Managing Expectations

Life Tools + Systems + Mental Models

How the skill of managing expectations is one of the most critical to living a good life, and is currently one of your biggest obstacles


Expectations have a powerful impact on our emotional and mental headspace. The gap between expectations and reality is an overwhelmingly common source of all our woes. We see this personally, socially, and professionally.

Personally, we start hobbies we don’t actually have interest in. We fill bookshelves with books we don’t actually want to read. We order meal kits from start-ups championing misshapen produce or being ready in two minutes or less. Easily tantalized by convenience and possible best-case outcomes, we do things that bring us immediate satisfaction and then on the backend we always have a tinge of buyer’s remorse. Expected fantasies bring potential elation, and reality struggles to meet those expectations, making even good decisions feel shitty sometimes.

Socially, we see this with our friends, our purchasing decisions, and even with total strangers! Poorly communicated plans for a night out? I guess we’re ending up at that dive bar that one person lives at, but others always question how they end up there. Everyone in your friend group is buying barrel aged stouts or a bougie wine collection? Guess what you’re going to have littered across your apartment, peeking out from every conceivable storage space. Everybody on Instagram showing you their perfectly toned tummies while on holiday in the Maldives? Well not you, you’re just some idiot that goes to work every day because clearly you did something wrong. This plays out again, and again, and again.

Professionally, this is almost a requirement in consulting, and I’m certain many of you have experienced it too. Someone on the team is habitually late to meetings even though the calendar invite is out there days in advance. A sales team member makes promises to potential clients to ensure the deal closes, leaving the delivery team with the uncomfortable task of either explaining why that can’t be done, or trying to figure it out before the curtain is pulled back to expose the truth behind the great and powerful delivery team. The way our bosses execute and communicate with the team often leaves us feeling undervalued, and the company values advertised on the recruiting website rarely show up in the office.

These moments of missed expectations show up every single day, repeatedly. They wear us out, make us feel disillusioned, and can even stop us from taking action that could materially improve our lives. The gap between what we expect and what happens, between what we want and what is, can warp our perception of the world around is. It causes us to lose focus on exclusively what we can control, and to temper our mind to that malleable piece of life. When we focus our expectations and actions on what we can control and just experience and analyze the rest of life as it comes, we create a suit of armor for ourselves. We enable ourselves to navigate life with more intention and resilience.


Under Promise, Over Deliver

Throughout my consulting career, the best consultants I have worked with have all said one thing – under promise and over deliver. It is one of the single greatest pieces of professional advice I have encountered. I manifest it as much as possible. And, it is the most succinct, accurate creed to remind yourself the importance and practice of managing expectations. Ironically, despite the constant humming of this phrase in my head, I continue to see it intentionally ignored in life and in business.

The resulting events of these slights are so predictable, it’s hard not to laugh when they happen.1 Because the reality is, when a sale is at risk or there is an opportunity to increase our social value through signaling, this advice is remarkably unattractive. You can’t be the hero if you announce the risk on the project and refuse the foundational consulting model of ‘figuring it out’. You can’t be the excel modeling whiz if you ask for a couple extra days to turn it around. And so, the disregard for managing expectations becomes the source of friction. The external friction of meeting deadlines and expectations that often don’t make sense, and the internal friction from the avoidable positions we put ourselves in.

Our expectations drive our experience. They’re why we get frustrated when we feel those closest to us don’t reciprocate our thoughtfulness or love. And why we cyclically suffer buyer’s remorse once we’re holding that great new piece of tech and realize it didn’t magically make us feel better. Or why when we hype up in our head for weeks and finally get to that Michelin starred restaurant, three bites of endangered nigiri and a morsel of dehydrated of watermelon don’t hit quite as right as a big slice of Artichoke pizza.

It’s the balance between vanity and identity. Between potentially damaging a professional relationship and integrity. Between swiping the credit card for something fleeting and building an identity around a lasting idea. It’s the difference between signaling and being who we really are and who we want to be.

