Earlier this month, my grandmother turned 88 which, as a Chinese friend will tell you, is a far more auspicious number than 44. That said, 44 isn’t all that bad.

44 is further than I ever considered in my teens, 20s and 30s – it’s a bit of a shock to arrive, which lets me know that my 50s are going to be here before long. With that in mind, I’ve started reaching out to my smart pals, already in their 50s, to hear their advice. I’ll share their best stuff as I gather it.

At the end of 2011, I realized that it would be possible for me to spend another 20 years living in my own personal Groundhog Day – winning agegroup athletic titles; working at my coaching business; and going on extremely pleasant vacations with my wife.

My blog post on A Life’s Work shared the questions that I asked myself across the year and I’ve been brainstorming ideas for the next phase of my life. I’m fortunate to have world class Universities in Boulder and have been considering taking advantage of those communities.

What follows is an end of year braindump. These articles are my historical record to see how I do with forecasting. 

Health – I feel better than when I was 39/40 and seeking to hang on to elite level fitness. I can remember being sore, tired and exhausted most of those years. The biggest surprise physically is being happy with a level of exercise that’s half of what I previously considered “maintenance.” Many of my peers still continue to “go big” – if they are reading then consider what you might do if your desire for physical expression moderates. You’re going to have a lot of time – unless you replace sport with children!

Family – after my divorce (early 30s), I was openly hostile to the concept of marriage and spent five years completely self-absorbed. I could say that I worked on my suitability to be a spouse but I’m not sure. Either way, I’m glad I gave marriage another chance. My wife and kids have transformed my life.

Something that I failed to anticipate, but heard indirectly from my friends, was how much I would be willing to change for my family. Parenting is filled with frequent moments of misery but so was elite sport! My athletic life was completely focused on convincing myself that doing-what-it-takes was more satisfying than short-term gratification. Great prep for fatherhood.

Business – Four years after the Great Recession of 2008/2009, I’m bothered by a persistent lack of ethics in peers, sport and finance. However, I have the education of my kids to fall back on and human drama provides motivation to remain vigilant with myself.

Finance – I completely missed how low interest rates would go. I think about the impact of a big burst of inflation but wonder if we will follow the post-bubble experience of Japan. We bought a house in December and took out a mortgage (3.25% 30-year fixed) to provide hedging for a burst of inflation. More on that in January. 

Education – Last week, I completed the draft of my next book. I’ll publish on Monday and you can download from this site. In reviewing the book (largely written in November 2011), I realized how much I’ve learned in the last year: mountain biking, family management, babies & toddlers, and international law. Even in my 40s, I can improve my human capital.

Self vs Family – there’s been a shift from optimizing for myself to optimizing for my family. If I had to project into my 60s then I expect my circle will continue expand beyond my relatives. I’d like to improve my participation in community as that’s a practical way to contribute to my kids.

Physical – my calf’s been jacked for a few months, my back is often tight, my eyesight is slowly fading but I can still do neat stuff in nature. A key mistake in 2012 was stopping running. 20 minutes every other day would have saved me a lot of hassle.

An important friend, Henry Simon, passed in 2011 and lived by the motto – Never Stop. It’s been 20 months since Henry died. Wow, that went by quick.

Future – I’ve learned a lot from watching older generations and asking them for advice. Key lessons for 2012:

• live near your kids
• give kids space, let them fail and insulate yourself from their failures
• to keep relationships strong, support the goals of others
• maintain independence as long as you can
• plan end of life care & legals far earlier than you think you’ll need

My marriage brings me satisfaction every single day. Three things that Monica brings me: kindness, a shared sense of humor and a desire to be a better man.

I try to live the life that I want for my children.

When my kids are lit up in the house, I have trouble hearing – thinking is impossible.

Recently, I presented ideas on how to manage a small consulting practice – the talk was about the ‘business of coaching’ and it centered on tips for managing one’s self. A key concept from the talk was to “choose one good idea and do it on Monday.” While I hope the audience was able to find something useful in the talk, I bet that the implementation rate was less than 10%. 

