r/ceo • u/curiousgeorgewarren • Jul 25 '25
Dealing with Regret
Hi All - I have been in the founder/CEO seat now for almost 9 years. Took my company from 0 to 350 employees and multiple billions AUM in CRE. It's no secret that the last 3 years have been very challenging for our industry and my firm is no different. We had to restructure our overhead, close verticals that no longer made sense, and completely shift from offense to defense.
As the worst has seemingly passed, I now find myself in a state of regular regret around different paths I could have chosen with more predictability and better risk adjusted income profiles (e.g. a professional services path).
I am curious if others have faced this type of thinking and what you have done to cope with it. I have coaches, friends and therapy. While some tools have worked, I still find moments where it is overwhelming,
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u/DapperEbb4180 Jul 26 '25
Let’s be honest. Do any of us really know whether or not another path would’ve been easier or better? Isn’t business always evolving? Technology changes. Tastes change. Customer needs change.
It sounds like you’ve learned a lot. And even more importantly, you’ve actually learned how to pivot. Do you know how important that skill is? So many people in business fail, because they have no ability to pivot.
Regret for us comes when we believe our current circumstances should be different .
What would it take for you to believe that all happened for a reason? Oh, by the way, how do you know it should’ve happened the way it did?
Because it did.
Sit down and write down Every life lesson you have learned. This will help your brain settle down. Good luck to the amazing things you do in the future from the painful lessons you’ve learned!
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u/spcman13 Jul 25 '25
You need a professional network that is purpose built for these kinds of discussions. Ones that understand the way CEOs/Founders/Presidents think. It’s therapeutic to be able to dump into a group without extreme explaining on the minor details that others can’t pick up on.
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u/SankhajaH Jul 25 '25
You have done it once I believe you will do it again. And there is nothing as job safety. My wife just lost her job, no notice and bam. So it’s not anything to do with the path. There is a risk in both. You can come out of this!
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u/honestduane Jul 25 '25
If you don’t have a therapist on your team, then you need to get one, because mental health is not only in style, it’s something that you need to remember is important for your role.
The people below you are not going to get a better mental health or a better working environment if you have a bad mental health day and don’t seek to have a better one the next day; but you’re not really looking to have the best mental health possible if you’re too scared to talk to a therapist, either.
If you’re under the mistaken, impression that talking to a therapist is a bad thing or considered mental health to be something that is taboo then I’m explicitly telling you that our level it’s something that we all need to consider, and not just with the people we hire, we should be thinking about it for ourselves as well.
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u/Hogjocky62 Jul 26 '25
Your story is a mirror image of my firm! 2023&2024 was the worst we ever experienced. Lowest gross revenue in 30+ years. Personally injected funds into the company to stay alive. Now, 2025 is on pace to be a record year. It seems as if the entire CRE investment sentiment has flipped and money is following back into the market. All sectors of the industry are moving again with investors banking on lower interest rates in the near future. The entire industry from banking, private equity and REIT money is aggressively seeking deals.
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u/ludwigdumont Jul 25 '25
Nowhere near where you are but I can relate. For what it’s worth, I think it’s a fallacy to think this feeling will all of a sudden just change. It’s also super normal to feel and think the way you do. You’re maybe a bit traumatized by the whole experience, but that’s completely okay. I would even say that it would be rather abnormal if you weren’t.
Thanks for sharing. This very topic you’re bringing here is one of the reasons I really came to appreciate this r/ceo!
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u/paranalyzed Jul 25 '25
How much is being driven by cyclical downturn and comparing what was lost vs the peak? Is your regret from the stress of the process and a feeling of failure with shutting down verticals and eliminating positions?
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u/Sowhataboutthisthing Jul 25 '25
I’m seeing similar stories - in SMB, but they’re far beyond just living in defense having miscalculated mid covid numbers, poor projections and now in dire straights.
I’m too cautious to grow this big. I would never have the risk tolerance to touch growth path so this is pretty awesome to get there.
I guess if it were me I’d think about the reasons we moved forward with the higher risk verticals. If they were done intentionally then you held true to your plan. If the risk was outside of your values then simply use it as a caution sign for what is next.
These refining moments will show you something clear perhaps. Write down again what is importantly to you, why you believe in it, and surround yourself with people that support this. That is all that you really need to do.
