44 Ways To Live and Die With Regret

Regret will eat you alive.

We’ve all felt it, the sinking feeling of “what could have been” —the decision that felt uncomfortable at the time and yet we knew was right for us.

We tend to regret the actions, choices and decisions we didn’t make.

In this post, I’ll share 44 ways to live and die with regret —so you can avoid these along your path.

1. Choose the path someone else —including society, family and friends have laid out for you instead of what you really want.

As the brilliant Joseph Campbell once said —if you can see every step of your path, it may not be yours. Spend the time and work most want to avoid through distraction to answer the ultimate question without apology —what do you really want?

2. Put everything off until “someday” when life gets less hectic, when you have more money, time, and energy.

There will never be an abundance of time and energy waiting for you to start the dream. This is not to say there aren’t more convenient seasons —but as Lisa Nichols once said: your commitment and convenience can’t live on the same block.

3. Seek approval from those around you —and check off societies boxes to be accepted when asked what you do.

For a a while, yours truly was on a one-way path to Wall Street despite having zero interest in the industry —and to be honest, questioning its entire moral compass. And yet, I found myself with a job offer at a wealth management firm after a successful internship. Hello, approval.

4. Never question anything or take time to face the questions —why am I here, what is the purpose of this, what is the meaning of life?

An 80-year longitudinal Harvard study on fulfillment found that the desire to wrestle with the questions above —and seek answers —directly led to a more fulfilling and rewarding life.

5. Fill your life with distraction and noise. Obsess over current events, political gossip, sports radio so as to never have time with yourself.

When I was most lost in life, I could receive every player on the Indianapolis Colt’s roster —including height, college, position and jersey number. There is nothing wrong with sports, Netflix or even news. But when we use it to fill a void inside of us, we always lose. Distraction soothes the pain of untapped potential.

6. Chase the illusion of safety and security —a life of comfort that is easily digestible, yet would sicken the version of yourself who had dreams, a vision inside of them.

As David Kekich one said —the incredible writer of the Kekich Credo’s —security is he lowest form of happiness. Instead, choose growth, freedom, the part of you who craves novelty, adventure, the thrill of being alive.

7. Avoid listening to your gut feeling or intuition and instead always choose the safe, logical and rational path at every mile marker.

You already know what to do. You already have the clarity you need. The question is simple —are you willing to listen when it doesn’t make sense?

8. Believe that an employer has your best interests in mind; that they will take care of you and not leave you on the side of the road.

Most of us learn this the hard way —no employer is ever loyal to us. The days of relying on an employer for our financial security are long gone. Especially for those in public companies who value shareholders over their own employees —you must become your own economy. Learn skills that make you self-reliant and give you options.

9. Chase down someone else’s version of success —without ever defining what success looks and feels like for yourself.

The first question on the Academy podcast has universally been —what is your definition of success in life and business? I ask this because without a guiding compass, we may chase the default definition that society has laid out for us at the expense of what we actually want.

10. Believe in your excuses and allow the smallest part of yourself to always stop you from action; telling you that you’re not “ready”.

We tell ourselves stories or narratives —that shape our worldview. Excuses can take control of the steering wheel if we allow them too. You’re not good enough. You don’t have enough degrees. You aren’t from this country, so how could you succeed?

11. Live in the world of ego —wanting to be right, having a fixed mindset, seeing other’s success as a reason why you can’t do it.

The number one rule of all my coaching programs is simple —drop the ego. This isn’t easy and it’s why most people say they want to change, but never do.

12. Trade your freedom for a paycheck your entire life instead of crafting a life on your terms.

There is nothing wrong with being an employee —and there are some deeply fulfilled and inspired people who work for others. This isn’t about that, rather, it is about a conscious and intentional choice to discover what you authentically desire and then crafting a life and business around that.

13. Not telling someone how you feel when you’re with them. Avoiding eye contact for one second past uncomfortable.

Allow your human-ness to shine. Say what needs to be said. There is nothing more liberating than squaring off with the emotions of our lives and putting it all out on the table.

14. Thinking you need another degree, certification, training or more education to start —and waiting for permission.

This is why I wrote the Leap Of Your Life —I’d talk to talented, skilled people who had bold aspirations but were in a never-ending holding pattern. On a long enough timeline, fear will always win and regret will be guaranteed.

15. Avoid the inner work of creating a rock solid relationship with the only person you’ll be with your entire life.

A client was struggling with this concept the other day —and I advised them to text themselves every single day for the next 90 days with a message of appreciation or write their future selves an email. We so freely give our love to others —but what about the person in the mirror?

16. Never question your beliefs, narratives and hard-wired perspectives.

The unexamined life isn’t worth living is what Aristotle said. What he meant is living in ignorance isn’t living it all —and questioning our beliefs, rules and hard-wired perspectives is the path to liberation.

