Field Guide to Transition #203

Four Questions to Help You Through the Messy Middle…


So much of what I’m observing these days in the personal development literature and thinking has to do with big goals and small steps.  Any big project is daunting, and so much of the work is hard, messy and in the middle – far from the beginning and end, and easy to lose sight of the dream, of what is possible.

When I was in the depths of my own transition, building out my career goals and looking for work, a mentor of mine asked me these questions in our coaching meeting on 8-19-13:

  1. What would be the ideal outcome of the transition process you are in?
  2. What is a small step you could be taking right now towards that outcome?
  3. In what ways do you create obstacles to that outcome?
  4. What would you like most out of your time with me today?

There were many days during my own messy middle that I thought I was going to lose my mind with frustration.  I understood exactly what Joan Didion meant when she described “the shallowness of sanity” in her book The Year of Magical Thinking.  Hundreds of resumes sent out to the abyss.  Questionable financial runway.  Marital discord.  Extreme distraction – so many things to do and not enough time to do them.  A bottomless well of doubt and a feeling that this may never change.  No real feeling of accomplishment.  Anxiety as a constant companion.  Never a sense of peace.  Putting on the game face and networking – perhaps the most emotionally difficult part of the whole equation.

I was working on the riddle of how to take my unique recipe of experience, skills, thinking, and strengths to find my career sweet spot, but also to create a vision of what I wanted my life to be, as an ecosystem, as a whole –  at all levels.  It started with questioning the next steps in my career and ended in a complete interior renovation.


The coach who asked me these questions made me very uncomfortable.  His directness unsettled me.  I didn’t enjoy our time together.  But to his credit, he broke through the BS I threw in avoiding some hard truths.  He was willing to risk being liked for being effective, and his lessons have stayed with me.

These four questions together are very powerful.  Question one invites big picture thinking.  It asks that you define a goal.  Here’s what I propose to others when dreaming up goals:  When considering the ideal outcome, don’t limit yourself to your current situation.  Forget about money, time, and dream as big as you can.  As it turns out, we almost never dream big enough – we consistently impose limitations on what we think we can achieve or do.  Action point:  keep notes of what you think you want to do.  Get over yourself if you “don’t like to journal.”  Call it something else, but just do it.  It is a tool that can help you wade through the choices, and over time it will help you see trends in YOUR thinking, YOUR aspirations, and will thin the herd of ideas that stop us in our tracks from deciding and taking action.

Question two asks that you define one small step to take towards that goal.  It’s easy to say that “Rome wasn’t built in a day,” but during a transition or when building something new, it is so very hard to keep perspective when the finish line seems so far away.  Placing these two questions together mitigates this.  If you are at the beginning of a transition, the small steps you take may be the ones in which you test out your ideas and explore your interests.  For my career overhaul – I started with research – by taking personality assessments and researching professions.  I had defined my goal but was looking for the bridges connecting my interests with my experience to create something that would hold my attention for the second half of my career and would provide a satisfactory livelihood.

If you are further down the road with your endeavor, staying focused on the larger goal but outlining the next step is critical, and having faith in your process is essential.

Question 3:  In what way do you create obstacles to that outcome?  Liz Gilbert, on a podcast with Lewis Howes talked about not having enough time for writing, yet finding herself in front of the TV in the evenings.  Her friend pointed out to her that how you spend that hour –  that is a choice.  We often hear people talk about how they don’t have the money to travel, yet they regularly buy expensive coffeehouse coffees.  There’s nothing wrong with either choice, but we can’t really say we “don’t have the time” or “don’t have the money,” when in fact, we make daily choices that prevent pursuit of our goals.

We all know this and may even be aware of it every time we buy the coffee or watch the show or do whatever it is that chips away at the larger goal we dream of achieving.  Every time we run this script, a few grains of our self-confidence erode, and we begin to create a believable, but untrue story.   I, too have an exceptional stable of excuses to support the story of “not having enough time to write.”  My script centers around my schedule which includes:  seven hours of sleep, 90 minutes of daily commute time, eight to ten hours of work, time to parent my teen, some semblance of showing up as a wife, nourishment, exercise and personal care.  There truly isn’t that much time left, but if I am serious about writing, I will find the space in my day to attend to it, and not allow my schedule to be an obstacle.   And 30 minutes a day of writing, while not a lot, adds up to 210 minutes per week, or 3.5 hours.  Over the course of a year, that is 182 hours of writing time!

Question 4:  What do you want out of your time (with me) today?   This is effective because it requires two things:  focused attention and choice.  The time for focused attention is finite and setting a time limit primes your mind to hustle.  Deep work and progress can come from even just 25 minutes of this type of attention.

During my job search, I was introduced to the idea of accountability partnering by my friend, Karl.  He provides leadership development services to organizations and individuals, and we worked together over the course of four weeks.  We defined a goal and a few next steps that supported the goal.  We would then check in at regularly scheduled intervals to discuss progress.  One item on my list consistently wasn’t getting done, and after four weeks it became clear I had other priorities.  Paying attention to this and having him hold me accountable allowed evaluation and a decision:  on or off the list?  The question then becomes, is this an avoidance tactic, or is this task essential to reach the goal?  In this case, not essential.  I never had to consider it again, and making a conscious choice left my mind free to consider different options.


This is a process, and it can be painful, especially in the middle.  The payoff comes from consideration, time and effort – there is no shortcut.  In those moments of doubt, of pulling your hair out, of wanting to chuck the whole thing, hopefully there is a part of your brain that remembers that the big goal, the dream, this hard work…will end, and will be worth it.

Some resources to get you through:


Photo by Samuel Zeller on Unsplash


Hi all! I love to write on the things in life that bring joy and encourage clarity in our lives. 

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