The Sketch Guy’s Most Valued Lessons Still Sting. How About Yours?

I regret not taking more risks; I regret what I could have done and might have been.

Everything else comes down to that - not having the self-confidence to say to myself that I would be able to correct any ill-effects, whether it be a lost job, a failed coffeeshop, a lost friend.

And I'd like to say I've seen a lot of wisdom in the posts I've read here.

Love and family count for much more than dollars and cents can ever approach. My great wish for everyone would be that they all have $10 million dollars at some point in time...and literally see that not only does it not make them happy, but that it can make themselves -- and the people that matter to them most -- miserable. A lived fact.

this dovetails nicely with your latest piece on luck. fir those who havent read it, it posits that many successes in life are determined by nothing more than luck. this idea has goes by many other names including "being in the right place at the right time" and "picking your parents right". the later is also a two-sided coin as I recently found out.

probably 50% to 70% of my successes in life were probably due in some part to luck. but the term I would rather apply is "opportunity" (a way of thinking I learned in a job I absolutely hated but didnt know it until I was already there but they came to me and I thought I was "lucky"). its what you DO with the opportunity after luck has shined its face upon you. some people who are "successful" just have a better track record of picking up and running with whats given to them than others. and this is where even if you dont "make your own luck" that any talents you may have for whatever task is at hand, show thru. it is then after producing results, that you earn your badge of courage or your scarlett letter. and if you learn from that letter as this article suggests, you are in fact truly blessed.

"making your own

Money is security, not spending power.
Acquiring assets multiplies the value of your time.
Assets that don't pay, become liabilities, get rid of them.
Lucky and unlucky occur equally, good decision-making (gained from education and experience) along with savings, enhances the impact of lucky and diminishes the impact of unlucky.
Always, 90% of life is just showing up, to be there when opportunity knocks.

I started making a list of experiences, and realized each lesson was embedded in a certain context, and that context was a commitment to a relationship: being a parent, being a husband, being a friend, being a business partner, being a boss, being a teacher, and so on.

Always assume the other side of a financial transaction is out to take as much financial advantage of you as they can in a given situation. The implication of this is context dependent: a car dealer will misinform to the degree a sale is necessary but he may hope for return business so limit his sharp practices, obviously less so for used car dealers. The one off contractor will suppress vital information, or do the minimal amount of work, in proportion to the degree that they have a certain reputation to maintain. Trusted family lawyers MAY provide good advice in that they have an interest in maintaining a long term income flow; many highly "respectable" lawyers will offer cursory, superficial advice if they do not see you as a source of . Similar considerations for stock brokers, except their short term financial interest predominate to a greater extent.

With co-workers, partners, even employees (unless you have direct and immediate control over their job security and remuneration), the same applies though mainly to the information they will supply: information is power and to the extent that these people control information not immediately accessible to you, they will in many cases suppress information not in their own interests.

There are of course some exceptions to the rule - a few people are intrinsically honest in their business dealings with you, but these are the exceptions - and you would do well to assume they do no exist until proven otherwise.

Stupid: Invested all our savings in a Savings and Loan credit union that offered a super high rate of return--something like 10 percent above everyone else. Lost it in the S & L crash.
Lesson Learned: Read the situation. Use common sense.
Best advice: Your best investment is in yourself, through lifelong learning, reading, listening.

Mark's comment about cherishing the "near misses" reminded me of something that happened over 50 years ago that I've never forgotten. It was a rainy halloween night. I was 10, taking my 7 year old brother with me to trick or treat. A car was coming but I wanted to get to the other side of the street, so I ran across. Unfortunately, my little brother followed. Tires squealed, the car hit my brother and knocked him down...gently. He was OK, but I was affected for life. We are not just responsible for ourselves. Our actions can lead to horrendous, or wonderful, unintended consequences for those we love. Cherish the "near misses" and learn from them.

Believe in God but dont rely on HIM. Love your kids but let them learn from their own mistakes. Work hard but take time for needed recreation. Stay committed in marriage unless the relationship is doomed.Save enough for retirement but dont let your life be ransomed to an unknown future. Explore your sexuality
but within the confines of even the most dreary marriage. Be committed to your work but stay open to better opportunities. And above all, do the right thing unless it is the wrong thing.

Talent without ambition (in a positive sense, striving to do better) does not allow one to achieve as much as possible. Ambition and risk taking are related.

It's never what you worry about.

Early on I thought most people like me over-simplified the complexity of investing so I could do better by using my own customized, just-for-me strategies. Like stock options. (Ouch!) Or frequently adjusting my holdings. (Ouch again!) I've done a lot better by, first, admitting that investing is indeed complex so go with the long-term not with micro-management and, second, trust firms whose products are based on sound academic research packaged into sensibly explained funds: Betterment and Vanguard (www.able2pay.com has a good article, "Best Funds 2016," comparing these and other firms, plus some useful calculators).

