How to Make Clear, Conscious Decisions

Picture this: You're sitting in your home office at 2 AM, staring at a term sheet that could change everything.

The offer is $100 million for your company. It's real money from a serious buyer, and you have 48 hours to decide.

But your gut tells you the company is worth $150 million. Maybe more.

You've spent seven years building this. Seven years of 80-hour weeks, missed family dinners, and sleepless nights just like this one. Your spreadsheet says take the money–bird in the hand, right? Your heart says hold out–you've earned every dollar of that extra $50 million.

Your mind races between worst-case scenarios: "What if this is the only offer we get?" versus "What if I'm leaving $50 million on the table?"

Maybe your situation is different, but the feeling is the same.

Paralyzed when everything depends on ‘getting it right.’

I get calls about decisions like this more often than you'd think. Founders paralyzed by choices that could define their entire future, unable to sleep, unable to think clearly when they need it most.

But here's what I've learned coaching hundreds of founders through these high-stakes moments about how to make great decisions, especially when everything is on the line...

The Real Problem Isn't the Data – It's Your Context

Most founders think high-stakes decision-making is about analyzing content–the data, valuations, market timing, and pros and cons.

Content doesn't determine your decision quality. Context does.

Content = the facts, circumstances, and data about your situation

Context = the lens through which you view and interpret those facts

Whether you're facing an acquisition offer, considering firing a co-founder, deciding to pivot your product, or choosing between funding rounds–the decision isn't really about the external circumstances.

It's about the unconscious beliefs and emotional state driving how you process the choice.

But knowing that context matters is just the beginning. The question becomes: how do you actually shift your context when fear takes over?

Why Some Decisions Feel Hard

You make hundreds of choices daily without thinking–what to wear, what to eat, which emails to answer first.

So what's the difference between an easy choice and an agonizing decision?

Fear.

Decisions that feel hard are decisions that we have fear around.

Most of us make choices specifically to avoid certain feelings–regret, disappointment, fear, shame, guilt, or the terror of being wrong.

This is exactly what creates those sleepless nights staring at big decisions.

We go into our head and spin and spin trying to figure out the right answer that will lead to the outcome our mind is certain is the “good” one and will ensure we only feel the feelings we want to feel.

But what if you didn’t need to avoid any of your feelings? What if instead of needing to figure out the right answer, you ask yourself what you really want to do?

This is where your body becomes your most reliable guide.

Your Body's Built-In Decision Compass

Before making any important choice, pause and notice: Does this option make your body feel expansive or contracted? Particularly pay attention to the space around your heart and to your belly.

Following your authentic path creates expansion – you feel bigger, more open, alive, relaxed into possibility. Fear-based thinking creates contraction – your body tightens, you feel smaller, less energized.

Your body is constantly processing information and sending you signals about what's aligned versus what's driven by old patterns or limiting beliefs.

When a client asks me about making a major decision, I invite them to feel into both options. "When you imagine saying yes, what happens in your body? When you imagine saying no, what shifts?"

This physical awareness gives you data your thinking mind often misses.

The Nuance Most People Miss

Here's a key distinction I see many founders struggle with:

How do you discern whether a choice feels authentic for you when it also scares you?

Sometimes you'll feel fear toward the decision that feels most expansive. You might feel excited about starting that new venture but terrified of the risk. You might feel energized by the thought of firing that toxic team member but scared of the confrontation.

Just because you're scared doesn't automatically mean you should do it. And just because you're scared doesn't mean you shouldn't.

The key is distinguishing between fear that arises from patterns (coming from old stories and limiting beliefs) and fear that arises from presence (informing you of something to pay attention to).

Your edge is the place where you let fear stop you from being fully authentic.

So if you authentically want something that scares you, go for it!

The 90-Second Rule

According to the Conscious Leadership Group, emotions last for less than 90 seconds if you just allow yourself to feel them. If they continue after that, it's because we've gotten hooked by a story in our mind and resisted feeling the emotion.

Instead of resisting difficult feelings around your decision, feel them fully for 90 seconds:

• Feel the terror of walking away from that big offer
• Feel the regret of potentially selling too low
• Feel the shame of admitting your initial strategy was wrong

On the other side is clarity about what you really want.

The Feel-First Approach

When you drop your resistance and welcome your fear, you get clear about what you really, authentically want. You start to be guided by what 'feels right' instead of spinning in your mind trying to figure out the right answer.

There’s an Art of Accomplishment podcast entitled Feel over Figure that explains this beautifully.

Most founders try to think their way to the right answer. But the clearest decisions come from feeling first, then choosing.

Before any significant choice, try this:

1. Check if you're above or below the line - Are you constricted, reactive, or feeling like you need to control things you can’t control? If so, pause. Your decision-making capacity is compromised when operating from fear.
2. Feel the fear instead of avoiding it - Whatever emotion you're trying to avoid by making this choice, feel it fully for 90 seconds. Don't resist it–let it move through you.
3. Notice what feels expansive vs. contractive - Does each option make your body feel bigger and more open, or tighter and smaller? The expansion points toward what wants to be created.
4. Trust what feels right - Once you've felt the fear and checked your body, what authentically feels right to you? This is your inner wisdom speaking.

Putting It All Together

Learning to be guided by what feels right – tuning into what you authentically want – is a better way to guide your company than trying to figure out the right thing to do.

Feel the fear of firing that underperforming exec, then have the conversation. Feel the uncertainty about your product direction, then decide whether to pivot. Feel the vulnerability of asking for help, then reach out to that advisor.

This approach gives you access to your authentic wisdom rather than getting stuck in analysis paralysis.

Your most aligned choice is waiting on the other side of whatever fear is creating the struggle.

Remember: The goal isn't perfect decisions. It's conscious decisions made from clarity, authenticity, and alignment with your deeper vision.

With love,

- Dave Kashen

P.S. If you want to develop your ability to make clear and conscious decisions, I'm hosting a free workshop on June 25th that will guide you through the most powerful frameworks for leading from clarity instead of fear. Register here for the free Zoom workshop (June 25th, 4-5:30pm PT).