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The curse of “keeping your options open” and how to break it

Growing up, it's common advice to "keep our options" open, but in adult life, doing this actually paralyses us.

Over the years, I’ve had many conversations with team members, friends, co-workers and even bosses about big decisions in life. Usually, it is triggered by a problem or situation they feel trapped in.

If there is one instinct that consistently holds people back from finding a way out, it is the instinct to keep all their options open. For example, I’ve spoken to many people who are dissatisfied with their jobs. When we brainstorm, lots of different options come up. Should I try the five possible interventions which could improve my current job, push harder on my search for a new job, or find something I enjoy outside of work to boost my sense of well-being?

Others are thinking about a very specific problem at work, or in their family life.

What is common is that people are often very clear about their options, but if I check in with them a few months later, they have barely made any progress in moving ahead with one of the options. Many are still waiting for the circumstance to change.

Why do people get stuck when they are keeping their options open?

Why do people get stuck like this? I believe that it is merely a symptom of trying to keep all their options open. Here are some of the dynamics at work:

First, because time is a limited resource, it is impossible to pursue all the options, at the same time, with all your heart. You will never know if you did not get the result because you did not try hard enough, or whether it was an ineffective intervention. The end result: feeling burned out, but without any more clarity on which option you should take.

Second, when we are obsessed with keeping our options open, we tend towards risk aversion: avoiding actions which may entail trade-offs in any of the other options. Real examples that I have heard: if I push harder on my job search and invest less time in my current job, will my boss put in a negative word to my future employer? If I dedicate a few months to try out an intervention which might make my current job more meaningful (but might also fail), will I miss the window to get employed in this growing sector? If I get a new job, will that mean working twice as hard and giving up on other life priorities such as getting married and having a child?

In our minds, we create a web of options, consequences, causes and effects, and get tangled up within it because we are trying to do the impossible: find a course of action which does not create the possibility of negative trade-offs for our other options. As George Leonard writes in his book “Mastery”: “how can any option, any one goal, match up to the possibilities contained in all the others?”

Suddenly, all the options start to seem incredibly risky – so risky that perhaps we should not act. As a result, keeping our options open is often a tiring mental exercise which yields very little new insight or momentum.

Good news: The horizon of possibilities is wider than you think

When we are paralysed in trying to keep our options open, we miss out on whole horizons of possibilities. The fact is: each time we take a step forward, new possibilities are created because we, the people around us, and circumstances change in ways we cannot anticipate.

For example, committing to having ten conversations with potential new employers in the next two months may lead to a new job opportunity. It could also generate new ideas for how you want to shape your current job to make it more meaningful. You may meet someone to partner with on a meaningful side-project. Your boss may finally realize how much you were doing when you stopped picking up the slack for others by working in the evenings. Personally, you may get a clearer sense of your life priorities as you talk to people outside your traditional circles.

When you commit to a step forward, you may trade-off something from other options, but you also generate tremendous new insights and possibilities that could not have been anticipated in your original web, simply because you cannot predict the future.

An alternative: time-bounded experiments

What’s an alternative approach to “keeping all your options open”?

Let’s say you are faced with a problem, and you’ve done your homework by laying out the options and trade-offs. The next step is to make a time-bounded commitment to one option, and quickly move ahead to execute on this commitment. Using the same example above, you can set aside two months to work on a set of interventions that could improve your current job situation, or commit to ten conversations with new companies. I suggest picking one at a time and if you are a person who tends towards “doing it all”, also make a list of what you will NOT do during this time-bounded commitment.

Once a time-bounded commitment is finished, evaluate it with someone you trust – a mentor, coach, or peer. Is there a compelling next step which draws you in? If so, take it. If not, you will now have a better sense of what resonates with you, and a slate of options that are either a combination and extension of your initial slate, or completely new altogether. Repeat the process of making a time-bound commitment.

The beauty of this process is that within two to three cycles, people typically land on something that does not feel like “just one of the options”, but the path they are ready to commit to for a longer time. Even better, they feel energized by taking action, and have now built a new repertoire of experiences and networks. This is in contrast to the energy-sucking paralysis of trying to “keep all your options open”.

If this sounds process familiar, it is simply the methodology which many innovators take: low-cost, time-bounded prototyping; except applied to your life.

*Rinse and Repeat

As with most "good advice", this is easier said than done. Two things are essential to keep yourself on track:

  • Stick to your time-bound – if you are a person who likes to keep your options open, you will be tempted to revert to trying to “do it all”, resulting in exhaustion and confusion. I have a friend who put a calendar up on her desk, and each time she felt insecure about “not doing enough”, she referred to the date when her time-bounded experiment would end. This gave her license to rest and recharge (never underestimate the importance of rest to a sense of perspective when attempting to make a transition.)

  • Stave off the urge to evaluate the effectiveness of your actions (what you have gained and lost) until the commitment is complete. If you are constantly in “evaluation” rather than “experimentation” mode, which many results-oriented people are, you will miss out on important insights and possibilities which open up as you take steps forward. Stay open by suspending evaluation to a committed date.

To this end, engaging a coach for time-bounded period can be a good idea. Coaches are helpful in at least two respects.

  • First, when we are evaluating our options at the start line, we are inherently biased in our assessments of what is possible and impossible. A skilled coach will help you see possibilities you would not have seen on your own. More importantly, he/she will help you break down seemingly insurmountable tasks into steps you are comfortable to take. You will feel bolder and more supported in taking important steps.

  • Second, coaches help with accountability. Many of us, left to our own devices, tend to break our commitments to ourselves. It is useful to have built-in accountability for the period you are doing this important work of experimenting and evaluating.

Rounding up

Feeling dissatisfied, facing complex problems and feeling like there is no clear path forward: these are common parts of our professional and personal lives which lock us in a combination of fear and inaction.

George Leonard’s “Mastery” reads: “Ultimately, liberation comes through the acceptance of limits. You can’t do everything, but you can do one thing, and then another and another.” When you feel stuck, make time-bounded commitments and put your whole heart into them. Create accountability structures so that you commit to the process – a coach is one way. You will find that the process changes you, opens new possibilities, and helps you prototype your way into something that does not feel like “an option with trade-offs”, but the right path for you at this moment.

  • What are areas of your life where you are dissatisfied, but feel that you have no good options?

  • What are the time-bounded experiments that you can commit to?

  • Who can you approach to walk through this process with you?

An Offer

If you'd like to get started, get in touch for two free 30-minute sessions. My practice focuses on career transitions: whether you'd like to start something new, become a better manager, make your current role more manageable or meaningful, start a side-gig or improve your presence as a leader, coaching can help you take concrete steps towards this.

I coach over video (Skype/Zoom/Facetime), so it doesn't matter where you are in the world. Drop me an email at to let me know 1) where you're from and 2) what issue you'd like to work on.


#coaching #options #leadership #jobtransitions #executives


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