Why you should start asking for more perks today (and how to get started)
Do you ever have those moments when you know your experience could be better but the idea taking the extra steps to go from good to great just sounds like a lot?
I’m pretty confident you do because this is such a universal experience.
And the reality is that you’re right - going from good to great is more effort. But the key thing to understand is it’s not more effort forever. In many situations there are steps you can take that are more effort up front but pay enormous dividends for your life to be more relaxing, luxurious, ease-filled and fun, if you’re willing to do the things upfront.
Imagine going from…
Spending 2 hours on a Thursday doing the tedious work of reviewing the data for the weekly report and missing happy hour with your coworkers to sipping an glass of Pinot Grigio in the sunshine, hearing about Sarah’s hilarious run-in with the girl in HR
Nibbling on a dried out ham and cheese sandwich that you paid 12.95 for at Hudson News while waiting out your layover to saying yes to the complimentary specialty cocktail being passed around in the Delta lounge while you watch the planes on the tarmac out the floor to ceiling windows
Wearing a 4 year old Jcrew sweater with a hold forming in the elbow to a gorgeous camel Jenni Kayne cashmere sweater that makes you feel like Diane Keaton Coastal Grandmother heaven (and you have in two other colors in your closet)
Feeling phantom vibrations on your phone that you’re hoping are a text from the guy you’ve been chatting with even though he’s been silent for 48 hours to waking up from a nap on the couch to a text that says “hey babe, I’m on my way home but I want to take you out to dinner tonight. Get dressed in something fun and I’ll see ya soon 😚”
All of these are possible.
Which is why I want to dive into why everybody should be asking for more perks in their life and how to get started.
How to get more free stuff, build your confidence and make your life more convenient all with one simple tweak to your conversations
Let’s be clear, does access to an airport lounge, a free drink or a little extra support radically change your life? No, not on their own. But the pure volume of these things that are available is often far beyond the scope that you might realize.
And there’s a key element of inertia - if you are in the habit of not asking, of accepting the okay option, you will do that in big and small ways. On the other hand, if you are in the habit of having nicer experiences, upgrades, and having things work out for you, you continue to take the actions towards having those things and in a way they become more attainable (because if you realize that it’s not that hard to get a yes, it makes it easier and easier to make that ask and to make bigger and bigger asks).
But before we get into all that, let’s start by exploring the possibilities that are available to you right friggin’ now.
There are probably more perks and benefits available than you even realize.
Obviously this is a huge topic. And I am by no means am claiming that this is a comprehensive list. But to set the stage, here is a selection of perks, upgrades, benefits that are available to everybody:
better seats on airplanes
having heavy things delivered and assembled rather than doing it yourself
having your apartment/home cleaned for you
random flowers on a Tuesday
getting upgraded to a better room at the hotel you’re staying at
free alterations
the table with the view of sunset
somebody to do the tedious task at work for you
working remotely
not having to cook for yourself
a reservation at the hot new restaurant that everybody else has to stay up until 12am to book
extra time in the steam room
being able to go to accupuncture in the middle of the day
getting to fly your friend with you for free
a longer massage
more vacation days
waking up to the coffee already made
And I could keep going.
Notice it’s not just about getting free stuff. When I think of perks and upgrades, it’s really anything that improves my life for roughly the same (or less) effort. That can be:
getting something for free
getting something better for the same price
having something done without having to do it myself
Because all these things come back to the ultimate luxury - having more freedom to direct time, effort or money toward the things we want to. And this stacks up over time. At the beginning, just having an extra $20 to be able to have dinner delivered rather than walking to go pick it up can feel like a luxury. The luxury in it is to have the time to squeeze in a 20 min yoga class after you finish work for the day and before you sit down to eat. But at a different point in your life, having the extra cash flow (because you’d figured out how to make more money for the same amount of work) to buy yourself a cashmere sweater over wool and feel like a million bucks showing up to Christmas with your family would feel like the real upgrade. At another point, the upgrade might be taking care of your health but not spending any more time shopping or cooking.