In my life, when I want to think strategically, I remove everything. In my 30s, my job required extensive travel so air travel was my chance to pause, and think. With kids, and a reduced travel schedule, I have to be strict with myself to create unstructured time.

In our marriage, we schedule couple’s retreats to give ourselves time to pause and think about the family’s direction. In my personal life, my cycling (alone, relaxed pace, no music, no phone) gives me blocks of undisturbed time. In Colorado, I ride low-traffic rural routes so I don’t need to be alert to traffic all the time.

To create the space to think in 2012, I did the following:

• Reduced my consulting workload by 80%
• Hired the equivalent of two full-time domestic employees
• Halved the time I spent training
• Doubled the time my daughter spent at school

This enabled me to see the areas of greatest value-addition for my family:

• Quadruple the time I spent with my kids
• Help maintain my wife’s sanity
• Write 100 articles – writing is the only way we can live beyond our deaths
• Triple my days spent visiting with key family

The above are big wins for my family, but fall outside of typical Boulder success metrics:

• family finances
• personal beauty
• athletic glory
• consumption tweeted or posted to Facebook

I’ve been trained to make money and seek consumption – those habits are reinforced by everything around me. The only place I’m safe is riding my bike in the forest and, frankly, I’d like to upgrade my bike!

In 2008, we changed because I lost my job. This time, the family changed before a crisis arrived. Thinking back a year, I remember my wife commenting that we should wait until we “had” to move (somewhere between 5 years and never).

I had a hunch that the changes would take the family to a better place.

Time will tell.

Question from a reader:

Why do we tend to crave/desire/pursue a path that doesn’t necessarily makes us happy? How come the external success (money, speed- race results, etc.) we work so hard for (both mentally and physically) does not lead to us being happier? Why does that disconnect which you wrote about it exist? How come external success is an illusion?

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I’m going to share some insights but much better would be to read Thinking, Fast and Slow as well as Seeking Wisdom. It takes effort (that most will never make!) to understand those books. The knowledge you gain will serve you, and your family, very well. Applying the knowledge in the books has saved my family time, money and suffering.

To kick off, not everyone makes poor decisions – I make poor decisions in some areas and excellent decisions in other areas. So consider the specific area where you’d like to improve. The areas where I make poor decisions (trusting too much, character) have been the same for many years. Knowing my blind spots, I make those decisions more slowly and take advice from my wife (much stronger in that area than me).

I accept the fact that my family is going to make mistakes – what we want to do is share the knowledge from our mistakes, write it down, and remind ourselves of the mistakes in our family’s history. I also want to make sure that we evaluate decisions based on the information we had when we made the decision. Written records such as file notes, investment summaries, budgets and strategic plans are essential to learn from decisions and evaluate the quality of those choices.

You mention happiness – my most important technique is to write down the characteristics of my “good days.” The simplicity of these days amazed me – because they were so simple, nothing stood out and nothing was remembered! The pleasure of quiet serenity disappears into the background stress of a busy life. 

Because I know that the media doesn’t understand what makes me happy, I do my best to limit media sources. If you look deeply at the source of the goals that leave you most disatisfied then you’ll often find a root in our popular culture, reflected in all sources of media (most toxic are popular culture, anonymous forums and tabloid journalism – we must ditch these when self-esteem is an issue).

The happiest weeks of my life are when I disconnect and exercise with my wife in nature. I share this observation because it is the purest form of my athletic motivation and I don’t need to win, or even attend races, to achieve this goal! A big motivator for my current restructuring is arriving at a point where I can greatly reduce connectivity. So far, I’ve managed to break free from Facebook and greatly reduce email time – thousands of (serene) hours will flow into my life from these two changes.

Think deeply about endurance sports and you may see that it is the time alone, and the exercise, that drives the psychic reward. It’s not the achievement. 

With athletic goals, I’ve released myself from the expectation that ANY goal will ever make me happy. This is very different from focusing on a thought that achieving goals will never make me happy. I’ll explain.

If the goal is happiness then focus on what makes you happy… …working towards goals that create a life with meaning.