17. Believe there is a mythical oasis of “arrival” —always missing the present for some far-off, distant future.

I hate to break it to you —but there is no “arrival” moment where all of the parts that make you human, the awkwardness, the messiness, the emotions —will be gone. Don’t get me wrong, your vision will fundamentally change you from the inside out, but you will still have blind spots. We all do.

18. Always move the “goalpost” of your goals back —arriving at a target, goal or dream you wanted never taking time to celebrate.

When people tell me this —I shudder. Sure, you may be an achievement machine, but this is how you live in lack for your entire life. You are always focused on the gap between “here” and “there”. I don’t know about you, but I’m pitching a tent at the goal post and having the time of my life. Music, cold beers, you name it.

19. Operate under the model of doing more so you can “be” more instead of ”being” more so you can “do” with intention, peace, clarity.

Who are you when you’re not doing, grinding, hustling? This is the ultimate question for my ambitious folk; which I am certainly a part of. However, when we tap into our “being”, we release the dark side of achievement and instead operate from a place of alignment.

20. Wait until rock bottom to change a part of your life that isn’t working.

Rock bottom is a powerful place to compel change, but it’s also excruciating. Use the tool of reverse visualization I detailed in the Leap Of Your Life to use your imagination to create urgency now.

21. Living in denial of reality —avoiding looking in the mirror and being honest with yourself about where you’re at.

Denial is choosing a life that you don’t want —day after day after day without anything changing. We’ve all been there, and it leaves us emotionally hollow, robbed of our agency to make a new choice and the sinking feeling of regret.

22. Letting FOPO —fear of what other people think—drive your decisions and choices.

The unavoidable reality is you and I will be judged if we play small and never do anything —or if we put ourselves out there, shine our light and gifts and aim to reach out innate potential. Judgement is part of the human experience, so why not do you fully?

23. Forget that you can choose a radically different life experience right now. It is never too late.

I’ve worked with people in their late 60’s starting a new dream. It is never too late —as long as you are open, ready and willing. Use past regret to make a new choice.

24. Think enough achievement and external markers of success will fill the void of untapped potential.

There is no doubt achievement and progress can create emotional freedom —but not always. Especially when one is not aligned, say, chasing a career for external reward so as to be fulfilled “one day.” As I’ve always said —fulfillment attracts achievement, but not always the other way around.

25. Label yourself inside of personality boxes —creative or logical, introverted or extroverted.

I don’t believe in personality tests. Besides the shoddy science and gross simplifications, I believe they put is in boxes that become prisons. We label ourselves shy, uncertain, creative or not —and these dictate our lives. Case in point, for 27 years I never thought I was creative. Now, I use the word every day.

26. Watching television for an entire lifetime —wasting hours a day on escapism instead of living a life that you want to be a part of.

I’ve always found it curious that we design our homes facing the television and we give it our most prized resources, which are time, energy and attention. If you could know everything there is to know about Game of Thrones or build a thriving life, which would you choose?

27. Living vicariously through 24-year old gladiators on Sundays, Hollywood stars and entrepreneurs on social media.

On that note, use others to inspire you. Watch documentaries to lift you up. But at some point, we must ask ourselves —are we watching other’s dreams as inspiration or to vicariously live through their highs and lows so as to fill a void in our lives?

28. Living in the past, being addicted to drama, gossip, how someone wronged you, even the victimhood of trauma.

We all have trauma. We all have hurt. We all have sadness. And if you’re there, my heart goes out to you. Allow yourself to feel. Allow yourself to grieve. But remember —staying there for an entire life and playing the victim card is tempting but robs you of your true power.

29. Staying stuck to your comfort zone —instead of choosing to get uncomfortable every single day to feel alive.

The ego and our comfort zones are the best of friends. They use one another to stay stuck and keep us exactly where we are today —even if it’s not what we want. At best, they rob us of potential. At worst, they destroy our dreams and keep us in misery.

30. Never owning your worth and value. Not putting yourself out there for that dream opportunity.

What do you have to lose? What would you do if you weren’t afraid? What’s really the worst that could happen —you get a door slammed in your face, you get mocked on Twitter and someone leaves a passive aggressive comment on your Facebook wall? It’s not as bad as you think.

31. Waiting to be “discovered” —instead of doing what Steve Martin said which is to be “so damn good they can’t ignore you.”

No one’s finding you at Starbucks anymore and writing you a million dollar check. Instead of waiting for someone to fund your dream —take ownership. Study a craft. Acquire skills, fall on your face. Endure the messiness of growth.

32. Letting social media algorithms, misinformation, fake news and 24/7 stimulus rob you of your peace.

I’ll be honest —this one saddens me. I am seeing talented, skilled and good people who are being taken on a carnival ride by social media, fake news and conspiracy theories. And let me be clear here —I’m certainly not immune. But please, for the sake of your future self —tread carefully here. Limit your inputs and protect your peace like your life depends on it. Because it may.

