Five Strategy Questions to Ask Today


Do You Have A Strategy To Create A Life You Love? If Not, Read This…

By July 31, 2012 3 Comments
By Ben Sands – For additional insights, tools, and leadership resources, click here

Last week, a new client shared this frustration with me:

“I feel like I am not living ‘intentionally.’ Life is happening to me as opposed to happening because of me. I’ve got to do something about it.”

The week before another client expressed a similar sentiment.

She said: “I want to start being pro-active in my life, as opposed to be re-active. Too often I let external circumstances dictate what I do, how I act, how I feel…”  

Does this sound familiar to you?


I am not surprised….we all have a major strategy problem.


Before starting Regret Free Life I spent many years in traditional management consulting where I worked with companies to help them adjust or enhance their business strategy going forward.

Simply put, a “strategy” is a best guess at what specific actions need to be taken, in what order, to most quickly and cost-effectively achieve the outcome wished for.

I say that it’s a “best guess” because every strategy is built upon assumptions – a set of predictions, grounded in fact and previous experience, about how things will turn out.

Whether you know it or not, you have a life strategy.

Your life strategy is the series of steps that you’ve taken (since high school or before) to create the life you are living today.

This strategy has manifested in every decision you’ve made – about what to do for work, where to live, how to spend free time, etc.


Take a second to reflect on your life plan to-date – the series of decisions that you have made since graduating college.

What were the assumptions you had about how life would turn out in the subsequent 3, 5, 10, 15 years?

How many of those assumptions proved true?

Now consider your plan going forward.  What assumptions are you making about what will happen going forward?  How certain are you that those assumptions will prove true?  Most importantly, what is the measure of a successful plan?  What are you REALLY trying to accomplish?

If you struggle with any of these questions, join the club.

If you’re scratching your head trying to figure out what assumptions you are making, it’s  OK.

If you’re feeling just slightly deflated because YOU DON’T ACTUALLY KNOW how you will know if your strategy has been successful or not, don’t beat yourself up.


The foundation of smart life plan is two things:

1. Clarity.

Understanding what you are trying to do…the REAL goals – the targets that will endure over time.

Note: these are typically feelings, not things.

Salary, title, home(s), car(s)…these are moving targets.  Moving because, when you get them (which you will!) you are going to want something else – something more impressive, more expensive, more sexy, more massive.  We need a target that won’t move – a goal that can endure, over time, regardless of what life throws at us.  I’ll show you how to do this in a second.

2. Execution.

In his book, How Will You Measure Your Life (one of my favorites), Harvard Business School professor – and strategy guru – Clayton Christensen says, “a strategy becomes a plan only after you’ve started to allocate resources.”

In our case, the resources which we have to allocate are three-fold: time, energy, money.  How we allocate these resources is how we ultimately execute our plan.

For those who want to start living intentionally, making conscious choices, being pro-active as opposed to re-active…it starts by first choosing what we want, then executing against it.


Most people call me up asking “what should I do?” and I inevitably ask them in reply “well, what do you want?”

On the other end of the line: silence.

Such a simple question…What do I want?

As it turns out, this may be one of the most challenging questions for any smart 20 or 30 or 40-something to answer!

Sure, if you asked someone today (and I would suggest that you do so) they would likely have an answer: e.g. “a great job!”; “a beautiful and loving wife”; “a Ferrari!;” “a ski house in Aspen,” among many, many others.

The problem with these answers however, is that they are subject to change – they are “moving targets.”

What we really want are hard goals – things that will be important, will matter to us, regardless of our material possessions or stage in our life.

Ultimately, what we really want are feelings.

Some of you might be thinking: “Feelings?  I am working my ass off for a feeling?  Come on…”

And I get it.

Truth is, feelings are both hard to measure and hard to hold up as a symbol of achievement.  Of course you want to be happy, right?  But would you jump off the career “fast track” for it?

Probably not.

Because in your mind happiness and achievement go hand-in-hand.

And achievement takes time – or at least that’s what we’ve been told. So many of us have grown used to forgoing near-term and fleeting positive feelings in order to achieve “long term” goals.

“Delayed gratification” is a strategy that so many “high-potentials” (like you and me) espouse.  The problem with this strategy however, is that it never becomes clear when we should stop delaying the gratification – and when we should start enjoying it.

When will you have what we want? When will you be happy enough?

Don’t get caught in this trap.

Define first the feelings you hope to maximize in your life – love, security, significance, growth…and start creating these feelings in your life today.

No more putting it  off.

How successful have you been at crafting your life strategy to-date? What has helped you? What has held you back?

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Ben Sands

Author Ben Sands

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