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Index/Finance/Business Finances Through the Lens of Your Natural Strenghts
Business Finances Through the Lens of Your Natural Strenghts artwork

307. Don't Let the Bully Steal Your Truth (prevent future regret)

Business Finances Through the Lens of Your Natural Strenghts · 2026-03-16 · 17 min

0:00--:--

Key moments - from our scoring

Substance score

18 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality4 / 20
Guest Caliber2 / 20
Specificity & Evidence3 / 20
Conversational Craft3 / 20

Conny Graaf explores how fear of future regret paralyzes business owners and individuals facing major financial decisions - whether selling a house, making a hire, or pivoting a business direction. The core insight: regret is a pattern, not tied to the outcome. A $500,000 house sale triggers the same internal "bully" voice as $600,000 would. Graaf introduces the concept of "having your own back," inspired by coaches Brooke Castillo and Stacy Beaman, which means deciding in advance to defend yourself as fiercely as you'd defend a loved one who made a tough call. She challenges listeners to calculate the full cost of indecision - not just financial dollars, but time wealth, energy wealth, and integrity wealth (referencing her framework from episode 301). The practical solution: document your decision-making process, reasoning, and values before the bully voice emerges later. This approach builds unshakable self-trust and prevents future regret from rewriting past truth. Essential for entrepreneurs struggling with decision paralysis, perfectionism, or a pattern of second-guessing themselves.

Key takeaways

  • →The cost of indecision extends beyond money to time wealth, energy wealth, and integrity wealth, making it critical to evaluate the full cost of not deciding, not just the cost of deciding.
  • →Future regret about decisions is a pattern rooted in self-judgment, not the actual financial outcome, so no amount of money will satisfy someone with a tendency to beat themselves up over past choices.
  • →Building self-trust happens after a decision through how you treat yourself afterward, specifically by committing in advance to defend yourself like you would defend someone you love, regardless of the outcome.
  • →Documenting your decision-making process in writing or voice memo creates a record you can return to when doubt arises, allowing you to remember your reasoning and shut down the inner critic.
  • →Confidence on the outside emerges from having self-trust on the inside, and this self-trust is built through consistently having your own back rather than joining the inner bully in self-recrimination.

In this episode

  1. 1The Fear of Future Regret in Decision Making
  2. 2Recognizing Regret as a Pattern, Not a Money Problem
  3. 3Calculating the Full Cost: Time, Energy, and Integrity Wealth
  4. 4Having Your Own Back: Building Unshakable Self-Trust
  5. 5Practical Implementation: Documenting Decisions for Future Self

Mentioned

Brooke CastilloStacy BeamanMichael SingerKonigraaf

Topics in this episode

Brooke CastilloDecision-making under uncertaintyFuture regret pattern recognitionTime wealthEnergy wealthIntegrity wealthSelf-trust buildingStacy BeamanMichael SingerThe three types of wealthFear of future regretThree types of wealth (time, energy, integrity)Self-trust and decision-makingDecision documentationInner bully voiceThe cost of indecisionHaving your own backEpisode 301 (referenced)

Questions this episode answers

How do you stop second-guessing financial decisions like selling a house?

Document your decision-making process in advance - your thoughts, feelings, options considered, and what mattered to you beyond money (time, energy, peace of mind). When doubt arises later, reviewing this record confirms you were clear and grounded when you decided, silencing the regret voice.

What does 'having your own back' mean in business decision-making?

It means deciding in advance that you will defend yourself like you'd defend a loved one, regardless of the outcome. You commit to not abandoning the version of you who made that call, which is how self-trust actually gets built - not before the decision, but through how you treat yourself afterward.

Why does increasing the sale price not eliminate regret if you have a regret pattern?

Regret is a pattern, not a financial outcome. If you tend to beat yourself up over decisions, the internal bully will find reasons to criticize any choice - whether you sold for $500,000 or $600,000 - because the issue isn't the money; it's the belief system driving the self-judgment.

What costs of indecision should you consider beyond money?

Conny identifies three types of wealth: time wealth (life on hold while waiting), energy wealth (mental load of open decisions, circling thoughts, uncertainty), and integrity wealth (peace of mind, sleep, mood, and how your stuck state affects those around you).

