Living With Guilt

I think that it’s natural to live with some sort of guilt. Whether it be relationship, parenting, friendship or otherwise, there are things you wish were different in your life. In my life, there are a few things I live with that I thought I’d share, because I think they’re common instances . . . and at the very least, I hope you realize that you’re not alone.

Before I get into this blog, I wanted to be clear that much of the guilt I feel is probably unwarranted, as is probably your guilt. That doesn’t make it any easier to cope with it, but I hope that by reading my situations, that you may come to grips with some of yours. It’s ok to feel guilty. It’s human. I think it’s how we deal with this guilt to better ourselves that is the mark of who we are moving to become.

I’ve been wanting to talk about this topic for a while and I’m going to touch on three aspects of guilt. Entrepreneurship. Marriage. Parenting.

With that, here we go . . .

The Entrepreneur

As an entrepreneur, I have to make dozens of decisions a days. Some won’t affect anyone but my business (which ultimately affects everyone), but some have massive repercussions to my staff, client and vendors.

I’ve gone on record saying that a business leader HAS to have the answers. We have to make decisive decisions, and then we can debrief them later. Sometimes too much overthinking can cause what’s know as “Paralysis by analysis”. This is cause when people can’t act decisively because they’re so afraid to make the wrong decisions.

I read an article that speaks about this topic called, “The Science of Analysis Paralysis“. I included the link in case you wanted to know more about this topic. It talks about the “Paradox of Choice” which means that “Less is More. Too much choice is stressful”.

I know that this is getting pretty “textbook” for a paragraph on guilt, but track with me. The choices we make as an entrepreneur/manager/boss, have to be made quickly and decisively and the science supports it. In short, it’s the “trust your gut” model, and it’s effective.

The Guilt of an Entrepreneur – HR

So knowing what I just said above, how can I feel so guilty about some of the results of my decisions?

Because I’m human.

The easiest example of guilt as an entrepreneur is firing someone. I take firing people VERY SERIOUSLY. Every once in a while it’s a joy to fire someone. 🙂 You all know what I’m talking about. But in 99.9% of the cases of people I’ve let go, it’s not that way.

As a young business owner in my late 20’s, I realized that this decision would have a sweeping negative effect on the individual that I was going to let go. It was going to rock their world and most likely their family’s world. I don’t take this lightly. But that doesn’t make me feel any less guilty when I do it. I tell myself that collectively, it’s good for the company and all of the employees. I try hard not to think about too much (analysis paralysis), but it’s still difficult.

One takeaway from these experiences is that knowing that I’m “right”, doesn’t take away the guilt. It’s just something that you have to live with as an entrepreneur/boss/manager. But I will say that knowing the feeling of this guilt, and the weight of my decision, makes me VERY THOROUGH when I’m deciding to go this route.

Make sure you’re right, and then live with whatever guilt you may feel.

The Guilt of an Entrepreneur – Faliure

One of the things I fear most as an entrepreneur, is failure. Failure to myself, but more-so failure to my people. My people being vendors, freelancers, permalancers, staff, partners & clients.

I’ve run or owned my own business for 20 years now. Just when I think I’ve seen/experienced it all, I get surprised. Only one thing is certain when running a business, and that’s that something will always surprise you.

My first business crashed and burned. I’m not going to get into why/how/who’s at fault. The reason I won’t is because I need to take responsibility for the fact that it went down while I was in charge. Doesn’t matter why it happened. It happened, and there were 36 people counting on me to make sure their jobs were safe.

That’s a tough pill to swallow. Sometimes things are out of your control, yet you are still ultimately responsible. The guilt I felt after letting all 36 staff/family members go is something I still feel in my chest as I write this. And this happened over 6 years ago.

Guilt is good in this regard because it holds you accountable. The buck stopped with me, and I let people, vendors and clients down. As I run my second business, the guilt from my first business keeps me focused and sharp.

Guilt an be a motivating factor too. Being guilty means that you’ve taken responsibility for your position and actions. Do the right thing for your people and your guilt will be for the positive. Do the wrong thing and your guilt will live with you forever.

Guilt For My Marriage – My Wife

I’m in Cabo San Lucas right now as I write this at 3:30am. I was in the pool late tonight having a heart to heart with my buddy Peter. I was talking about some of the things I’m guilty of and how sad those things have made me. That’s what prompted this blog, despite the fact that I have several others that I’ve started and not yet finished.

My failed marriage is something I’ll feel guilt about for the rest of my life. Not because I feel like I let my ex-wife down, because I think I probably did. But because I let my daughter down. And that’s something that I almost can’t bear to think about.

Every marriage is a two way street. But my guilt lies in the fact that I always wonder if there’s something that I should/could have done better. My personal guilt is usually tied up in the question of whether I did my best at something. And when I don’t, that’s when the guilt really weighs heavy on my heart.

