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Personal Strategy Review: Highlights, Lessons Learned + Best Books, Podcasts and Other Resources

By January 3, 2017 No Comments

Earlier this year I wrote about society’s collective “Alice In Wonderland” problem.

Simply put, too many of the world’s most intelligent, driven and well-resourced men and women can’t answer three, critical questions:

  • Where am I, personally and professionally?
  • Where do I want to go?
  • How am I going to get there?

The secret, as I see it, to answering these questions with confidence is to create a habit of a regular “personal strategic review.”

Done well, this is a 60 minute process where you simply reflect on the past 90/180 days, asking a series of questions designed to help you better understand, and answer, these questions.

A few years ago I made a commitment to living a more “intentional” life; a life in which I feel both in control of, and confident, about my decisions made, and path forward. This strategic review process is essential to creating that outcome.

The structured and systematic process affords me clarity and security in a world full of opportunity and uncertainty. It also ensures that I truly learn from my mistakes and, just as important, spend more time appreciating my accomplishments, large and small.

In short, this is the most important work that I do all year.

For the first time, I wanted to share my review with you in hopes that you can both learn from my mistakes as well as use this as a starting point for your own personal review and reflection process.


1. What Went Well?

The most important book I read all year (more on “best books” later) was Deep Work by Cal Newport.

In a nutshell, Newport suggests that the surest path to long-term security and impact is to cultivate an ability to do deep, focused work. In other words, cutting out distraction and spending consistent time every day/week working hard on your most important work.

When I think of what “went well” this year, my ability to create space for, and perform, “deep” work stands out.

During these periods of focused work I made huge strides on my “Catalyst” Personal Strategic Planning approach. I was able to develop and refine a new, more efficient approach to “discovering” Personal Core Values and I was able to dramatically improve my personal approach to corporate strategic planning.

Implication: I must continue to invest in deep work and increase the total number of hours I commit to it. Action: I plan to measure, specifically, how many hours I am spending on deep work.

2. What Didn’t Go Well?

At the start of this year I had two ambitious, but achievable, goals — neither of which I made progress on:

1) To launch a new group coaching program: Personal Finance For Leaders (My hypothesis: too many otherwise smart men and women are making sub-optimal personal and professional decisions due to a lack of personal financial acumen. I had planned to create a short, bootcamp-style program to help these folks get their personal financial life in order).

2) Write a 40,000-word book: “Regret Free Life.” The book would capture my best ideas and approaches on how to make great personal and professional decisions and create a life of energy, engagement and impact.

Neither of these things happened.

Why? In short, two reasons…one “good,” one “bad.”

The “good”: My work on “Catalyst” was adopted by some incredible companies and supporting them required more time, energy and resources than I had expected.

That was a big deal. The increase in the number of Catalyst engagements made the program and process much better. Going forward, I expect that the Personal Finance For Leaders work will “live” within Catalyst as they are directly related.

The “bad”: I didn’t hold myself accountable.

Particularly when it came to the book, I would “think” a lot about it but only rarely sat down to work on it. I had made a very reasonable plan to write 200 words a day until the first draft was finished but, looking back, hit that target less than 30 times all year. If there is a silver lining in all of this, it’s that I know appreciate the need/importance of accountability more than ever (more on that in a second).

3. What Did I Learn?

I learned a ton this year. Here are a few of the most important takeaways:

  • Core valuesPersonal Core Values Matter: I never *really* understood what values are, how they work, and why they matter until this year. I have come to a much more sophisticated (and simple!) understanding of how our values affect our decision-making and how important it is to know your values, and act accordingly. Perhaps most importantly, I was able to clearly define my personal core values and guiding principles (see image, right).
  • Being A Dad Is Hard: I am 39 years old and I have been a father for just over 3 years. For roughly 35 years, I had a romanticized notion of what fatherhood was. Over the last 12 months, I have learned that “great” dads are so much more than friends or playmates. They are role models. They do what’s right, even when it’s hard. They are patient, even when they’re stressed. They don’t take sick days. They are always teaching, because our children are always watching and learning.
  • Physical Health Is The “Lead Domino”: When my wife and I launched our new group fitness studio, our mantra was “Healthy Together.” We wanted to leverage the power of community to help people create and sustain a consistent exercise habit. We had a hypothesis that, all things being equal, if you are physically healthy — all of the other “hard” stuff of life gets easier. Put another way, when you are physically well, it’s easier to be the kind of parent, spouse, colleague or leader that you want to be. Over the last nine months this hypothesis has been validated many times over.
  • Social Media Isn’t “The Root Of All Evil,” But It Doesn’t Add Much Value To My Life: If you follow me on Facebook or Instagram you’ll see that I post a lot of articles on leadership/decision-making and cute pictures of my kids. I enjoy doing that but the value of this investment in social media has very little lasting ROI in my opinion. This year I worked hard to avoid “mindless” surfing on social media by removing the apps from my phone and using tools such as Freedom, Facebook Newsfeed Eradicator and MeetEdgar to reduce both the need, and temptation, to be on these platforms. That said, I still find myself using the medium to distract myself and/or avoid loneliness and rarely (if ever) do I emerge from one of these social medium “black holes” feeling more energized, excited, and ready to do the hard work that I have to do.
  • Our Family Life Deserves The Same Level Of Rigor As Our Professional Life: Earlier this year Sarah and I began to think of ourselves as co-CEOs of “Sands Co.” and a bunch of good stuff started to happen. First and foremost, we were able to quickly get aligned on our top priorities as a family, as a couple, and as individuals. That alignment then translated into easier conversations about everything from money, to daycare, to in-laws. The process involved a few hours of candid conversation during which we discussed and shared our personal core values, our goals as a family, and our “operating model” — i.e. how we can best work together, leveraging our strengths and values, to create best possible outcomes.