Versions of this go on and on and they will always be intensely personal.
Who you are, your desired life and where you are now all directly influence the things that feel luxurious to you.
But whatever they are for you, one of the most common stories I hear from clients is: “I didn’t even realize that was an option.” Until they saw an example of somebody in their career path making 2x the industry average or until they saw someone at their age traveling first class or until they saw somoene who actually is able to have a slow morning and enjoy their coffee but still be seen as successful at work, they didn’t see it as an option for themselves.
I’m here to tell you that literally anything you want - your biggest most Pinterest-worthy dream travel, wardrobe, routine, sleep schedule - is possible for you but it will not magically fall into your lap. Which is why…
The most necessary step to getting them is ASKING
There’s a super common belief that the ultimate, ultimate luxury is getting the things you want in life without even having to ask. The hotel concierge knows that you like a lake view when you check in and upgrade you to the room with the balcony over the lake without you even having to request it. And I agree that it has a special charm to being taken care of in that way.
But the misconception is that this situation happening didn’t require you to ask.
It did, just way way before that. Because the first time you stayed in that hotel, you probably had to ask for the upgrade. In order for you to be upgraded on the 5th visit, you put the effort in on the 1st and maybe 2nd time you were there.
This is what I was referring to at the start of this article…
Often to get the best things in our life, we have to do something a little harder upfront to then yield the benefits again and again after this.
For my people pleasers out there, the act of asking for something not necessary but that would make their experience pleasurable hits up against many of their fears and not wanting to be seen as greedy or too much. We’ll dive more into those things in a bit. But if this at all resonates with you, I want you to reflect on the woman who has that Pinterest-worthy dream life you desire, who it seems like just has all these great things drop into her lap - the man who surprises her with flowers, the invitation to the beachside party, the boss that doesn’t mind if she signs off at 3pm on Friday - but I would bet that somewhere along the way, she communicated her desires in a way that might feel uncomfortable to you right now but made this life possible.
Asking doesn’t always sound like “can you give me something for free?” It can also sound like:
Asking for explanations - “I’m trying to make the best use of this membership, can you walk me through the benefits I should be taking advantage of?”
Declining something that isn’t a fit for you by explaining what you want instead - “No, I’m not available to meet for a walk - I prefer to have first dates over drinks or a meal.”
Asking for advice - “I’m struggling to get my work done in the office because the frequent interruptions get in the way of my ability to focus. If you were in my shoes, what would you do to make sure you were able to excel in this role?”
The reality is that when we are asking for a benefit, perk or upgrade, we’re also giving something.
You’re giving them a happy customer. A great performance review. The satisfaction of knowing they are making their partner happy. More money in the future because of your customer loyalty.
If you are constantly the one giving advice to friends or taking care of your little sister then you understand that giving something to somebody else can feel really good. It’s not always a pain or an imposition to make somebody else happier.
Now your job is to believe that about allowing other people to make you happy!
So why don’t most people don’t ask for what they want?
When we think about it in the abstract, it can be so easy to understand - oh, yes I should ask for what I want. The worst thing that could happen is I get a “no.”
And yet so many of us don’t go through with asking for the things we want in life. Why? Because the reasons are emotional, not logical.
There are 6 reasons why people don’t ask for what they want:
They don’t know that the option exists (or is available to them)
They don’t know how to ask
They’re scared to be told no
They’re scared of what other people will think about them if they ask for it (and if they get it)
They’re don’t think they deserve to have it
So let’s do a quick dive into what you can do if each of these is holding you back from going after what you want….
They don’t know that the option exists
You can’t go after something you don’t know exists. So what do you do about that? This is where the role of inspiration comes in. It’s absolutely beneficial for you to have people in your view that are further along than you are in a journey or have more of the life that you’d aspire to have.
Paying attention to how they travel, how they take care of their bodies, their routines, their relationships can open up awareness to a whole world of ways that things can be better if you are open to their existence.
