How to gain confidence in making great decisions?

Ever wish you had a crystal ball to make decisions easier?

Spoiler: We all do!

We’ve all been there — staring at a decision, paralyzed by the fear of making the wrong move.

In those moments, it’s easy to forget that not deciding is often the worst choice of all.

And I've quoted Teddy Roosevelt 100+ times by now:

Why does it matter?

• Indecision keeps us stuck while fear keeps growing

• Even the most accomplished individuals second-guess themselves

• Decision-making is a skill & it requires practice and conscious effort to develop

I've worked with many clients who are incredibly successful, yet struggle with decision-making.

Whether it’s the fear of making the wrong choice or dwelling on past decisions, the anxiety is real.

And it's something we work on together because being decisive is crucial for high performance.

That’s why I felt compelled to write a newsletter on how to build confidence in your decision-making.

I’ve had this conversation too many times with clients, which is why today I’m peeling back the curtain to share with you my take on:

• Why it’s hard to make decisions

• How to build a system to be more decisive

• What really matters when you’re at a crossroads

Want to gain more confidence making decisions?

Keep reading.

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Before we begin: Here’s what you might have missed in the past few weeks…

• In issue #54 of The Productivist, I shared how & why you should take control of your emotions. Access it here.

• In issue #53, you learnt my high performance tips for boosting your confidence. Check it out here.

• In issue #52, you discovered how to receive, ask for and give productive feedback. Read it here.

Which one was your favourite? Just hit reply and let me know! 🫶

Big idea #1: Why is it so hard to make decisions?

It’s not because you’re bad at making them.

In fact, most of the decisions you’ve made so far have likely been good ones.

So, what’s the real issue?

You haven’t embraced being a good decision-maker as part of your identity.

Think about it:

• When you make a good choice → you often just move on & forget about it.

• But when you make a tough or less-than-ideal choice → you dwell on it.

  “I should have done this differently. I’m terrible at making decisions.”

This habit reinforces the idea that making decisions is hard.

Here’s the truth:

• You’ve been making great decisions all along.

• You’ve been turning tough situations into something positive.

• You’re just not giving yourself credit for it.

So, what’s the narrative you’re telling yourself about your ability to make decisions?

And more importantly, how can you change it?

One powerful way is through reflection.

Remember the concept of a confidence bank account?

Open one just for your good decisions, especially the ones where you made the best out of a tough situation.

Every choice — big or small — goes into it:

• Decided to exercise today. →  I made a great decision!

• Said NO to a project that you know will drain you. →  I made a great decision!

• Despite things not going as planned, you chose to enjoy your day. →  I made a great decision!

Just like big achievements are the result of consistent small actions…

Great decisions are built on the foundation of these small, confident choices.

Big idea #2: Have a framework

Want to boost your confidence in making decisions?

Start with a proven framework.

The good news is there are countless decision-making frameworks you can try:

• Cynefin Framework

• RAPID Framework

• WRAP Framework

• OODA Loop

• The 5 Why’s Method

• And many more

But before diving into any of these, there’s one key question you should always ask yourself:

• How much time and research do I need to invest in making this decision?

To answer that, consider Jeff Bezos’s concept of Type 1 and Type 2 decisions.

If making a decision is like walking through a door:

Type 1 decisions are one-way doors → irreversible.

• These require careful thought and effort.

• Consider the decision from different angles and prepare thoroughly.

• Think about the broader impact on others and related factors.

Type 2 decisions are two-way doors → reversible.

• These can be made with incomplete information.

• Act quickly, test the outcome, and adjust if necessary.

• Aim for a good decision, but also consider time, effort, and cost.

Most decisions fall into the Type 2 category, meaning they don’t require elaborate frameworks.

But if you’re facing a Type 1 decision — an irreversible one — you might want to choose the right framework to ensure you make the most informed choice possible.

As you gather information, keep these guidelines in mind:

1. Be clear on your objective.

2. Seek understanding, not just knowledge.

3. Focus on best practices, not outliers.

4. Write down your biases and assumptions.

5. Decide how certain you need to be (you’ll never reach 100%).

6. Know the risks of doing nothing.

7. Consider the impact of your decision on others.

Big idea #3: First, a decision is made. Second, that decision is made right.

Every business owner should know, the sales process doesn’t end with the purchase. It begins there.

Once a customer buys, the real work starts: getting them to use, enjoy, and share your product.

This builds momentum and long-term fulfillment in your business.

Similarly, a decision isn’t made when you’re 100% sure it’s the right one.

You make the decision first, then you commit to making it the right one.

In other words:

Often, it’s not about making the right decision — it’s about making a decision, committing to it, and doing everything you can to make it the right one.

Let me explain.

How do you know if a decision is the right one?

In math, there’s a clear right answer.

But life is full of variables, and there’s no single right answer.

You might join an amazing company, only to face layoffs months later.

Did you make a bad decision by switching firms? I don’t think so.

But it might not feel like the right decision either.

This is where the real wisdom comes in:

It’s up to you to make that decision the right one.

• What if it’s not too late to reach out to other employers you were interested in?

• What if you use this time to take a career break and reassess what you truly want?

• What if this is the perfect opportunity to launch that business you’ve always dreamed of?

Remember:

A decision is made right AFTER it’s made, and you are the one who makes it right.

What decision did you think was a bad one, but later turned it into a good one through the choices that followed?

The Productivist Challenge: Stop looking for reasons not to do it

Here’s a simple yet profound truth:

If you’re looking for a reason not to do something, you’ll always find it.

• Thinking about eating healthier?

• Considering working with a coach?

• Thinking about starting your own business?

I can give you 10 reasons NOT to do any of these.

But does that mean you shouldn’t do it?

Of course not!

Because you only need one compelling reason to say YES:

→ It will help you achieve the quality of life you know you want and deserve.

Yet, most of us grab hold of those reasons not to act, even when we know the action would bring us long-term happiness.

Feeling called out?

Good.

It’s time to switch to long-term, compound thinking:

→ Your small actions in the right direction will build into big wins over time.

But on the flip side:

→ Your inactions will compound into feeling stuck, filled with regret, and inadequate.

So, here’s my challenge for you:

Stop looking for reasons NOT to do something when you already have one powerful reason to do it.

And go do it.

Whether you listen to this advice is also a decision. Make a good one. 😉

The Productivist Question:

You don’t learn from experience; you learn from reflecting on that experience.

That’s why I recommend asking yourself these questions, especially after making challenging or important decisions:

• What was the decision-making process I followed, and was it effective?

• What were the key factors and considerations that influenced my choice?

• What worked well in this decision, and what could have been done differently?

Wish you a week full of great decisions ahead,

Valeriya

PS: What decision have you been sitting on for a while now? Let me know by hitting reply or DMing me on LinkedIn!

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