The Sales Rep’s Ultimate Guide to Being More Optimistic

There’s something to be said about the whole “positive thoughts bring positive outcomes” mindset shift these days.

Now don’t get me wrong, some of the stuff out there is just plain mumbo jumbo.

I’ve been trying to “will” a winning lottery ticket my way for years. Still no luck.

But if you’re an optimistic person, you give off a certain aura that people respond to. They seem to feel your enthusiasm, your sunny outlook, your hopes for the future.

And in that same way, people—specifically buyers—can sense your pessimism. They can smell your desperation. And when they do, it’s going to send them running for the hills.

But don’t worry, optimism isn’t a natural-born talent.

And with just a bit of work, you can make the mindset shift away from pessimism and toward optimism too.

That’s why today we’re asking what is an optimist? What kinds of benefits do optimists enjoy? Why is it so important to be optimistic in sales? And most importantly, how do you become more optimistic?

We’ve got a lot of material to cover here. So let’s jump right in.

What Does Optimistic Mean?

Optimism is an attitude in life that reflects being hopeful and confident about the future. If you’re an optimist, you expect good things to happen. And obstacles aren’t signs that you should turn back, but rather chances to learn and grow.

Pessimists, on the other hand, expect the worst. Their efforts will go unrewarded. Their goals will never be achieved. And the best thing to do in the face of a challenge is to give up because they’re never going to succeed anyway.

Of course, most people aren’t completely one or the other. And in fact, a healthy bit of pessimism can actually keep optimists grounded.

But in general, optimists are healthier, less stressed, more resilient, and more persistent when it comes to achieving their goals.

Positive emotions tend to lead to more positive events and physical health.

Let’s dive a bit deeper into what an optimist looks like.

What Is an Optimist?

An optimist is someone who generally hopes for the best and sees the best in their world. And that optimism might look something like this in the workplace:

  • My morning started out miserable. But instead of letting it ruin the rest of my day, I stayed positive because I believed it could only get better.
  • I lost a client because of a mistake I made. However, I realized what I did wrong and changed my processes so it won’t happen again.
  • I’m behind on my numbers for the month. But rather than getting depressed by this information, I’ve switched up my cadences and increased my prospecting to make up for it.

The funny thing about optimism is that it isn’t necessarily a trait you’re born with. Instead, it’s a choice. And the more you choose to think optimistically, the more you can start seeing the benefits of this worldview.

If you can change the psychology of any negative events that you face into a potential positive future, then even with realistic thinking, nothing can hold you back.

Stats About the Benefits of Optimism

So, how does optimism help anyway?

Below are a few stats to give you an idea about the massive benefits of becoming an optimistic person.

  • The University of Pennsylvania found that optimistic sales professionals outsell their pessimistic counterparts by 56% (HBR).
  • Researchers from Stanford University found that optimists have higher quality and longer-lasting romantic relationships (Verywell Mind).
  • Optimists are 40% more likely to get a promotion over the next year, five times less likely to burn out, and six times more likely to be highly engaged at work (HBR).
  • Optimists tend to have a 15% longer lifespan and a 50% greater chance of living past 85 than pessimists (Heart&Stroke).
  • Optimists save more. One study found that 90% of optimists have put money aside for a major purchase compared to just 70% of pessimists. And two-thirds of optimists have started an emergency fund, while less than half of pessimists have done the same (HBR).

Why Do You Need to Be Optimistic to Win in Sales?

Okay, so optimism is clearly associated with some very clear benefits.

But why does cultivating an optimistic mind matter in sales specifically?

Let’s take a look.

A) Optimism Gets You Going

Let’s be real here. Making it in sales is tough.

The daily grinding to find new prospects, the same old discovery call conversations and demo presentations, the rejection—it’s enough to make some people avoid getting started in the first place.

And truth be told, once you think about how many calls, emails, and messages you have to send to get a single bite, it can be pretty disheartening.

But optimism gives you that extra nudge out the door each day. It’s the little fire burning inside that lets you see the possibility of today being a day for wins. That your efforts very well could pay off.

And if you’re a pessimist, you’ll never want to even get out of bed in the morning.

B) Optimism Keeps You Going

Optimism is great for instigating action. But it’s also the best way to keep moving towards the finish line.

Consider this example:

You’ve been working with a prospect for the past week or so to see if they’re a good fit for your services. Your discovery call went great, and the prospect ticked all the boxes. However, during your demo presentation, the buyer focused on price objections and slowed down the progress of the deal significantly. 