This is the healthy version of envy - you are likely going to feel first “omg I want that.” This can easily spiral into “ugh, but I don’t have it.” But if you can stay focused and orient your attention to “what is different about the logistics of their life that allows them to have that?” or even better “what actions would I need to take in order to have that too” you can learn valuable information about how to have it for yourself.
They don’t know that option is available to them
“Oh yeah, she can have that, but I can’t.”
Does that thought sound familiar? Anybody who has struggled with feeling “not enough” or “too much” will naturally err toward thoughts like this when in moments of comparison. I cannot tell you the number of conversations I’ve had with Private Coaching clients when we’ve done exercises like these and when asked: “Why do you think Amelia always ends up with such great guys and you don’t?” and the immediate answer is about what is better about Amelia than the client or the thing that’s lacking or wrong about them that is the reason that she doesn’t have that thing.
But the reality is that most of the time, we CAN have that thing if we are able to act differently or shift the way we feel about ourselves.
This is where the deeper mindset, confidence and self-worth work comes in. You want to identify the stories you’re telling yourself about the reason that you’re not good enough, worthy or deserving and get clear on where they come from. Once you’re clear on your stories, your job is to start arguing with those patterns. Look for the logical errors or the examples in the real world that are counter to the assumption.
John got the promotion over you because he’s a outspoken. Okay, that’s a story. Can you find examples of the quiet, introverted person getting the promotion so you can show your brain that actually quiet people like you can be promoted.
And repeat until you start to believe that you actually CAN have what you want.
They don’t know how to ask
Okay so you know that you can get that upgrade or have the perk, that it’s possible. But the next common reason I hear is that they don’t know how to make the actual ask.
This one is the most practical and the answer is to seek out resources that can give you examples and show you how. Websites like Going and The Points Guy provide a huge volume of resources about travel programs and credit benefits.
Get resourceful, ask questions. There’s always a way.
They’re scared to be told no
Every time you ask for something, there’s the possibility that you’ll be told no. And I can guarantee if you start pursuing more of these perks and benefits and flexibility in your life, you will absolutely get some no’s along the way.
But we have to address it when that fear stops you from asking in the first place.
If you are the type of person who is scared to ask for something because you might be told no, you probably have a story you’re telling yourself about the probability of a yes vs. a no. Because if you believed that it was generally likely that you’re going to get a yes, it’s not that scary to ask. Of course this can vary based on the situation but think about something so simple like asking for extra veggies on your Chipotle Burrito bowl. You know it’s generally accepted for them to do it, so it’s likely you’ll get a yes, so you’re not stressing about asking the question.
The times that we’re scared of the no tells us something about our perceived probability of getting a no.
But most of the time we’re wrong. If you’re scared of getting a no, I can guarantee that the negativity bias that’s natural in humans, the part of our biology where we’re wired to pay attention more to the negative things than the positive, means that far and away we overestimate the probability of a bad outcome and underestimate the probability of a good outcome. And on top of that, the same system means that we overestimate the pain associated with the bad outcome and underestimate the pleasure associated with the good outcome.
Our biology is deeply biasing you to not ask for things because it makes failure scarier and the benefit sound less valuable all to try to keep you safe.
But ironically, this system that is working to try to save you from the potential pain of disappointment is guaranteeing the disappointment because there’s basically a 100% probability of a “no” if you don’t ask.
So how do you address the fear of being told no? It’s simple… practice.
Practice self-talking how well you can manage if if you do get a no, how it won’t be a huge deal AND go out there and actually ask questions and get told no and practice supporting yourself through whatever comes up in those moments.
Very quickly you’ll begin to see that it’s not as hard as you expected and that you don’t get as many no’s as you expect.
They’re scared of what other people will think about them if they ask for it (and/or if they get it)
Especially my people pleasers out there will resonate with this one. Often we are so held back by the opinions of others that we don’t go after what we want for ourselves.
What if they think I’m needy? What if they think I’m being difficult? What if they don’t want to keep dating me? What if they judge me for wanting nice things?
We can twist ourselves up in knots. But at the end of the day, they might. We do not control the thoughts of others so there is a real possibility that they might have those thoughts you’re so scared of.