How does having your own back build self-trust and confidence?

Self-trust grows through how you think about your decision afterward and treat yourself post-decision. Confidence is what happens externally when self-trust happens internally. By defending your past decisions, you prove to yourself you're trustworthy, which compounds over time.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

The episode offers one mildly non-obvious reframe - that regret is a behavioural pattern independent of price outcome - but the bulk of the runtime is padding, repetition, and generic self-help coaching language that any B2B operator will have encountered. The practical tip (document decisions) is reasonable but thin.

Whether you sold your house for 500,000, 550,000 or 600,000, that inner bully voice...It will show up regardless of the sale price. Why? Because it's not really about the money. It is a pattern.
What is the cost of not deciding? What opportunities will I miss while waiting for something else?

Originality

4 / 20

The central framework is explicitly credited to Brooke Castillo ('make a decision and then have your own back') and reinforced by another coach, Stacy Beaman - so the episode is openly a retelling of borrowed ideas. The 'three types of wealth' concept is merely referenced to another episode rather than developed here.

Years ago, I heard my coach, Brooke Castillo, say something that changed my inner dialogue.
Recently, Stacy Beaman reminded me in an email with the same idea.

Guest Caliber

2 / 20

This is a solo monologue episode with no guests whatsoever. The host draws on anecdotes from one unnamed client and borrowed frameworks from named coaches but never features a practitioner with demonstrated B2B operational experience.

Well, hello my friend. I'm your host, konigraaf.
A recent call with one of my clients, she presented me with a scenario similar like that.

Specificity & Evidence

3 / 20

The only numbers in the episode are illustrative and hypothetical (a house selling for $500k - $600k). There are no real case studies, named companies, measurable business outcomes, or cited research - just an unnamed client anecdote and vague references to past episodes.

Whether you sold your house for 500,000, 550,000 or 600,000
In the three types of wealth that I talked about in episode 301, a few weeks

Conversational Craft

3 / 20

The episode is an uninterrupted solo monologue with no interviewing, no follow-up questions, no productive tension, and significant repetition of the same points across the 17 minutes. The structure meanders rather than builds, and there is no mechanism to challenge or deepen any claim made.

So here is what I said to her, my client, and this is really the heart of today's episode.
Okay, my friend, I would love to hear from you and what you think about having your own back.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

decision43back19offer13cost11money10wealth8decisions7price7making6future6house6feeling6real6past6bully6trust6

Episode notes

I talk quite a bit about how to make good decisions here on the podcast, but what about what happens after? That quiet voice that shows up months later whispering "you should have waited, you left money on the table, you got it wrong."_ Or maybe the voice isn't whispering but yelling? In this episode I talk about something that drives so many of our decisions without us even realizing it, the fear of future regret. And more importantly, what to do about it or how to prevent it. It's practical, honest, and maybe a little bit mind blowing, at least that's how it was for me when I first heard the solution. From Chaos to Peace Consulting Inc - Get my newsletter In Your Element delivered every Moon-Day (Monday) Schedule a FREE " Bring Your Chaos To Me" Call Take the free Quiz and figure out your >>> Organizing Personality

