July 25, 2025

5 Biggest mistakes you make under 60

7 minutes

Garth Heckman

The David Alliance

When people are asked… if you could do it over again would you… and they say “no, I love my mistakes and its what made me who I am today”. That sounds great right, even manly… but I truly doubt it. If I could go back and do things differently would I? ABSOLUTELY 100% - so what would I do differently? Thats where were going today!

It's impossible to provide a definitive "five biggest mistakes" for every man in every decade of his life, as experiences and priorities vary greatly. However, based on common life challenges, regrets, and advice, here are some generally observed mistakes men often make at different ages:

Under 20:

Neglecting Education and Skill Development: Not taking school seriously, failing to explore passions, or not investing in skills that will be valuable later. This can limit future career and financial opportunities.

I would imagine most boys are not realizing that High School is the last free education you will get… use it up as much as you can. And more than that, learn skills from other men, its free education. Welding, automotive, investing, carpentry, cooking, baking, relationship advice, boxing, Balancing your checking account, talking to women, handling conflict… Just about anybody can teach you something for free.

Poor Financial Habits: Not learning about budgeting, saving, or investing, and instead falling into debt (e.g., credit card debt, unnecessary loans) or wasteful spending.

Here is a lesson I learned early on in life. And I will admit, that early on in life I liked to spend money on stupid stuff… or at least over spend on my hobbies. But I learned two huge pieces of advice. One give yourself a raise every year…i.e. shop for lower insurance, cable, internet, cheaper place to buy groceries etc…

2ndly I sell stuff I have not used for a year and I invest it into my 401k. Also I don’t do my own investing other then crypto. And I do not touch my investments… early on I did, but I learned the hardware. If I had kept my Amazon stock I would have a few million dollars still in my portfolio.

Ignoring Health: Believing they're invincible and adopting unhealthy habits (poor diet, lack of exercise, insufficient sleep, substance abuse) that will have repercussions later.

Not just ignoring health - but ignoring healthy habits. Build into your life a regular weekly exercise plan. Healthy eating and sleep habits. Look I get it, when I was under 20 years old I drank a 12 pack of Mt. Dew a day and ate a full bag of double stuff Oreos - now I was waterskiing and barefooting all day long so I was burning it off and I was also a competitive powerlifter… but the habit was hard to break even though I was not putting on weight.

Back to working out… most guys say they don’t have time, but if you get up at 5am you will have time, not only that you will be more energetic during the day but when it comes to sleep you won’t be able to stay up late watching stupid TV or computer or phone… so it all balances out.

Lack of Self-Awareness/Identity: Not taking the time to understand their values, goals, and who they are as individuals, often leading to being swayed by peer pressure or societal expectations.

Know your weaknesses and box them in, and know your strengths and double down on those. I am not going to spend time working on becoming more detailed and OCD… it aint’ me. I will work on being a leader, communicator, preacher, teacher, vision caster, motivator and risk taker.

I won’t allow myself to work in my weaknesses - I will let others work in those areas…and if I absolutely have to I will first build a detailed system to do it.

Taking Relationships for Granted: Neglecting friendships or not learning healthy communication and respect in romantic relationships, which can lead to isolation or repeated relationship issues.

Most men under 40 are only practicing divorce in their relationship habits. You make out, you have sex, you break up and move on. THIS IS THE PERFECT PRACTICE FOR A ruined marriage. Most guys under 20 are 100% motivated in relationships from a selfish foundation. They only give to get, they never learn to give just to give. They never learn to sacrifice in order to create a better version of the women they are dating.

Under 30:

Not Investing Early: Missing out on the power of compound interest by delaying retirement savings or other long-term investments.

If you are 25 and you invest $12 a day into an account reaping basically between 6-8% return you will have a million dollars by the time you retire. That is only $360 a month. That is nothing… if you think its a lot add up how much you spend at the convenience store, on clothes you don’t wear, on tickets, on junk food and fast food and maybe even online gambling or girls… its peanuts.