Your decision is whether you’re going to let the possibility of somebody having a thought stop you from living the life that you want.
My best trick if you’re in this pattern - Imagine yourself 10 years from now. You have the thing you’re considering asking for and you have for years. Imagine the shift in the trajectory of your life, whether it’s how your body looks because you healed your hormones by managing your stress, which started with this little ask or you had extra time by delegating that annoying task at work and now are in a much more senior role with higher pay. Play the story out for yourself of the compound impact of the ask if you were to get what you wanted. Now ask yourself - will that 10 years from now version of me be bothered by this person thinking that of me?
If the answer is yes, then maybe it’s not the right decision to make the ask - if it would have that meaningful a negative impact on your relationship, it’s okay not to ask.
But if not, then the decision you’re making today is to deny yourself that 10 years from now reality for this person. Is it worth it?
They’re don’t think they deserve to have it
And ultimately, this is the deepest and most serious fear that comes up and can be at the root of many of the above. You might worry about what your family will think of you flying first class because deep down you’re not sure you deserve to treat yourself like that.
You might be hesitant to ask the guy you’re seeing to give you more physical affection because deep down you’re struggling with your own beliefs about how worthy you are of a great guy to truly love you.
This deep rewiring work is powerful because when you heal those deepest beliefs about yourself, you are going to wipe away many of the other fears that might come up around deserving what you want.
If you want something in this life, it is because on some level you know you are capable of having it. It’s just a truth of the world. I don’t spend my days dreaming about being born in 1500 or living on Neptune because it’s not available to me. The things that we feel drawn to even if they feel decades and millions of dollars far away still on some level signal that our brain knows it’s an option for us.
You might have some deep inner work to do to get there. But you can get there.
Why you should start asking for more stuff today
Part of why I’m so passionate about you asking for the small things in life - the Comfort+ upgrade, a free drink, an extra 20 minutes - even though they’re not radically transformational is because of the practice.
You’re not going to be devastated if you don’t get the upgraded seat so it’s the perfect opportunity to normalize the feeling of being told no. You can help your body see that the world doesn’t end and you can handle it.
Getting to the place where you can make these asks and have it not feel like a big deal, will allow you to then build the muscle memory on other bigger asks and possibility for no’s.
You will also help shift that biased perception in your brain about how often you get yes’s vs. no’s. This in turn will motivate you to ask for more things because you’ll feel more confident.
But you also get a much larger benefit.
When people decide it’s better to just accept their life as it is, the “good not great” version, there’s always this deeper knowing that they didn’t go after the big dream, that they’re “settling” for what is because to get the premium version requires more work, which in turn hurts their view of themselves.
When you settle for “good not great,” you signal to yourself that you’re good not great. And that good is all that you deserve.
On the other hand, you have the power in your actions to signal to yourself day in and day out that you are clear on what you want and you believe that you are worthy of having it (just by the action of going for it). You don’t even have to succeed all the time - just the act of trying does the job.
So if you’re convinced that you want to get better at asking for what you want, let’s find some places you can start today to cultivate this skill!
5 favorite easy places you should ask for more perks and free stuff in the next week
Asking for the table I want at a restaurant even if the one they offer me is fine
Call your credit card company and ask them to lower my APR or increase your credit limit (about 50% of the time they’re able to bump up my credit limit which helps my credit score)
Ask someone to help me get my carry on down from the overhead bin - I’m fully capable of doing it myself but it’s nice to not have to and often it’s easier for them and no skin off their back (especially if they’re a tall man)
Ask a sales associate at the store if there’s any discounts they could give you on the purchase, just cause! Every once and a while, they’ll just throw on a 10% discount just cause you’ve been nice
Ask if the restaurant is willing to give me a half glass of wine when I don’t want a whole other round but I’d like a little top off. Many times they’re happy to only give me a half glass but just as many times, they’ll just top me off for free
You can try one of the above or come up with your own - then DM me on Instagram to tell me what you did and how it went! I cannot wait to hear the amazing bonuses and perks you are going to secure for yourself just by beginning to ask.
