Asking for what you want

The first step towards getting the things you want is simply to ask for them. I feel like it has taken me a ridiculously long time to learn this seemingly simple piece of advice. I have heard it a million different ways from a million different sources, but it is only in the past couple years that the idea has truly started to sink in and take hold for me. Of course, asking is not the only step in getting what we want, but it is certainly a good place to start.

Unfortunately, many of us never even take that first step because we are so afraid or convinced the answer will be “no” that we think it’s pointless to even try. If we don’t ask, we never have to face the disappointment of being let down. Then, when we don’t get what we want, it’s easy to say we were right all along and we knew we were going to fail, which reinforces the action (or inaction) of never trying in the first place. It’s a vicious cycle and it needs to stop!

Here’s the thing: when you ask for something you really want, it is always possible that the answer will be “no”. And the more we want it, the more difficult it will be to hear that “no”. But it is also totally possible that the answer will be “yes”, or even something nebulous like “not yet” or “maybe” or “let’s wait and see”. There are so many possible options other than “no” that it’s almost silly to expect that is the only answer you will receive.

(On a side note, I shouldn’t even have to say that there are obviously a few cases where anything other than a “heck yes!” should actually be taken as a “no”, such as asking someone to have sex with you, but that is a conversation for another time. Let’s just all agree that in this blog post, we are talking only about things that are ok to continue asking for until you get the answer you want to hear. Alright, moving on…)

In addition, it is completely up to you how you respond to the answer you get. Maybe all that is necessary is for you to change how you are asking, or to do a little more research and return with a better proposal, or to ask a different person the same question. Some people hear “no” one time and decide that idea is now done forever and it is hopeless to continue trying. For others, being turned down only invigorates them to try harder next time, to continue pushing and learning and improving so that they are more likely to get a “heck yes!” in the future. Whatever the outcome, it is totally your decision.

Knowing what you want

I suppose I lied when I said the first step to getting what you want is asking. Really, the first step is actually knowing what you want! It sounds easy, but sometimes this is really the hardest part. Not only is it important to know what we want in order to get it, we have to be really, truly honest with ourselves about what that is. I have often tried to convince myself that I don’t actually want the things I crave, because deep down I’m afraid I will never be able to get them and it’s easier to just pretend they are not true desires.

It takes a lot of courage to be truly honest with ourselves about what we want and to ask for it, but the stakes are so incredibly high, it is essential that we do this. If you live your whole life denying yourself what you truly want because you are too afraid to even try, you will be cheating yourself of an awesome, fulfilling existence. We only get one shot here on Earth folks and each one of us is entirely responsible for creating the best life we possibly can for ourselves. Nobody else is responsible for your happiness.

I have made the mistake of not asking in countless areas of my life, only to realize later that I might actually have gotten a “yes” if I had only had the courage to be honest about what I really wanted, and I’m betting a lot of you have, too. And I have also sometimes asked for something even when I was sure I would be rejected, only to be pleasantly surprised by the outcome! We never know what another person is thinking unless we ask; this includes our friends, family, coworkers, bosses, partners, etc.

Unfortunately, this is a problem that tends to plague women much more than it does men. As Sheryl Sandberg states in her book “Lean In”: “We hold ourselves back in ways both big and small, by lacking self-confidence, by not raising our hands, and by pulling back when we should be leaning in.” Women are much less likely to put their ideas forward, raise their hands to answer a question, ask for a raise, and all sorts of other actions that come much more easily to men. This affects us both in our work and personal lives. It starts early in childhood when girls who are demanding are labeled as “bossy”, whereas boys who exhibit the exact same qualities are encouraged and seen as leaders. Girls are meant to be sweet, likeable, and agreeable, which does not translate well to being clear about what you want and asking for it.

Fortunately, this is a skill that can be cultivated, it simply takes practice. The next time you have an urge to ask for something, or to do something you really want to do, but there is a voice in your head holding you back, try to examine what that voice is saying. Is it coming from a place of fear, and is that fear realistic? What will be the worst possible outcome if you do ask for what you want? Odds are the world is not going to explode into a million tiny pieces, unless your question is “Can I please push this red button that says ‘detonate stockpile of WMDs’”. Generally, when I compare the worst and best possible outcomes, I realize that I have a lot more to gain from trying than I have to lose.

Fear of Failure

Inspirational posters of kittens climbing mountains love to encourage you by asking: “What would you do if you knew you could not fail?” I am not a huge fan of this saying. The problem is that failure is always an option and we can try to fool ourselves into thinking it’s not, but deep down we know the possibility is there. Besides, if we really did live in a magical universe where we couldn’t fail, then what would be the point in even trying? The rush of succeeding at something you’ve worked really hard for comes precisely because you could have failed, and maybe you already have failed many times before!

Elizabeth Gilbert nails it on the head in her book “Big Magic” when she says: “I think the fiercest question of all is this one: What would you do even if you knew that you might very well fail?” BINGO! It’s a subtle but important distinction. It is not the possibility of failure that keeps us from trying new or scary things, it is the fear of failure itself. It is viewing failure as a terrible thing that somehow marks us as a bad person or will ruin our lives. But the truth is this: it is ok to fail, and most of us will probably fail at many things in our lives. It is not the failing itself, but how we deal with that failure that defines us.