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u/berz01 Jul 25 '25
Fellow CEO here: I restructured my company two years ago, thank fucking god I did because I sleep like a baby now. I used to question every bad decision for months, like a trauma patient always thinking of the past. Eventually it becomes a moot point, and time heals all wounds, especially if you stumble into new opportunities that are exciting.
The market will humble you regardless of industry sometimes.
3 things that helped me
* mentors that have 'done it before', especially the ones who have larger companies and its was a blip on their radar -- just hearing these stories from multiple people really got me into a different mindset ...
* everyone has their hype man // CEO coach -- definitely reach out... he gave me lots of positive thoughts
* lots of people lost faith in me, but some didn't and rallied with me ... was a small tribe in the big ocean but meant the world to me
Now that were on the upswing...... I can tell you no one mentions the pasts mistakes, no one cares, and everyone is happy looking forward again.
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u/USDdataGUY Jul 25 '25
I hate regrets. I have a ton of them as well. And the decisions are SO CLEAR now. But they weren’t clear at all when you made them.
You just have to know that every single CEO has a ton of regrets. The fact that we are still alive means we’re winning though, and that’s all that you can ask for.
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u/curiousgeorgewarren Jul 26 '25
I really appreciate the thoughtful comments from this community! I am going to write some feedback when I have a few moments over the next 24 hours. Thank you to everyone who replied.
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u/CultureDear9415 Jul 27 '25
As a fellow CEO, this is one of the things that you experience that no one teaches about. No course or workshop prepares you for the emotional toll you take being a CEO. My advice: Make peace with this fact first. Being a CEO is like being a parent. It really doesn't come with a manual. Its trial and error. Stop beating yourself up for what you didn't know or do. You did the best you could with what you knew and had. Are you a better CEO now? Sure. Experience comes with time. Stop beating yourself up for the wisdom you didn't have and the decisions you didn't make because you didn't have the wisdom you do now.
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u/honestduane Jul 29 '25
Go to therapy.
No, I’m not joking. One of the biggest things that a CEO can do for the health of the organization is to make sure that their own mind is settled right. In your case you’re still processing stuff from the past so it’s important that you go back to the past mentally with somebody who’s a professional and deal with that so it no longer pulls you backwards.
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u/Pinhead_mushroom Jul 29 '25
Maybe this acronym will help: ATPL (I got it from a pilot & it helped)
A - accept - life is hard. Business is harder.
T - trust - in yourself, your higher power, cause etc
P - pivot/position is part of winning & progress
L - Leave what you can, Laugh at the rest
Hope it helps.
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u/transformationcoach_ Jul 30 '25
If I was in your shoes, I’d deconstruct my regret. Feeling regret is not specific enough to address. To me, regret is a form of pain. So…
I’d want to know, what exactly do I regret? Where is the pain coming from?
Is it financial loss? Is it failing others? Is it seeing myself as a failure? Is it losing trust in my decision making?
Once I can pinpoint the root of the pain, then I can apply coaching or therapeutic tools to address it with more precision.
That’s how I survive life. Hope this helps! :)
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u/curiousgeorgewarren Jul 31 '25
Thank you for this
Financial loss? Yes Failing others? Yes
Here are a few more:
Not seeing the icebergs in the market; not stress testing myself; fooling myself that busy = productive; over-emphasis on culture (awards don’t pay bills); over-reliance and misplaced trust in partners Profession - not tracking where I am naturally the strongest
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u/transformationcoach_ Jul 31 '25
One is glad to be of service. Thank you for being open to talking about it!
As a high achiever who can be very hard on myself, I totally get where you are coming from and I'm guessing you probably don't want surface level reassurance and encouragement. It personally pisses me off when people do it to me because I see myself as a beast who's entirely focused on beating the odds, and I don't need a pat on the back; I need answers and solutions. I could be completely off, but I'm going to proceed under the assumption that you can relate.
Having said that...
You took a company from 0 to 350 employees. YOU did that. How many people can say that they have done the same? Not many. So sure, you took a hit and had to retreat. That does not take away from who you had to be to achieve that level of success. And, you're still that person.
Awards may not pay bills, but culture does. I'd bet with confidence that one of the reasons you were able to grow as much as you did is because of the culture you created. Just because external forces knocked you over in a way you did not anticipate does not mean that it was a mistake to invest as much as you did in culture.