We seek grandeur and ostentation to escape mediocrity, but when intended reality doesn’t align to manifested reality, we’re let down.

In the exact same way, our unrealistic expectations about our personal experiences muddy our perception of reality. It’s easy to envision yourself standing on a stage in front of thousands of people or watching a book climb the bestseller list or drying the ocean water off your perfect six pack. You know what’s not as fun to imagine? Sitting alone in a studio, or at a desk, or in the gym, sailing through the emotional tidal waves of self-doubt, creative block, and imposter syndrome – repeatedly. Showing up each day to be vulnerable to do the work never knowing if it will pay off to anything. That’s managing expectations. Chasing something you genuinely, passionately believe in. Doing so with an open mind and honest intentions. And doing it knowing no outcomes are promised.

Tom Segura, one of the best active stand-up comics in the world 2, feels so strongly about the concept of managing expectations he carved out time for it in his Netflix special, ‘Ball Hog’. Conceptually, anyone can appreciate the grueling nature of the stand-up industry. Making almost no money when you first start, yet still having to give public performances, scraping by, and driving all over to various nightclub gigs to get your reps in, refining your set based on killing it or absolutely bombing (again – publicly and typically for no money), and then you get up and do it all again. That is the reality for all stand-ups, and is certainly not the piece of being a professional comedian the average person would fantasize about. Knowing that it may never pay off, but you have to put the work in because it’s important to you? That’s managing expectations.

In ‘Ball Hog’, Segura calls out managing expectations as one of the most valuable skillsets you can develop and encourages people to follow their passions in their life. And that honing this skill and mindset is the tool that will ensure anyone will still derive fulfillment even if their goals are not traditionally successful.

“I’m a dream encourager…I want you to have crazy dreams. I’m serious. I really do. I’ll give you the best advice, sincerely, not a joke, that I ever got about pursuing a dream…As long as you accept that your dream might not go exactly as you plan, you will still be fulfilled by the pursuit of your dream. So always go after whatever you want to do. Otherwise, what’s the point in living, right?”

That’s the power of managing expectations.


System of a Professional

With that perspective, what’s something we can tangibly do effectively practice managing expectations? We can change our approach to our self-chosen “most important” activities; transitioning from an amateur system to a professional one.

Systems end up indicating and facilitating the success of our endeavors. James Clear covers this masterfully in his book Atomic Habits. The mechanisms which we knowingly build and follow, which facilitate replication and consistency, are what allow for the progress to compound and, one day, become something great. They’re what allow us to do the work regardless of what a new day might bring. We will all feel lost. We will all feel confused and scared. I haven’t met or read about a person I respect who hasn’t experienced imposter syndrome. In these moments of vulnerability, we need mechanisms to allow us to show up anyway.

“We don’t rise to the level of our expectations, we fall to the level of our training.” 3

Our need for things to be immediate or easy (ideally both), is supported by a betrayal of our expectations. The desire for things to be different but not respecting the process it will take to get there. Not showing up to just do the work.

On recent episode of The Knowledge Project, Seth Godin outlines the difference between being a professional and being an amateur. He draws this distinction to show the stark gap between a hobbyist and someone excelling in their field. Amateurs don’t have schedules and deadlines, professionals do. Amateurs don’t have to be vulnerable and fail publicly, professionals do. Amateurs don’t have to show up to do the work, professionals do. Professionals show and up and honor their commitments, and show up and do the work, regardless of how they are feeling. That comparison is illuminating on a fundamental difference between performance and meandering. Between success and failure. Not everyone who shows up every day is successful, but everyone who is successful shows up every day.

When we expect things to be easy or completed quickly, we are easily discouraged. Flipside of that same coin, when we don’t expect things to be challenging and time consuming – and when this skews our perception of our real goals and aspirations – we are likely to visualize quitting as soon as we start.

If there is a shortlist of lessons on how to take a truly honest and vulnerable attempt at achieving your goals –at living a life you choose – managing expectations is near the top.