Here is a great example of something I have failed at multiple times before sticking with it: writing a blog. Maybe failed is too strong a word, but I have started several blogs over the years with the intention of continuing to write long-term, only to get distracted by something shiny a week or two later and completely forget about them. But I kept starting over each time I traveled and something about Olive Abroad finally stuck with me.

Elizabeth Gilbert, being the wise lady she is, also wrote this: “Find the thing you love so much, you’d do it even if you failed at it.” I love writing and I love having conversations about topics that really matter to me and that is why I have been able to write 5-page posts almost every single week since I started Olive Abroad. I may never make any money with this blog or have more than 30 readers who are mostly friends and family, but I already count it as a success because I love doing it so much and because it offers me an awesome creative outlet and space to reflect.

What will others think?

There are so many reasons we don’t ask for what we want, and I think a lot of them are more complicated than simply being afraid of hearing “no”. Sometimes maybe what we want isn’t a “yes” or “no” question we have to ask directly, but a more subtle form of permission we are asking for from ourselves or those around us. Maybe we really want to dance at a silent disco in the park but we are afraid we will look silly so we tell ourselves “no, don’t do that, other people will think you are SO SILLY”. When we hold ourselves back in this way, it almost always comes from a place of fear, usually a fear of how we will be perceived by others. What if they think what I want is stupid? What if they laugh at me for even asking? What if they judge me?

For example, I have a pretty specific diet and often have to ask for things to be left out or made differently so I can eat them. Not only am I vegan and gluten-free, I also can’t have peanuts and I find it SO PAINFUL to eat spicy foods. But sometimes I am afraid to ask for multiple substitutions because I don’t want to be seen as a picky eater. Or something comes out wrong but I don’t want to send it back because I feel bad and I hate being “that person” who is always asking for something to be specially made. So I will suffer through a meal that makes me feel sick or doesn’t taste good, which is totally unnecessary! I’m pretty sure that most of the time, the waiter couldn’t care less what I order and it would probably only take the cooks a small amount of extra effort to make a meal I will really enjoy. But I am afraid to ask because of what I think others are going to think about me, which is usually not even true. I have gotten much better about this over the years, but it is definitely still a struggle sometimes and I have to remind myself that it is ok to ask for food that works for me!

The law of attraction

There are all sorts of books out there that talk about the Law of Attraction and I certainly think this idea has some value. While I haven’t totally bought into the whole “visualize a parking space and it will magically appear” sentiment from books like “The Secret”, I do think there is huge value in focusing your energy toward manifesting the things you want in your life. I mean really, it just makes sense. If you spend a lot of time and energy visualizing what you want, thinking about ways to get it, and talking to friends about it, you’re going to start noticing opportunities to make those things happen.

So in the spirit of manifesting the things I want, I will share with you some of my deepest, strongest desires and I will admit to both you and myself that these are things I truly crave and want in life. Saying them out loud is scary because it makes the desires real and that opens up the possibility that they won’t come true, but let’s be honest, those desires are real whether I admit to them or not. And I believe that speaking about them and sharing them can only make them more likely to happen, as long as I am willing to be persistent and continue putting in the effort to manifest them for myself. As the great Jim Carrey said in his commencement speech at MUM (which I will never stop referencing in this blog): “as far as I can tell, it’s just about letting the universe know what you want and working toward it while letting go of how it might come to pass.”

So here you go Universe – I’ve got some pretty specific requests but I’m pretty sure if we work together we can make them happen.

I want to find meaningful work that allows me to be creative and work with people. I want work that is flexible and allows me to travel and create my own schedule.

I want to live in a community of friends who share similar values and who love to play music and dance and have drum circles under the full moon. I want to share a big piece of land somewhere near the city, where we grow lots of our own food and raise our children together.

I want to be financially secure and to feel like I always have enough money to do the things that are really important to me.

I want a handsome romantic partner who is willing to grow and learn with me, who thinks I’m the most awesome person in the world, who plays a musical instrument and loves to dance. I want a partner who is fun to travel with, who laughs a lot and loves his family, and who wants to live in a big community, too.

I want to continue traveling as long as I live and to never stop learning and meeting new people and seeing new places, while at the same time continuing to water my roots in Portland with the community and family I have and love here.

I want Olive Abroad to be something I can share with lots of people all over the world, something that will spark meaningful conversations and encourage others to travel and try new things and love themselves and their lives.

I want to live an amazing, fun, meaningful, exciting, long, authentic, fulfilling life and constantly be surrounded by people I love, who love me back. I want to get the most I possibly can out of this brief existence, to use my time wisely and to enjoy every moment.

Now, is that so much to ask?


What do you want that you are afraid to ask for? What are your deepest, strongest desires that you never dare to say out loud? What would you do even if you knew you could fail?