Full transcript

17 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Well, hello my friend. I'm your host, konigraaf. Thank you so much for allowing me back into your ears today. I want to talk about decision making again, but a little bit different than before. Also about something that drives so many of our decisions, either as business owners, but also in our private life. But we might not always be aware of it, or if we are aware of it, we might not dare to say it out loud. I'm actually talking about the fear of future regret. That specific sneaky thought. What if I look back a year from now or six months from now or whatever and feel like I made the wrong decision? Let's take an example. Let's say you're facing a big financial decision like selling your house. This is a decision where it's objectively there is no right answer, right? The market could go up, the market can go down, nobody knows. But we still have to make a decision. We still said we want to sell our house and so we will have to accept an offer or not accept an offer. And we need to define some rules around when we do accept an offer and when we don't. But here is what can happen. You can get an offer and it's a fair offer, let's say. And instead of feeling really relieved that there is actually an offer on the table and that you can work from here on the deal, you find yourself circling the same thoughts over and over and over. What if I look back a year from now and feel like I left money on the table, I made the wrong decision, I jumped too quickly. You're worried that your future, you will be judging you down the road. And that feels very real and is feeling also threatening. And it keeps you paralyzed and not wanting to make a decision or stalling your decision, right? So a recent call with one of my clients, she presented me with a scenario similar like that. And she was quite emotional around it. Not just because of this big scary decision, but also because after talking this through with her, she realized something about herself. She realized and recognized that she has a tendency toward regretting her decision, toward second guessing herself. So it's a tendency to always look back and wonder, what if I would have decided different? What if I would have waited? What if I would have acted quicker? And Michael Singer says to this, this is really fruitless and useless because you can't change the past. So you're really tormenting yourself with something that you can't even change anymore. So it's of no use. And here still we are doing it and me included, right? So Now, I'm m not saying just other people are doing this. I do this too. But I have learned over the years to do it less. Let's just say like that. So here is what I said to her, my client, and this is really the heart of today's episode. The message I want you to hear specifically, if you want, if you need to make a money decision, I want to say to if you have a natural tendency towards regretting your decisions or towards beating yourself up over past decisions, if that is your pattern, then no price or no amount of money will ever feel high enough or will ever prevent that. Because the tendency toward regret doesn't go away just because the number is bigger. So think about it this way, again with the house example. Whether you sold your house for 500,000, 550,000 or 600,000, that inner bully voice, the one that screams at you, you should have waited. You should have known better. You left money on the table. It will show up regardless of the sale price. Why? Because it's not really about the money. It is a pattern. Now hold that thought that it is a pattern. Because here is what I also want to offer you. What I see a lot is that people only look at half of the equation when they make decisions like this. They ask, what is the risk of accepting an offer, let's say the offer for the house. What if I leave money on the table? But they rarely ask, what is the cost of not deciding? What opportunities will I miss while waiting for something else? What is this uncertainty doing to me right now, to my feelings, to my nervous system, to my sleep, my mood, my mindset? How long am I willing to put my life on hold for a maybe to stay in this indecision, in this waiting spot? What is the version of me that keeps waiting costing the people around me? How am I acting towards these people? What do these people have to, um, experience around me, with me in this limbo space? And also, what does staying stuck in this indecision says about how much I trust myself and my decision making. And very important, when I say what does it cost me? Again, I don't just mean financially. I mean in the three types of wealth that I talked about in episode 301, a few weeks. Time, wealth, energy, uh, wealth and integrity. Wealth. Every m. Day, week or month, you wait for a better offer or a better moment or a better feeling. What is that really costing you? It could cost you time, wealth, time you could be spending on the next chapter of your life, the next thing, the next life. That is Waiting on the other side of this decision, it could cost you energy, wealth. The mental load of an open decision is enormous, especially if it's such a big decision. The circling thought, the what ifs, the what, watching the market, the hoping, the dreading, that is all not free. It might be free, like you don't have to pay dollars, but nevertheless, it is very expensive. And it can also cost you integrity, wealth too. Because at some point you have to ask yourself, I'm not making a decision in the hopes of more dollars. But what? At what. But at what price? At the price of my peace of mind, at the price of my energy, at the price of my sleep and my mood. And what about the people around me, my partner, my kids and my friends who live with the version of me that's stuck in this limbo? What is it costing me? What is the real cost? And that real cost rarely shows up on a spreadsheet. On a spreadsheet. So the real question really isn't just how do I get enough money? The real question is, what is the full cost of this decision? And what is the full cost of not making the decision? Now, let's go back to what I said earlier about the future. Regret is not about the money. It's a pattern. I want to offer you a solution for this pattern. Years ago, I heard my coach, Brooke Castillo, say something that changed my inner dialogue. And recently, Stacy Beaman reminded me in an email with the same idea. This