4. When Did I Let Fear Hold Me Back?

I believe that fear is root cause of every poor decision that I make.

Accordingly, I find it important to recognize where fear has held me back so that I give myself the opportunity to intentionally choose a different emotion when faced with similar choices in the future. Here are a few examples from this past year:

  • Writing. Producing these articles is one of the hardest things that I do. I enjoy writing; in fact, it is through writing that I really come to understand what I think/feel. Despite that, I tend to worry too much about whether people will “like” the article and/or how well it stacks up to the quality of the authors and bloggers I most respect and admire. I am most successful at combatting this fear when I remind myself that, as long as one person reads something that allows them to move their life forward, then the effort has been worthwhile.
  • Hiring For Sands Leadership. I have had some wonderful opportunities to collaborate with other thought leaders, coaches and entrepreneurs this year. Through these collaborations I have experienced, first hand, how much more is possible when working with other talented, driven and dedicated professionals toward a common goal. That said, I have yet to hire my first team member. Among the associated fears: 1) That despite all of my knowledge about leading/managing I am going to stink at it, 2) I won’t be able to afford the quality of team member I hope to hire and 3) I am going to hire the wrong person — setting myself back both strategically and financially.
  • Investing In New Relationships. Ironically, I have become so obsessed with doing “deep” work that I think that I have under-invested in something equally valuable: building high-quality, value-add personal and professional relationships. This year I plan to manage that fear by being more thoughtful and intentional about this process (e.g. fewer one-off “coffee” conversations and more group dinner parties and other experience-based get togethers, ideally including Sarah).

5. Am I More, Or Less, Financially Secure?

As mentioned above, I have found that a lack of personal financial awareness/acumen is the root cause of too many sub-optimal personal and professional decisions.

One of the solutions I have found to be helpful in managing money-related anxiety: tracking my five “Regret-Free” financial metrics.

  • Cost Of Living: How much does our life cost, on a monthly basis?
  • Cash Flow: How much more (or less) are we earning, compared to spending?
  • Return on Investments: How well are our investments performing?
  • Savings Rate: How much are we saving, each month?
  • Charitable Giving: How much are we giving away?

Because I know these numbers, I can quickly determine if “Sands Co.” is making decisions that are making us more, or less, “financially free.”

This year we increased our financial security in a few important ways.

First, we were able to maintain a stable cost of living.

I often remind my clients that “the lower your cost of living, the more choice and control you have over where you spend your time.” I am trying hard to practice what I preach.

All in, our monthly expenses are approximately $6,800. It’s not like we are living on Ramen noodles, but we have done a good job of not buying stuff we don’t need and cutting the fat, where possible.

One of our best ideas of the year was to hire a bookkeeper to help us organize our personal finances in a way that brought greater transparency and clarity to our personal financial situation. In short, we made the decision (and investment) to bring the same level of rigor to our family finances that we bring to our business finances.

Second, in order to cut costs, plus create greater visibility into what our investments are doing, we consolidated our securities investments (stocks, bonds, ETFs, etc) with Betterment.

Betterment is a robo-advisor that allows us to invest our money in an incredibly low-cost and efficient way in a manner consistent with what I consider to be “best practice.” Like most portfolios, ours went up in 2016, but not by much — Betterment tells us that we had a “simple” return of 3.7% driven mostly by dividends.

Third, we intentionally re-adjusted our charitable giving allocation to better reflect our values.

Halfway through the year, Sarah and I sat down to reflect on how our charitable giving aligned (or not) with our values.

We believe that “to whom much is given, much is expected” (core value: accountability) so we were a bit embarrassed when we realized that our charitable contributions were just under 2% of our income. We quickly bumped that allocation up to 5% and set about finding worthy charities in whom to invest.

In addition, we committed to our first ever “major” ($60,000) gift. Writing the first $12,000 check (it’s a five-year commitment) filled us with both anxiety and a sense of abundance. Now, many weeks after delivering it, the anxiety is gone but the sense of abundance (and gratitude) remains.

Note: if you are interested in charitable giving strategy, don’t miss this episode of Malcolm Gladwell’s excellent podcast “Revisionist History.”


Finally, I wanted to share a short list of some of my favorite books, podcasts and other things from this year. You can keep track of my running list on my Resources page.


I read, or listened to, 36 books this year including, for the first time, a number of “fun” fiction books. (A special thanks to Sarah for helping me realize that I prefer ending my day with a fun book over a Netflix binge-session).

My five favorite non-fiction: 

My five favorite “fun” fiction:


Other Favorite Things

  • Beats PowerBeats 2 Wireless Headphones – great for listening to books and podcasts, as well as talking on the phone. Sweat-proof and stable, too – great for working out.
  • Lululemon Surge Warm 1/2 Zip – the most functional and useful piece of clothing I own. Wear it nearly every day in the fall/winter.
  • The Week Magazine – I subscribe to the print magazine; a collection of a week’s worth of news pulled from a wide-variety of sources, both domestic and international. Allows me to stay off time-sucking sites like,, etc.
  • Brain.FmMusic to help you focus, meditate and relax
  • Canva.comThoughtful and intuitive graphic design app (an idiot’s Photoshop or Illustrator). Makes the creation of images, illustrations, blog graphics and the like incredibly easy.


I hope that you’ve found this reflection useful. My hope is that you will be able to employ a similar process/approach to review + reflection in your life.

There are no guarantees that the year ahead will be better than the last, but I feel strongly that through intentional and regular reflection and planning that we can dramatically increase the probability that it is.

Good luck, and thank you for your continued support, friendship and collaboration.

Ben Sands

Author Ben Sands

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