33. Not understanding there are windows of opportunity in life —when we know it’s time. When we miss these, they may never come back.

There may not be another chance. When I met my now fiancee, I didn’t have a second opportunity. We crossed a road, I had 11 seconds —and then she’d be gone. I share this with you because our ego can talk us into avoiding an uncomfortable move today with the hopes that tomorrow there will be another one —but windows of opportunity close and we may never know what could have been.

34. Going to Law School because it’s “next.” Getting married because everyone else does. Having kids because you’re 33. What do you want?

You don’t have to follow a path that screams validation and approval. You don’t have to do what all of your college buddies are doing. You don’t have to complete any of the “mile markers” on the marathon of a standard life. Now, if you want these things —go all in. But take a moment and reflect. What do you want? There are countless paths to a fulfilling life.

35. Forgetting the truth of your capability and the power you have inside of you —and never letting it come to life fully.

Capability is an emergent property. What this means is simple —it comes out when the conditions allow it to. It’s your performance when you’re on deadline. It’s your physical tenacity when someone you love is in danger. Which means we must create conditions of capability, otherwise, we never maximize it.

36. Never thinking about death, mortality, how you want to live the “dash” between your birthdate and when you are no longer here.

The dash is all we have —what will you do with that real estate? Mortality is not a bad thing —it is part of life, as natural as life. I have a wristband and hat in front of me that both say 86,400. Why? Because today may be it. When we face off with this truth, we remember what matters. We say what we need to say. We leave it all out on the field of play.

37. Not having a life philosophy; a set of principles that guide you and ensure you stay on course with who you want to be.

For years, I’d carry around a set of principles in my wallet. I posted them on my car. I wasn’t living them every day, but I was striving. As I grew, it allowed me to identify a life philosophy, a North Star on who I want to be. We should all do this work, as it pays off in droves.

38. Not making the bold leap before you’re ready —letting the ego tell you to wait until it’s a better time.

The ego will come up with a litany of excuses that make no rational sense and yet sound like undeniable truth. I’m here to tell you a simple fact: your audacious move will never feel perfect. There is no “right” time. Life will not get less busy anytime soon. What are you waiting for? Regret stings.

39. Thinking growth is linear and giving up in a deep valley before your next breakthrough —not knowing what was waiting for you.

Growth is a hot mess on a Saturday night after four tequila shots. All of these curated, 18-minute TED talks are actually doing you a disservice. Your path will have countless dips, peaks, valleys, rock-bottoms, riveting highs, mountaintops. This is the truth; growth is messy. Anyone who tells you otherwise is flat out lying to you and should not be trusted.

40. Spending your whole life working towards an oasis in the future and then realizing you missed the best times of your entire life.

You will never be as free as you are right here, right now. Sounds crazy, right? Well, the truth is, all we have is the moment in front of us. Most successful artists, creators and entrepreneurs look back at when they started and say it was the best time of their lives. Don’t miss right here, right now.

41. Being resistant to change; evolution; the expiration of relationships, old friends, what “used” to be and forgetting we live in a natural world.

Change is constant —and yet we resist it. We will lose people; relationships will expire. We will shift identities, we will change what we value and who we are. Embrace change, seek it, and don’t lament it. Be open, ready and willing.

42. Obsessing over current events instead of living your life. There has always been chaos, war, unrest.

Especially in a society soaked in misinformation, this is dangerous. I am not saying to not be informed, but imagine the growth you could crate in your life without an incessant ned to check news, updates and current events 24/7?

43. Not seeking what makes you feel alive, present, plunged into the “deep” now and building a life and business around that.

When was the last time you felt fully alive? When do you feel most engaged? What would you do if you had unlimited resources? I am writing this on a Saturday morning at 5:50AM. No one is telling me to be here, but I choose to be. Find that for yourself.

44. Waiting and not recognizing the 86,400 seconds in a day may be your last so you might as well jump off the cliff into the deep end.

Today is all we have is not a cliche posted by a pseudo-influencer on Instagram, it’s real life. The moment you own this fully, you step into the present moment and leave it all out on the field. Say what needs to be said. Take a chance! Change one thing you’ve been putting off.

44 Ways To Live and Die With Regret Resources & Links

Here are some of the best resources to help ensure you do not live and die with regret:

• The Leap Of Your Life

• The 1% Rule

• Seneca, On The Shortness Of Life, BrainPickings

• Steve Jobs Commencement Speech

• TIFU —My Regrets As a 46-Year Old

• Top 5 Regrets Of The Dying, Bronnie Ware

• One Last Talk, Philip McKernan

Regret can be a bitter pill to swallow —we’ve all experienced it in the past.

But it can also be hopeful and ensure we make new decisions and choices today.

Personally —moments of regret have woken me up to get uncomfortable, to stop drifting through life and actually get to know what I want and who I am.

Which one of these connected with you? Post to comments!