idea, when I first heard it, was mind blowing to me. But since then, it has helped me so much to not beat myself up for decisions I made in the past. So here is what Brooke and what Stacy both are. Make a decision and then have your own back, no matter what. I know that sounds simpler than it is in reality. Still, think about what it means for a moment. Most of us are very good at defending the people we love. If your best friend or your child made a tough decision with the best information they had at, uh, the time, and six months later someone was beating them up over it, you would defend them like a mother bear, Like a mother bear defends their cub, you would say, she did the best she could with what she knew at the time, you would assure her too, that she's made a good call. But we rarely do that for ourselves. We give the bully free rein. We often even join in beating ourselves up. And that's what my client was worried about. And that's why she didn't want to make a decision, or that's why she was paralyzed. Making A decision or that's why it was so hard for her to make a decision. She knew she had to make one, she knew she wanted to make one, but she was struggling. So having your having your own back means deciding in advance that you will be that good friend to yourself, that no matter what the outcome, you will not abandon the version of you that made the that call. And this is also how and where self trust gets built. It's not before the decision, it's after it. Specifically how you think about your decision afterwards and in how you treat yourself after the decision. And this is why I said to you earlier that a big important question is what does staying stuck in this decision say about how much I trust myself? Because if you have your own back, if you decide in advance that you will have your own back, you can trust your decision. And this is also why Stacy said something that really landed for me as well. And it's around confidence. She says confidence is what happens on the outside when self trust is happening on the inside. Now, as you know, I don't just want to talk about things in abstract ways. I always want to offer you a practical thing or way in how to implement what I'm suggesting. So here's the practical thing I recommended to my client. And that's the same thing I want to offer you too. For whatever decision, big or small, what you're sitting with right now, you can do the right. When you make the decision, write down all your thoughts and your feelings, what you are doing and why, why you decided the way you did, what options you have looked at and compared the pros and the cons, what mattered to you and what and what doesn't. And again, not just about money, it's also about time and energy and the peace of mind. You write it all down for the future you for when that bully in her head shows up six, nine or 12 months from now and tries to yell at her for making the decision the way she made it. Because like I said earlier, if you have the tendency to beat yourself up over past decisions, then it doesn't matter if you sold at, ah, the highest price possible or not. If you made decision A or decision B, the bully will always find the reason why the decision was flawed and beat you up for it. Now, in your case, it might not be about the sale of a house, of course, or an investment you decide on. Maybe it's about a hire you made for your team, a client you took on or didn't take on, or a client you let go, or a pivot you took in your business, right? It really doesn't matter what decision. When you have that voice show up, you want something to be to fall back onto. And by that time you might have forgotten how you felt exactly and what your thinking was exactly. And that's why writing notes or even a voice memo to yourself will take you back back and will also confirm that you were very clear and grounded when you made the decision. And this will shut up the bully. You want to be able to go back and say, I was there, I made the decision on purpose with the information I had for reasons that were real and true to me at the time. And I'm not going to let a, uh, future feeling or thought or a bully in my head erase my past truth. And this is what having your own back looks like. Not to be confused with blind optimism in yourself or pretending it was easy, or pretending it's the right thing, or trying to ignore the nagging feeling and the nagging loud voice in your head. That's not working. It's standing by yourself the way you would stand by someone you love. So this is what I want you to take away from this week's episode. Before you decide, ask yourself the full question. Not just what does this cost me in dollars? But also what does waiting cost me in time and in energy and in peace of mind? There is more to wealth than money. If you need a refresher, you can go and listen again to episode 301. And then when you make the decision, also document the decision and have your own back the whole way through. So before I end, I want to say you deserve to be defended by the person who knows you best. And that person is you. So next time you make a big decision, or any decision, really, try being your own mother bear, document it, stand by it, and refuse to let a future feeling or thought rewrite a past truth. That is what having your own back looks like. And over time, that is how you build unshakable self trust. Okay, my friend, I would love to hear from you and what you think about having your own back. For me, that was a very new and surprising concept when uh, I first heard it and it has really changed the way I treat myself, the way I think about myself, but also the way I make decisions. If this is, um, a new concept for you, like it was for me, or even if it's not, I really would like to hear from you and I would love to hear your thoughts. If you get my weekly emails in your element, just hit reply on one of them and tell me what decision that you are having your own back on right now. And if you're not signed up for my in your element yet, well, first of all, what the heck, you're really missing out. But you can also find me on Instagram at I amconigraph and you can send me a dm. Um there and tell me what decision are you having your own back on right now? Okay, my friend, thanks for listening all the way to the end. It truly means a lot to me. Have a beautiful week. Take good care. Talk to you next time. Bye for now.

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