Staying in Unfulfilling Jobs/Careers: Remaining in a job or industry solely for the paycheck, without pursuing opportunities that align with their passions or offer growth, leading to stagnation.

Here is a secret. There is someone out there willing to pay you for what you want to do if you are good at it. You want to just play guitar all day? Learn to read music, join a musicians union, hang out with other musicians and producers… it is not that hard. You may not make millions, but you will earn a living doing what you love. I have quite a few friends who do it full time and part time and make decent money.

Prioritizing Work Over Relationships: Sacrificing personal connections, family time, and mental well-being for career advancement, leading to regret and strained relationships later.

I know you are under 30… you have a lifetime ahead of you… but actually you are just about in midlife. If you live to 75 you are only a few years out from reaching that half way mark.. and trust me the next 35 will fly buy 3 times as fast! So focus on relationships.. your parents, your spouse, your brothers and sisters, your childhood friends, men at church etc… make that a solid priority!

Failing to Address Mental Health: Ignoring or suppressing mental health issues, such as anxiety or depression, due to societal pressures or a "man up" mentality, preventing them from seeking necessary help.

Look its no secret that a lot and I mean most of 30 and under came from dysfunctional families. From No dads to 4 dads… It can cause a lot of stress, mental baggage and a lack of skill in dealing with it. The internet, phone and social media pressure does not help. One of the greatest manly things you can do is go in for counseling and mental health screenings. Get the help you need and don’t ever be embarrassed about it. You would not be embarrassed by going in for a broken arm… mental health is no different. And you are truly doing if for your current or future family.

Making Major Financial Commitments Without a Plan: Taking on significant debt (e.g., for an expensive car or a house they can barely afford) without a solid financial foundation or emergency fund.

Nothing wrong with buying a new car… but that doesn’t mean it has to be the brand-new or the best or even middle of the road. My car is 25 years old with 200,000 miles on it…and that car has not had a payment for 22 years.

If you are going to purchase a house, car of boat or motorcycle… talk to a legit financial counselor. You might be surprised at how much they can help you. There is nothing wrong with spending money, there are only wrong things to spend money on.

I will say this, I do see a lot of 30 and under young men who are really on the right track. They have learned the hard way from watching their parents make all the wrong and stupid decisions. Good for you! It will be worth it!

Under 40:

Neglecting Physical Health: Continuing unhealthy habits from earlier decades, leading to the onset of chronic health problems (e.g., heart disease, obesity, diabetes) that could have been prevented or managed earlier.

Here is a little bit of controversy…. And BTW I am working on attaining my certification in nutrition. You can get away with an ok diet if you are physically active. But even if you eat healthy and are not physically active - it will hurt you.

Build a system in place to do something you like to do a few times a week. Volleyball, racquet ball, jump rope, lift weights, karate, pickle ball, hot yoga… I don’t care, just do it 3-4 times a week for at least 45 minutes and your life will improve miraculously. Most people hate exercise because they choose exercise they hate. Choose something you love.

Becoming Stagnant in Career: Not continuing to learn, adapt, or seek new challenges in their career, leading to being passed over for promotions or feeling stuck.

Two things you can do to grow in your position… proven strategies. #1 learn how to get along with people. Most people are promoted first and foremost because others like them. #2 Continue to ask to learn new things at your job. Have you ever wondered what your boss would say if you asked him “what can I learn in order to help you and your business succeed.

If you are not growing you are dying. Every year you should try to learn something new. Get a certificate in basket weaving… it does not matter. Stay sharp.

Ignoring Relationship Issues: Allowing resentments or communication problems to fester in their primary relationships, rather than actively working on them, potentially leading to divorce or emotional distance.

You have not repaired family relationships and now they seem irreparable… until someone is lying on their deathbed… Now is the time.