In my life I don’t really do anything half-assed. I’m an all in or all out person. Even though I wasn’t the one who ended my marriage, and the way it ended was certainly a messed up situation, but I’ll always wonder if there wasn’t something else I could/should have done. I’ll never know the answer, but I know if I ever get married again, that I’ll not make the same mistakes I did the first time.

There’s a little voice in the back of my mind that says, “Ben, you had your chance and maybe that should be your only chance”. I tell myself that I could find love again someday, but truthfully, I’m not sure I will.

Sometimes you’ve got one shot at something, so make sure you do it with 100% of your heart. If you give it any less than that, you may end up wondering for the rest of your life, what might have been if you had. That’s when guilt become regret.

Guilt For My Marriage – My Daughter

The guilt I feel most on my heart, is the fact that I can’t/haven’t provided an “intact” family unit for my daughter. I try so hard to be a good dad, but being a good dad is only 1/2 of the equation. Some might argue that that’s enough, and it may be. But I’ve never thought that “enough” was “enough”.

I’ve often wondered if my decisions in life led me to provide a broken-household life for my daughter. I love Kailyn with everything that I am. Anyone who knows me even a little bit knows that this is the truest statement I could ever make. But I have a tremendous amount of guilt for the fact that her mom and I got divorced.

I’ve gone on record saying that “two happy households are better than on unhappy one”, and I truly believe this, but that doesn’t make me feel any less guilty about being a part of the problem . . . and not the solution.

The only thing that makes it bearable, is that I wasn’t the one who made the decision to get divorced. And I wasn’t the one who made the decision to move out of state. But that’s little consolation to me.

Sometimes you can’t avoid guilt. It’s how you live with it and deal with it that matters. Guilt about my divorce forces me to be a better person, father and role model for Kailyn. Most importantly, it reminds me that while my ex may not deserve it, she gets all my respect for being Kailyn’s mother.

Guilt As A Parent

The most important thing I’ve ever done, and most important job I’ll ever have, is being Kailyn’s Dad. I take this job as serious as I’ve ever taken anything in my life. But as a parent, I think you’ll all agree that we’re constantly feeling guilty about things.

Did we give them enough attention? Have we taught them the right life lessons? Did we remember to pack their lunch or sign their permission slip? How can I raise her to be a better human being that I am?

These are just 1/1000th of the things that I’m worried about not doing right. As a parent, there’s a point that you realize that you have an opportunity to make the most impactful human being on the planet, and the same opportunity to screw them up massively. The words, thoughts, ideas and feelings you use/portray, have a profound effect on our kids.

The comedian Bill Burr did a skit on how kids brains are basically empty computer drives. And we have the opportunity to just upload all this data to their little minds, and affect them for the rest of their life. It’s a funny bit, but so true.

When it comes to feeling guilty as a parent, I can live with this guilt as long as I’m teaching her to love, care, show empathy/compassion and be a “good person”.

The End

In the end, guilt is our conscience telling us to do better and I don’t think that’s a bad thing. What I think is bad, is when our guilt keeps us from doing the RIGHT thing.

I hope you can identify with at least one of these topics that I touched base on. Guilt isn’t bad, and you shouldn’t beat yourself up over some things. Tonight when I was talking with Peter, he reminded me that there are just some things in life you can’t change. He’s 100% right. I have to make sure I’m ok with the life-decisions I’m making NOW. I can’t change the ones I’ve made in the past.

As long as I’m making better and better decisions as I get older, and growing as a person, I’m “moving forward”. Don’t move backwards. Don’t fall victim to being reactionary to situations. It’s easy to lash out or act in a way to protect yourself or your feelings, but that doesn’t “move you forward”. Do it for your kids. Do it for your staff or just do it for yourself.

Thanks for taking the time to read my thoughts. Have a great week and don’t sweat the little stuff. It’s ok to feel guilty, but don’t have regrets. Keep moving forward!

Your Friend,

If you’d like to connect with me or have a topic you’d like to hear about, shoot me a message or connect with me @KailynsDadBlog on Facebook or Instagram.

Success! You're on the list.


1 thought on “Living With Guilt

  1. Ben- I zeroed in on this sentence for some reason….”Even though I wasn’t the one who ended my marriage, and the way it ended was certainly a messed up situation…
    You didnt write “the” or “our”… this makes me think you take too much of the burden of divorce failure. I too was divorced a long time ago and I thought I was going to literally die. Remember it takes 2… equally. ( I learned years later). The ebb and flow of the relationship is a roller coaster but in the end it is an equally 50/50 separation regardless of who initiates, regardless of the words used, who left, who stayed, and who won more… 50/ 50.

    Lastly, your family is complete with you and your mom. I wish my mom was still alive. That is the best family! Happy Thursday- your friend Tara

Leave a Reply

Your email address will not be published. Required fields are marked *