Godin details how valuable the concept of getting yourself in the right mindset and physical space to create and show up every day is – something James Clear heavily stresses by discussing environment design and creation. Things like showing up daily, having a playlist or uniform that signals to you it’s time to work, setting your gym clothes out the night before, or having a workflow you follow to get into a rhythm – these are the activities that work up to building a system. And the effort put into consciously designing and executing systems, rules, and mental models all circle back to our deliberately calibrated expectations of our goals and of our corresponding actions.


Recalibrate to the Journey

People who expect to show up do the work will find fulfillment. They are significantly more likely to find success. People who expect to be successful will often struggle to be consistent and abandon their goals.

Missed expectations are that gap between what you anticipated or desired and what you actually experienced. The space between the goal and the actual work to get there. It feels bad to have missed expectations. And that feeling of failure, weakness, and futility is what causes us to fail and abandon our goals. Failure is inevitable, abandonment is the path of least resistance. And the narrative around these goals reinforces the choice of abandonment.

Focus on the journey. This is where all the time will be spent anyway. Even if you achieve your goal of say writing a book or having $100k in the bank or having washboard abs – all the actual time is spent writing alone, reviewing your personal finance strategies, and in the gym. The goal is just another milestone on a never-ending journey.

If all you focus on is your end goal, you can be quickly overwhelmed and disoriented. You need to focus on all the smaller goals, systems, and processes that build into that goal. Expect the dirty, unglamorous work to get there. Hope for good outcomes and work feverishly as though they may never come. Plan to do what is required so that you can one day enjoy what’s uncommon. Then you can start to do the work and build a path toward who you want to be. When you’re faced with a monolith in front of you that you need to move to achieve your goals, what can you really do? Do you push on it, in futility, trying to change the reality of what it is? Or do you simply pick up a pickaxe and start swinging to break it down piece by piece? 4

Time will pass no matter what we do. Recalibrating to the journey of our lives can drastically change how we execute on our goals and treat ourselves. It allows us to begin playing the long-term game, and a game that we can better define. The long-term game cares about you showing up and doing the work. Games of glory and shortcuts care about grandeur and luck. The long-term game cares about the trends of your life – did you show up more times than you skipped: this week, this month, this year? The short-term game yields fleeting results and limited fulfillment because of our missed expectations.

The long-term game lets us work toward our true identity and potential. It lets us experience the power of compounding our smaller actions we take each day. And it lets us rewrite the narrative of what a worthwhile, quality output looks like. It allows us to set challenging but encouraging expectations for ourselves. Commitments of focus and elbow grease, not assumptions of unique talent and genius.

Be true to yourself and accept that it may not be a great success, or it may not go exactly how you expected, and that’s ok. Do the work, define what’s needed to accomplish whatever your goal is, or whoever you want to be.  Do it ferociously and honestly. The greatest fear I have in my life is that I will look back and regret inaction and fear of failure. And that my fears and insecurities held be back from living a life I would have been proud of. Also, insects. All of them.

When you’re 90 years old, looking back on your life, what will you think of what you did and how you lived? 5

See you soon,



Life Tool / Strategy: Managing your own expectations.

Key Concept(s): One of the biggest obstacles in life is the gap between what we expect to happen and what happens.

Actionable Insight: When taking action and setting goals, managing your own expectations is a skill like anything else, and it can be trained over time. If we focus more on the journey and consistently putting forth our best, honest effort, we are likely still to feel fulfilled regardless of the outcomes.


1 – As a career consultant, this is called “getting staffed on project” and “executing a project plan”; everyone I have ever worked with is still working through the data on being totally transparent and completing a project in a reasonable timeframe, charging a fair price, and finding a client that is open to the concept.

2 – I think any rational, tempered person would say this is an opinion / obviously subjective. I am not one of those people.

3 – Quote from Archilochus which James Clear adapted for Atomic Habits

4 – Partially inspired by the abundance of stories in The Obstacle Is The Way by Ryan Holiday

5 – Decision by Design from Shane Parrish / Farnam Street

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