Goals provide incentives to create a way of life via structure. Structure, routine and directed work (resulting in progress) create meaning. Making the transition to seeing “a way of life” enabled me to take a holistic approach to athletics. If the goal is an incentive to follow a path then the game is about the “how.” I have many roles… husband, father, teacher, coach, writer, employee, custodian, fiduciary… I meet my commitments to those roles while working towards my goals. I’m cautious about making commitments and stubborn about keeping them.

Even if goals are illusory, even if they won’t bring happiness in themselves, even if I’m going to want something different in ten years times… my current life is far better when I am engaged in a project that creates value for myself, and my inner circle.

The key is to think deeply so that I choose wisely.

That’s the purpose of my writings.

One of the great things about having friends that are older than me is the ability to access their experience. The things that bring me satisfaction in my 20s, 30s and 40s are similar but not identical. I’m not great at predicting what I’ll value in ten years time and need to be cautious with major decisions.

I’ve never had strong attachment to geography, or possessions. Earlier this year, I created a plan to move my family from Colorado to California. I started with the numbers… primarily a budget and a real estate search. The numbers showed a significant increase in my cost of living. Given that I wasn’t cash flow positive at the time, I made the decision to downsize, then reassess.

As part of my review, I considered the people in my life. A common “problem” of old age is loneliness and constantly hopping around the world makes it tougher to establish roots. Given that we have three kids, a strategic goal for my 50s is to create a life where my kids will visit, at least occassionally.

So I drew a picture – I’ve generalized into categories for this article. My original chart started with the people who are important to me and the people with whom I spend a lot of time. It took me a couple of iterations to get to what you see below.

I’ll chat you through the key parts of the wheel:

Spouse – my wife is “me” both legally and practically. That’s how we’ve set up our marriage and how I manage my life. Full disclosure and unity exposes us to risk but greatly increases our likelihood of success. Also makes it easy for me to explain my relationship, “just assume we’re, effectively, the same person.”

Kids – I’ve changed my life to spend a ton of time with my kids. With preschoolers, and spouses, I’ve found that near daily involvement works best. That said, we schedule breaks from each other. It’s always tempting not to take a break.

Friends & Mentors – I ask myself, “Who are the people that I’d travel to visit?” Even for people in your hometown, this is a good test of how much you value the relationship. If you don’t care enough to travel then you probably don’t care. Most my friends are mentors, helping me improve an aspect of my life. 

Key Family – same test as Friends & Mentors – if I won’t travel then they aren’t key.

Secondary Family – even if people aren’t key to me, they might be key for educating my kids, important to my wife or essential for the overall strength of my family. It is worth making an effort to maintain a relationship with these people.

Career / Work / Education – how do I fully utilize my skills and create a life with meaning outside of my friends and family?

Family & Business Support – I run a number of functions within my family and work life. Who are the key people that help me achieve my family and business goals?

Succession Plan – Who replaces me if I die suddenly? In thinking about the sudden death role, I consider: acceptable to spouse and family; independence; known to spouse for a long time; family connections between generations; and alignment with family values. If I live a long life then it’s up to my wife and me to guide the education of our kids (an important legacy that we will leave behind).

Community – this is an area where most of my friends have deeper ties. I suspect that community roots will become more important as I age. My strongest community is virtual yet my older pals value their face-to-face community most highly.

Once I had all the names down on paper, I wrote everyone’s country and state beside their name. As an international man of mystery, it surprised me that 90% of my spokes were Colorado-based. Most of the out-of-state connections were likely to move over a ten-year time horizon. Further, many of my non-Boulder buddies tell me that they are likely to move within five years. 

I’ve made a similar chart for places (rather than people) in my hometown. I like my life to have a high walkability index with easy access to childcare, schools, groceries, coffee, restaurants, weight training and bike routes.

This was a surprisingly useful tool to explain my life to the key people in my web. Within a family, it is surprising how little we know about the other members.

In private, I asked myself if my actual time allocation matched my life’s priorities, and those of my family. I’m laying out my next 12 months and my chart helped me set priorities.

Take time to consider who’s truly important.

Yesterday afternoon, my wife commented that the difference in my personality from April to September is night-and-day. Success!

What changed? I’ve worked with hundreds of athletic parents and the conversation is nearly always about seeking to fit more in their lives. My answer has been a devotion to less. 