Spent ten years of my career in the rust belt believing that the life I grew up with would come back maybe next year. Finally cut my loses, went back to zero and moved somewhere promising, to build my career over. Best move I ever made.

I grew up poor, on welfare in East Harlem to a single mother who raised us in community full of drugs, urinated elevators and stairs, gun violence, etc. My mother had very little education, no money. I was fortunate to barely complete high school in NYC at one of the worst high schools and wake up in one of the worst community college in Manhattan. I graduated with a B+ in 1978 at age 20 and had a son. Something CLICKED and I decided, at ALL EXPENSE, to continue all the way through my masters in computer science, and 2 more kids, all in Manhattan while living in public housing and driving a yellow cab late nights. I made a lot of money after I graduated and blew it. At age 49, I went through a major, stupid financial crisis, and told myself I NEED TO DO BETTER with my money. I also had an MBA from Johns Hopkins. In the last 10 years, I put away about $600K and have a goal of about $2M in the next 12 years when I plan to stop working at age 70, get my Social Security, live until about age 95 and burn through about $5M of 401K money and pensions. I got rid of my house at age 57 and moved into a 55 Plus community saving me about $20K/year in cash and not needing a promotion so I can focus a lot more on my health and less stress. I leave to the Carribean in a few days, a Panama Cruise in April, and 15 days in Europe in June with my 3 teen grandchildren. Life is great! Don't be stupid with your money, and my vacations are low-cost and well planned.

The best thing I can cite is how often I remember things I was told by someone with whom I had a very difficult and contentious work/education relationship. This person, long dead, and I agreed on almost nothing, but one of many wise things he passed along to me was this. "When I start thinking I'm really smart, I start looking for what I'm missing."

Prior to retirement, I may have spent too much time ensuring that funds were available "later", which sometimes blinded me to life-enhancing opportunities in the remaining now. I am getting better now.

Holding on too long to situations that are no longer working. Stop struggling, let it go, stop thinking you can fix something that refuses to be fixed. Move on and accept that most of us have little control over other's behavior. Create a new situation that is more amenable and stop hurting yourself. Self-inflicted pain is not healthy or beneficial to the world.

It looks as if nearly everyone agrees that we learn most from our mistakes. I agree completely. I'll be 69 in a week and the two most important things I've learned so far are not to push too hard to make things come out the way I think they should because there's often something better that I hadn't thought of. Second, don't try to change people because it can't be done; learn to find what you like in each person and try to ignore what you don't.

Travel to a dramatically foreign culture.

Remove the q-tip before answering the phone. If it's raining, sometimes it's best to leave the umbrella behind. Be careful not to take a stranger's remarks too literally.

If he tells you he's a jerk, believe him and run.

What stings? Looking back on an adequate life. I was sure my judgements were correct & so proud of avoiding big risks. I'm financially OK, but the by- passed opportunities were many. Landing on my keister at 55 finally shook my total faith in myself! Now I reach for the next branch, not knowing how it will go...

People are complicated. Even the complete jerks in your life can offer wisdom, aid or comfort. Just don't, like, hang with them too much.

I have learned to be gentle with myself and with others, there is no gauge by which life is measured. No winners , no losers just people on different journeys with different lessons. I used my anger as a shield to keep away that which I could not or did not see the value of. I now see lessons instead of conveniences, Everyone has something to teach me, I just have to listen carefully. So much of the misery in my life was caused by my desire to fight and be strong, but why fight when a bridge and a helping hand will bring love into your life. It is so much better to be gentle, then to be strong. That lesson took a lifetime to learn.

We can look back at many instances in life and realize we were either blessed or just plain lucky, but there is the constant nagging thought things might turn out completely different the next time! We cherish those "near misses", apply the knowledge learned to our children and grandchildren so hopefully they can avoid our mistakes.

If one survives them and if one is open to learning from them, then yes, the hard times in life teach valuable lessons that increase one's wisdom. I do not want to list my hard times, the ones in my vault. They are very personal. I am still alive and still having some hard things happen to me. My learning is not finished. Sometimes, I had to make the same mistake several times before I learned to avoid it making it again.

I have a sister who is gifted at turning her hard times into funny stories when she eventually talks about them. She can be very entertaining. Plus her way of coping with her hard times becomes a lesson for the rest of us in the family, told in a way that leaves us laughing instead of crying. She has been layed off more than anyone in the family but she always finds another job. She has a gift for that too.

Spend less than you make, start saving for retirement early and when buying items that last longer than 3 years --buy the best quality you can afford. (sinks, tubs, cars, stoves etc.!)

Never let someone else have total control over your finances. When I was married the first time, I was all too happy to turn over all financial control to my husband. We had join accounts for everything, and my paycheck was direct deposited. I didn't even know how much money I made. When our marriage ended, I was at a complete loss and terrified. I didn't have access to any money for my lawyer and had to depend on my estranged spouse to pay her retainer. It was humiliating and dangerous. I had thought I wasn't really capable of managing my own finances, but after my divorce, I learned I'm actually quite good at it and rather enjoy having control over my own money. I'm getting married again, and we will maintain separate financial lives, except for a joint checking account we'll use for shared expenses, and perhaps joint tax filing.