Now, a pessimist might approach this situation by simply dropping the prospect, deciding that they’re not going to be a fit. The deal is dead. And that’s all there is to it.

But an optimist will see the light at the end of the tunnel. They’ll dig a bit deeper to find out if the budget can be reallocated, spread across multiple departments, or use other creative financial solutions.

A pessimist, then, tends to give up more readily. But an optimist is resilient to challenges. And thus, they’re more likely to turn deals around at the first sign of an issue.

C) An Optimistic Mind is a Healthy Mind

Optimism is also healthy. And it all comes down to stress.

Stress is a natural, even helpful emotion in small doses. But when that stress is frequent and intense, it can cause serious health problems.

Jagdish Khubchandani, PhD, is a professor of public health at New Mexico State University. He told Healthline that:

“Too much stress and negative states of mind weaken the neuroendocrine and immune responses of the body, causing vulnerability to disease or weaker recovery from diseases as the body cannot mount a strong response to stress and disease,” he added. “It is a complex interplay of disease/stressor vulnerability, perception of disease/stress, and the reaction of our body to stressors/disease that are interlinked.”

The more optimistic you are, however, the more resilient you become to stress. And that means you can face challenges with a clear mind and find real solutions to the problems you’re facing.

D) It’s Contagious

Finally, having an optimistic outlook is contagious, especially in sales.

The more optimistic you are, the more your buyers will be hopeful about their future when they’re working with you.

Think about this—if you’re constantly complaining about the weather, talking about the terrifying changes in national and international politics, and generally just being a hell of a downer all the time, buyers won’t want to pick up the phone when you call.

But more than that, buyers will be put in a pessimistic mindset when you call. And that will lead them to take fewer risks, close their minds to the prospect of change, and close fewer deals with you.

Take an optimistic bias to talking with prospects, and the opposite will happen. They’ll start focusing on the rewards more than the risks. They’ll be open to exciting new solutions, even if it means changing legacy systems. And they’ll want to work with you to improve their business.

And that can be a powerful way of boosting your sales success.

The Optimistic Sales Rep Framework

Alright, so obviously optimism is great. And in the sales world especially, an optimistic mindset can drive serious increases in successfully closed deals.

But how do you develop a optimism bias? What is an optimist in practice doing to keep that glass-half-full mindset?

What’s great about mindset is that it isn’t set in stone. And with a bit of work, you can learn to become more optimistic by reframing your pessimistic thoughts using The Optimistic Sales Rep Framework:

  1. Recognize Your Thoughts
  2. Ask for Evidence
  3. Ask If There’s Another Point of View
  4. Ask What the Implications Are
  5. Ask If This Pessimistic Thought Has Any Usefulness

Let’s take a closer look at each of these steps.

1) Recognize Your Thoughts

It’s difficult to change things that you don’t realize are happening to you.

That’s why the very first step to cultivating an your positive psychology is stepping back and recognizing negative thoughts when they pop into your head.

We have around 60,000 to 70,000 thoughts a day. And most of those thoughts are automatically created by your subconscious. So in order to change those negative thoughts, you have to first become really good at spotting them.

Now, the difficulty here is of course we tend to be on autopilot.

Sure, we have thoughts that pop into your consciousness from time to time. But for the most part, those thoughts sail by our focused mind without us stopping to examine whether they’re helpful or just pessimistic crap.

And that’s why you’ll need to do a bit of work getting better at observing your thoughts.

Practice Observing Your Thoughts

Becoming aware of your thoughts can end up being the most difficult stage for some.

But there are techniques and strategies you can use to get better at becoming more thought aware.

Mindfulness meditation is one of my favorites. Once you get good at it, observing your thoughts will become much more natural. And that means you’ll be in a better position to change those pessimistic thoughts to optimistic ones.

To practice mindfulness meditation, all you need to do is:

  1. Find a quiet place where you won’t be disturbed.
  2. Sit comfortably and close your eyes.
  3. Focus on your breath as you inhale and exhale.
  4. When a thought enters your mind and breaks your breath focus, acknowledge it, observe it, and let it pass as you shift back to focus on your breath.

What’s great about this meditation is it only takes 5 minutes per day. Seriously, that’s it.

If you can commit to 5 minutes per day, you’ll find yourself starting to become more aware of your thoughts in as little as a week or two. And that’ll make the next step of the framework even easier.