I touched on aspects of my changes back in July. Cutting social networks and sitting quietly for ten minutes a day are changes are available to everyone, immediately, and cost you ZERO net time. Frankly, when you factor in all the time we waste processing social clutter in our minds, you can put hundreds of hours into your year by dumping Facebook alone.

Most people won’t be able to pull off what follows – my friends in their 60s and 70s understand my choices more than my pals in their 20s. I’m not recommending this path – just sharing what was required for me to achieve peace of mind in a house packed with young children.

The month before, and after, my move were emotionally tough. However, three months in, the family prefers the smaller, more convenient location. We’re in a rental and have been discussing where we’d like to live after we sell our old place.

But the benefit of the move isn’t in the house, or the street. The move enabled me to change the way I live.

• Three days a week, I jog a mile to my daughter’s school (she rides), we play a bit then I either walk home, or continue my run.
• I can walk to meetings and social events in downtown Boulder – I try to arrive 15 minutes early so I can walk slowly and relax.
• I take at least one kid for a walk every night.

So I’ve inserted eight walks per week of about 15 minutes duration. I’ve read about walking meditation and that’s not what I’m doing. The main benefit is being unplugged.

Unless I’m going to a business meeting, I walk without phone, watch or time pressure. Previously, I would drive everywhere because my day was crammed with things-I-had-to-get done. I now have less to do because:

• I released myself from the self-imposed pressure to perform athletics a high level.
• I accepted the possibility of a permanent reduction in my financial standard of living.

It is surprisingly difficult to train and work less. Looking deeply into my life, I saw my external successes as illusions. Still, it’s difficult to leave them behind.

The key illusions are my drive to do more and spend more time on generating external validation of my passions. Far better to do well and focus on repeating what gives satisfaction.

There is a disconnect between what I think will make me happy and what actually happens on the days when I am most peaceful. So across the summer I took notes on my good days and realized that life-is-better-when:

• I’m fit
• I write
• I’m underscheduled
• I spend time (individually) with my wife and kids
• I have a cold room to sleep in and get the rest I need

In August, my wife asked me how much I spent per annum as an elite athlete – a deeply-satisfying period of my life with immense personal freedom. I thought about it and my core expenses were $50,000 per annum.

I compared my core expenses (me alone, not with three kids) to my net worth and earning capacity. I came to the conclusion that my good days were indicating that I’d be happier living in a trailer park (with great air conditioning) than beating myself up to provide for a life that has nothing to do with what makes me happy.

It’s about this time that I started talking about living in a double-wide and having a fulltime nanny. My wife never understood what that was about – now she knows.

Over the past year, I took a gamble that if I made myself happy, I would be able to transform myself into a world-class parent and husband. In becoming a better man, I would surround myself with love and that would compensate for the reduction in external living standards.

When life is good, ask why.

I’m prone to the psychology of misjudgment (essential reading linked) and my most common trap is “if only”. A few that have visited me in 2012…

If only…

• I had a lighter bike
• I lived in a smaller house
• I had less…
• I had more…
• She joined our team
• My kids would behave better
• The world was more like me
• I was a better, faster, leaner, more beautiful…

Whenever I catch myself obsessing on an “if only” point, a red flag goes up. The next step is to dig deeper and ask “then what.”

• If I had a lighter bike then… I’d climb faster.
• If I climbed faster then… not sure (dead end)!

Most of my “if only” thoughts fizzle out after two, or three, steps.

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August 11th is the end of my athletic year so I’ve started my annual review precess. 

Pulling out last year’s review I am reminded of my Key Five (Train, Write, Marriage, Kids, Learn). I compare my Key Five against my “then what” replies, which often disappear at that stage.

At the start of this year, I was planning a sabbatical in 2013 (if only I could get away).

In looking deeply, I discovered that I was considering a path to leave my current life. When I compared that to my Key Five, I saw my true desire was a shift towards learning and writing. I’ve spent the last five months learning a new sport (mountain biking) and swapping writing for coaching. These changes avoided the major disruption of a change of hemisphere.

I should have known that the answer wasn’t waiting in Australia!