ask yourself:

4) When are you going to do it?

Now we’re getting somewhere.  For each of the things you listed in your “How,” put a date on it.  Try to make these bite-sized and reasonable. Yet, challenge yourself.  If you find yourself setting a date way off in the future, it probably means you aren’t very serious or that you haven’t broken down some of the “how” into small enough steps.   

A prompt you might use is, “When in the next two weeks (or month) will you do that?”  Or “What can I do in the next week to start on that?”

An actual plan is starting to emerge.  How is this feeling? Keep going with that energy and then ask yourself:

5) Who can help you with this?  

We all need help.  Sometimes we need help on taking action steps because we need advice, guidance, or knowledge.  Sometimes we need help from someone to hold us accountable so that we do what we say we’re going to do.  Studies show that people who tell their new year’s resolutions to someone are more likely to achieve them.  So who’s going to be the one to help you out with this? Once you’ve got the person in mind, briefly write down how and when you’re going to ask them for help  (reverting back to the previous two questions briefly), just to set expectations for yourself.  

Then, to make it all stick, ask yourself: 

6) How would it feel to take action on this?

Well if you’ve made it this far, hopefully these questions have created some energy, a sense of excitement or anticipation.  You have action steps, an action timeline, and help/accountability. How does it feel to have a plan of action? How would it feel to achieve this goal you’ve been feeling stuck on?   What would it mean to you to be able to accomplish this?

Is it surprising you were able to accomplish all that with 6 simple questions?   I know I was.  

Now maybe going through this process once was all you needed. But for some of us, we might have had several items on the “what could get in the way?” list.  You can then start with the second item and run through the questions again until you’ve addressed all the roadblocks. In fact, anytime you run into a roadblock or a feeling like you don’t know how to move forward — starting asking yourself the questions again:  What – How – When – Who — How would that feel?

If you’re interested in reading more on the science behind why this works – it is, of course, about training our brains.  The Kinder Institute has done a tremendous amount of work developing this system to help consumers achieve their ideal life.  There’s another book called “Rethinking Positive Thinking” by Gabriele Oettingen.  The author has published nearly two dozen research papers on human motivation and why envisioning what can get in the way has the ability to spur us into action.  And he pioneered a similar method he calls WOOP, which stands for What’s your Wish? What’s the best Outcome? What’s your main inner Obstacle? What’s your Plan?    “Indistractable,” by Nir Eyal is another great book that follows these concepts and includes many other tips for maintaining traction and getting results.   

While I find the science fascinating, I’m simply stunned at how different I feel about writing my book and how motivated I am to do it just by having someone ask me these 6 powerful questions.  

For reflection: When you try this process did it spur you to take action where you were unable to before? Did you find that reviewing this with another person was more effective than journaling on your own?

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