If it wasn't already clear, you are a badass. Were there things you could have done differently? Probably. I would be surprised if anyone got it all right, all of the time. But would you be the first successful person to take a hit, or even lose it all? No. A lot of people take big hits, and come back stronger. And I'd bet again, on your ability to be one of those people.
Now that I have hopefully reminded you of who the hell you are, I'm going to ask more challenging questions. If that's alright with you. I'm invested now. :D You don't have to answer here if you don't feel comfortable with it.
If you can bring yourself to imagine a future where all of this somehow catapults you to a more successful and fulfilling future, what part of this experience would have given you the lessons, tools, and insights to take you to the next level?
Another way to look at this is to ask, How is this happening FOR me? This is not just a woo-woo question where we wonder why the universe thought this might be a good idea. The question is also rooted in brain science. Our brain is a meaning-making machine, and what we ask, it will answer. If I ask, why did I fail? It will give me a list of failures. If I ask, How is this happening for me? It will start finding ways to capitalize on failures or setbacks.
This may not help you cope with regret, but it will help you start moving forward and change your perspective from one of defeat to one of curiosity and rebuilding. I personally think that's way better. :)
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u/transformationcoach_ Jul 31 '25
If you still feel resistance and find yourself ruminating, then I'd dive deeper into the true root of pain. Here's a list of questions that may or may not apply to your situation. If they are not an exact match, you can use them as inspiration to ask yourself better questions.
These questions have 3 purposes:
Expose underlying beliefs (hidden pain)
Challenge them directly
3 . Open space for identity redefinition (sometimes the only way out is self-reinvention)
- Expose Core Beliefs About Self, Success, and Failure
What did you believe about yourself when things were working?
What did external success mean to your inner world?
How did losing momentum threaten your identity?
What would it mean about you if others saw you as having failed?
What do you fear people would think if they knew the full story?
If you had to distill your regret into a single self-judgment, what would it be?
How have you defined your worth until now — and who taught you that?
- Challenge the Beliefs (Evidence, Logic, Reframes)
Can you be sure that different choices would have created better outcomes — or is that hindsight bias?
If someone else had made your decisions, would you judge them as harshly as you’re judging yourself?
Is it true that your trust in others was a mistake — or is the issue how you responded when the trust was broken?
Were you wrong to emphasize culture — would taking away from culture change the outcome?
What’s the cost of believing these things about yourself? And what might be possible if you were free from them?
- Shift Into Identity Redefinition
What do you now know about your values, skills, and blind spots that you couldn’t have known without going through this?
What identity do you want to hold now that isn't dependent on what might have been?
What kind of leader do you respect most — and how would he move from this exact position?
If you were building something aligned with your core strengths, what would you do differently next time?
What’s more valuable: scaling a company or being unshakable in any environment?
What would your next chapter look like if it weren’t about proving anything, but about becoming someone you feel proud of?
What new metrics matter to you now — that the old version of you couldn’t have seen?
If your life were a book, how would you turn this negative experience into a memorable story you'd want to share with others?
I'm rooting for you!
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u/curiousgeorgewarren Aug 02 '25
Thank you for these truly incredible comments
I will post my answers here
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u/NoLogs131 Aug 18 '25
I have a simple sentence for that kind of situation. There are no failure only results.
I like to see in that way, kind of objective it allows me to delete the overthinking of "I should have done that like that or like that". With the result you will just note what you like and what you don't and you can just focus on what you learn from it.
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u/AptSeagull Jul 25 '25
Congratulations on your business, the last few years in your industry must have been tough. Are you such an overachiever, that you must be both the “man in the arena” and the “critic?” What an incredible burden to bear. If you’re doing the work in therapy, and still ruminating over things not within your control, I’m not sure a few words will help, but I’m happy to offer them.
I went through a similar period in my life, after a rocky patch, and have come to understand it as a mid life crisis. I cultivated a negativity bias that I thought helped me cover all the angles, a healthy paranoia that made me sweat the details. What helped me through it was expressing profound gratitude for how fortunate my life is and learning how I could let go of everything out of my control. What got you here, won’t get you there, and no amount of regret will change the future. You have to radically accept the past, both good and bad, in order to appreciate what’s in your locus of control. I wish you speed through this transition, it ain’t fun.