I think part of the problem is that stupid mistakes often produce instantaneous learning. Conversely, smart decisions often take years to produce results. Sticking with your piano lessons and practicing a lot produces a helluva good pianist... in about 12 years. Stick your tongue onto a frozen flagpole and you learn immediately not to do it again.

Every job I ever had, I got laid off due to mergers. Lesson: your company doesn't care about you, start looking for your next job while you're at your current one. Every relationship I had ended because I didn't really listen to what she wanted. Lesson: stay by her side and place her needs above yours. Finally, peace of mind and a clear conscience trumps momentary pleasures and satisfaction. Thank God, because things could have really turned out for the worse.

This may depend on whether one has the right attitude or skill to draw a useful lesson from painful experiences.

Treat others as I wish to be treated.
Live _my_ life consistent with _my_ values.
Share my unique voice with the world.

Taking risk is an important part of improvement. Failed experiments and partial successes give us the opportunity to answer the four most important questions, answered in the following order.
1. What did we/I do right?
2. What did we I do wrong?
3. What do we/I know now that we did not know before?
4. How are we/I going to do things different in the next go around?

I learned not to derive my sense of self-worth from my work, or more specifically any employer. I operate from the assumption that the businesses I work for do not care about their staff, and will fire me or anyone else if they can save money doing so, or even on a personal whim. Over the course of a year I juggle five different jobs, in the spring and fall all at the same time. It is a lot to manage, but I feel safer. One may end, but I have others to fall back on. I used to have three, but one wasn't doing well, another was in turmoil and I lost shifts, so I added others. One of my characteristics is loyalty, and in our economy, that's a weakness. I've learned that if better opportunities come along, take them and do not feel any obligation to a current employer. They'll manage.

This has also made me a much better saver since I do not feel comfortable without a big cash reserve. In the end, what I really care about is that I have a happy marriage and great friends.

One of my most valuable life lessons was when I attempted to be funny and made small joking comment during a meeting, only to have the director his secretary stare at each other in stony silence for several seconds. I realized immediately that I had made a mistake by wasting their time during a business meeting. I was dead serious and on point afterward, but the damage was done and it was clear I'd lost their respect. This was a freelance job, and they didn't hire me again after that. It's been probably 25 years since it happened and I still cringe inwardly when I think about it. I learned much that day.

Back in my misspent youth, I was hiking the Appalachian Trail for what was supposed to be a week with a good hiking buddy. The weather forecast was for dry weather all week, except for rain our second night out. We were going to be around a rocky area that night with plenty of opportunities to create shelter with just a ground cloth, so we decided not to take a tent & save some weight.

The first night, high on a ridge-line of the Appalachians we laid out our ground cloths & sleeping bags and ran lines over us between trees so, in case of drizzles, we could toss a poncho over the line & make a crude A-frame tent. At about 11:00 PM, we both woke up to a torrential downpour. Our sleeping bags were sopping & we were sitting in 2 inches of water. Thunder and lightning were everywhere. Lightning struck a tree so near we could hear the wood fibers breaking before the tree came down, missing us by 10 yards. We decided we were safer staying put than trying to evacuate, so we slipped our ponchos over our heads & sat in complete, chilling misery through the night. At about 5:00 AM, we split our only tropical chocolate bar & while we were eating it, we both simultaneously broke out laughing. As miserable as we were, we knew that the minute we were dried out and in another set of clothes, this horror would be transformed into a "great adventure" in our perception (which it still is). Our lesson: we realized then that most adventure is simply misery displaced by time

Finally learned this lesson at age 57- never let fear of the unknown, fear of change, or the fear of trying something new immobilize you. My Mom tried to tell me this, but evidently I had to learn it for myself. For life does continually present opportunity in the form of the unknown future, the inevitable change, and new hurdles. I took a step and finally made a career move, and now I can see the time I wasted in not taking advantage of this opportunity, simply beacause I let my fear control me. Stop doubting yourself! All things are possible but you must take the first step.

Thank you for asking this Mr. Richards -

As a 55 year-old, I, too, feel that my most valuable experiences are the most painful; every job that I have ever had, save for the current one, I have been fired from because I was gay. The life lesson, and what I find of value, is that in each case I developed more strength to rebound each time allowing myself to develop one hell of a muscle when it comes down to standing up for myself, and refusing to act like a hypocrite. I am able to feel some pride in this now as I write.

Consequences teach lessons, which is why so many third generation businesses fail ("shirtsleeves to shirtsleeves in three generations"). Wealthy 2nd generation parents protect their kids from consequences, using their money or influence to escape consequences (and their lessons) with misguided love. That hard lessons might end up being the most valued in hindsight isn't really surprising.