“We think on average 60,000 thoughts a day, we're aware of less than 1% of them. 80% of them are said to be negative. And so stress naturally happens. It's the function of the mind to stress. But what we can do is, we can better handle the stress.” – Interview with Nina Purewal, Best-Selling Author & Founder of Pure Minds

2) Ask for Evidence

If there isn’t any evidence of negative outcomes, then it’d be wise not to believe them.

Seems pretty simple, right?

Well, this stage is all about applying that same logic to your own thoughts.

The most convincing way of disputing a negative belief is to show that it’s factually incorrect. Often when you look for evidence that a negative thought is true, the facts just won’t be on your side.

Pessimistic thoughts that we have tend to come up when we face adversity. These negative thoughts in the face of adversity are usually emotional overreactions to the situation.

But when we look for evidence to support these overreactions, most of the time we’ll find that any evidence is tiny and so the overreaction can be ignored completely.

This step alone will knock away most of your pessimistic thoughts throughout the day.

If evidence alone doesn’t resolve your pessimistic thought, it’s time to move to the next step of the framework and see if there’s an alternative point of view.

Adopt a Logical Eye

At this stage of the framework, it’s important to approach the thought from a logical stance. And it’s important not to get too caught up in the emotions connected to the thought.

See, a lot of our first impressions are driven by emotion. And there’s a real evolutionary benefit to assessing a situation emotionally first before jumping into logic.

Acting on emotion is fast, and a lot of the time, it happens without us realizing it. But logic is a bit slower. And that lost time assessing a situation logically could mean life and death.

So if we were in the wild and saw a rustle in a bush, it’s in our best interest to be startled and run off. That rustle could be a predator ready to attack. And if we didn’t have that startle response and instead investigated the situation using only logic, we likely wouldn’t have enough time to avoid becoming a lion’s dinner.

But in this framework, you need to make sure you aren’t just reacting to your thoughts emotionally. And instead, you’re looking at them from a logical, rational perspective.

“Let's say that you walk outside and you see like a garden hose and then your heart starts to beat really, really fast. So, that's the pre-processing part, but then when you actually step back for half a second and you actually identify that as only this a hose rather than a snake, then that delay in terms of the interaction shows you the flow of information that travels from the primal brain into the logical brain.” – Interview with Felix Cao, Neuromarketing Expert, Growth Strategist, & Founder of Happy Buying Brain

3) Ask If There’s Another Point of View

The next step of the framework is to look at your pessimistic thought and ask, “Is there another perspective to this thought?”

No two humans are the exact same. We all have different abilities, tendencies, experiences, and thoughts. And that means no two people will have the same point of view on what’s possible.

Beyond that, most events have many variables, so you can look at any thought or event with a bunch of different points of view.

For instance, if you did poorly with a customer, it could be that they were having a bad day. Or maybe you caught them at the wrong time, or your vocal tonality was just slightly off. It could be you were still thinking about the previous call where you were rejected. Or perhaps they may have just bought your product from someone else.

There are usually limitless ways of looking at a potential issue.

Pessimists have a way of latching onto the worst of all the plausible causes. But when you look at the different points of view for your situation, you might find a perspective that is much less drastic.

You might even be able to find an optimistic point of view where you’ve just been given a // great opportunity.

Cultivate a Mindset of Openness

Now you may be thinking, “But Will, how do I come at issues from a different point of view if I don’t see any others?”

Well, that’s where openness comes in. The more open you are to learning about the perspectives of others, the more different views of actions, events, and the world at large you’ll have to draw on.

Openness is actually one of the “Big Five” personality traits that many social psychologists believe determine personality type.

Individuals with high openness are willing to try new things, entertain foreign ideas, and dive into unfamiliar experiences. And as a result, they tend to be more creative, flexible, and adventurous.

In terms of our framework, cultivating a more open mindset will let you see your own pessimistic thoughts from a different perspective.

“We can't understand the experience of others that is so far outside of our own experience. So talking to people who have different experiences is going to give us different perspectives. So that you can go from, I don't know, what I don't know. To, I know what I don't know, so that I can get to, I know what I know.” – Interview with Michele Molitor, Coach, Hypnotherapist, & Imposter Syndrome Expert

4) Ask What the Implications Are

“It’s no use crying over spilled milk.”

We’ve all heard the saying before. Simply put, the phrase means it’s not worth worrying about things that will have little consequence.