Secondly you realize that between you and your spouse… that little issue did not go away. Now it is a monster. It could be how you flirt with other women, your anger issues, your over spending, your lack of communication…. Here is the crazy and astounding FACT - your marriage can get better and better and more amazing if you put in the hard work, or you can do nothing… simply nothing and it will suck. You don’t have to put in the hard work for it to suck… just do nothing and it will happen all on its own. Ignorance starts out as bliss but soon turns into bitterness.

Lack of Financial Planning for the Future: Not adequately saving for retirement, their children's education, or other significant future expenses, despite increased earning potential.

We covered this before but for the sake of redundancy - If you have not started a healthy aggressive retirement plan by the time you are 40, you can plan to live poor when you retire or plan on working until you are in your late 70’s. Don’t be that guy.

Failing to Cultivate a Strong Support System: Losing touch with friends and neglecting to build new connections outside of work, leading to potential isolation.

Point 2 today was ignoring relationship issues… but along with that is not taking time to build a support system. The old adage “the best way to have a friend is to be a friend”. It has stood the test of time. This week I am helping a friend move.. why? Because he has been there for me numerous times.

Who do you call in a pinch, a bind, an emergency? I can call Ty, Tim, Scott, Allan and they will help no matter what. And they have called me… and I will help no matter what!

Under 50:

Not Prioritizing Health Screenings: Skipping regular doctor's visits and necessary health screenings (e.g., prostate exams, cholesterol checks), which can delay early detection of serious illnesses.

Becoming Complacent: Settling into a routine and resisting change, whether in their career, personal growth, or relationships, which can lead to a sense of unfulfillment or "mid-life crisis."

Ignoring Work-Life Balance: Continuing to overwork at the expense of family, hobbies, and personal well-being, leading to burnout and regret.

Failing to Update Skills or keep with the times: Not adapting to new technologies or industry changes, potentially making them less competitive in the job market.

Right now you should be learning AI, crypto, Blockchain, Analytical and Critical Thinking: The ability to evaluate information objectively, question assumptions, ESPECIALLY IN TODAYS MEDIA - and solve complex problems by breaking them down and finding innovative solutions is paramount. Even advanced AI can't replicate human critical analysis.

And you don’t have to be a nuts’O prepare but how do you live off the grid or what do you do what grocery stores are out of food? You have to protect yourself… as we get older many of us have become so dependent on technology that if we had to live out in the sticks we would die.

Its never been easier and more important to update your skills in every facet of life.

Lack of Estate Planning: Not putting a will, trusts, or other estate planning documents in place, leaving their loved ones in a difficult position later.

The worst moments in life that I have seen personally is when someone dies and the family tears into each other because of a lack of planning on the part of the deceased. Everything from what you want in the funeral to who gets what.

Under 60:

Regretting Not Living Authentically: Realizing they spent too much time trying to meet others' expectations rather than pursuing their own dreams and desires.

Insufficient Retirement Savings: Facing the reality of retirement without adequate funds, potentially forcing them to work longer than desired or significantly alter their lifestyle.

Losing Connection with Family/Friends: Realizing they neglected important relationships over the years and now struggle to reconnect or feel isolated.

Ignoring Emotional Well-being: Not addressing long-standing emotional issues or seeking support for mental health, which can impact their quality of life in retirement.

Failing to Maintain Physical Activity: Allowing a sedentary lifestyle to take over, leading to decreased mobility, chronic pain, and a lower quality of life in their later years.

Not sharing Christ with those who have past on before you.

Not risking enough in your spiritual walk. Faith is spelled R.I.S.K. Have you ever prayed for a dead person to rise up? Have you ever prayed for a person with cancer? A headache? Have you ever spoken to someone a word that you feel God has given you for them? Have you called a friend out on a sin? Have you ever stood up for your biblical values at work or your network… I am pro-life. I do not agree with Transgenderism or homosexuality? I am pro Israel. I believe Jesus is coming back and you will spend eternity in Hell if you do not accept him as your Lord and Savior…

These are general observations, and every individual's journey is unique. The key takeaway is often the importance of proactive health, financial planning, continuous personal growth, and nurturing relationships throughout all stages of life.

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By Garth Heckman

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