Believe it or not, worrying in situations like these spends an enormous amount of energy. And as a result, optimists have a distinct advantage over pessimists here because their finite mental energy each day isn’t getting drained by useless activities. So, they have more mental energy left at the end of the day to compete longer or harder.

And sometimes the facts or the different points of view of a situation won’t all be positive.

Occasionally, the negative thought that you had might actually be correct.  In this scenario, we need to reduce the impact of the negative belief by asking…

“Even if the belief is correct, what are the real-world implications?”

Oftentimes the belief can be true. But if nobody else cares, why should you beat yourself up over it?

How will this affect your performance? Are there any problems you see arising because of this situation? Who stands to be hurt by it?

In many cases, you’ll be surprised to find that the results of this negative thought should it occur aren’t as far-reaching as you think.

Take Solutions into Account

If you’re having trouble getting around the negative implications of a thought or situation, start looking at the solutions.

For example, maybe you do suck at cold calling right now…

This may be true. But with just a little bit of effort, it could change entirely. For instance, you could simply take a class to learn how to get better. You could download proven frameworks for cold calling cadences. You could follow time-tested templates. And in no time, you could get better at cold calling.

So why worry about the negative thought when you know that you can flip the evidence that supports it on its head with a little bit of training?

See how examining the solutions can make even the most negative implications seem meaningless?

If eliminating the possible negative implications from your pessimistic thought doesn’t work, it’s time to bring out the big guns and ask yourself how useful the thought is. Let's cover that in the final step of this framework.

“Do not worry about failing or being rejected because it is going to happen. But it is also going to happen that you will succeed.” – Interview with Samuel D. Osborne, Educator & Author

5) Ask If This Pessimistic Thought Has Any Usefulness

We all do things that turn out to be a waste of our time.

For instance, if you know ahead of time the effect of each of your daily selling efforts (e.g., 1 prospect out of 100 cold outreach touches), you’d probably not bother with half of them.

The same rules apply to pessimistic thoughts. If you have a pessimistic thought, and you don’t think it’s useful to be spending energy on it right now, then you really have to question if you should just drop it.

Sometimes the consequence of holding a negative thought matters more than the truth of the thought itself.

If your thought is destructive, even if it is true, it might serve you better to be ignorant and forget about it.

Tough pill to swallow, I know. But learning to let go can actually be one of the most valuable qualities you can have in this line of work.

I’ll never be the best-looking sales trainer out there with this big nose… I don’t care ????. I can be ignorant of it, live a happier life, and not suffer the consequences of doing so. And that means I can move on.

You can do the same too.

Realize That Letting Go Takes Practice

This won’t be easy at first. But if you’ve run your pessimistic thought through every other stage of the framework, you’re better off doing so.

However, that’s going to take practice. Think of it like a muscle. The more you work at it, engage with it, the easier it becomes. Eventually letting go of inconsequential negative thoughts will become second nature.

And that will make it 10X easier to shift out of that negative mindset and turn back to what really matters—becoming the best damn sales rep you can be.

“Being positive and being able to recover from negativity and set back at a more rapid pace isn't about insight. Most of us know that we're not serving ourselves when we're completely being hijacked by a bunch of negative emotions. And we've got all this brain chatter and anger and frustration, fear, et cetera. But our ability to actually shift out of that is 80% a muscle response and only 20% an insight response.” – Interview with Adam McGraw, CRO at Positive Intelligence Inc.

Wrapping Up

We all have negative thoughts. It’s only human.

But what separates the most successful sales reps from the least is, in part, their ability to move past these negative thoughts. To reframe them so that they can keep learning. Keep selling. And keep growing as a professional.

And eventually, optimism (and the numerous benefits of it) comes to them as naturally as riding a bike.

You can start cultivating an optimistic mind too with The Optimistic Sales Rep Framework.


  1. Recognize Your Thoughts
  2. Ask for Evidence
  3. Ask If There’s Another Point of View
  4. Ask What the Implications Are
  5. Ask If This Pessimistic Thought Has Any Usefulness

Now remember—this type of mental work isn’t easy. And it takes consistency to be sure. But the more comfortable you get with recognizing your thoughts and questioning their truthfulness and usefulness, the easier and quicker it’ll come to you.

So stop dwelling in the muck and the mud. And start cultivating an optimistic mindset.

Your earning potential, mental health, and future self will thank you for it.

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