Rant about something I just saw at Starbucks (on getting past fake “gatekeepers”)

Originally sent this out as an email- decided to post it here:

So I’m at Starbucks (been here for a few hours), and I’m in Atlanta…which is a music hub..lots of singers and songwriters

And there’s this young singer…maybe 20-21… and another guy who I suppose is his manager.

And the manager wants the kid to sing in Starbucks to get some feedback. So he goes around to the different tables to say “hey, we’re going to sing in a minute, just wanted to let you know.” Then he goes to the counter and he asks the the Starbucks staff if it’s “OK”.

Not even a manager, mind you… just a regular barista. And of course she says “no, you can’t sing in here.”

Why? Is it because she doesn’t like music? Probably not.

It’s because she doesn’t want to get in trouble, do anything out of protocol or do anything that might possibly draw attention to herself. It’s not even about the kid singing. It’s about her.

And I’m thinking to myself two things:

First, the manager shouldn’t have asked for permission to sing. He should have just had the kid do it. People would have most likely broken into applause (we love surprises, flash mobs, etc) – then if the Baristas or managers were still mad…he could have just asked for forgiveness later. Ask for forgiveness…but never ask for permission to demonstrate your worth or power. 99% of the time people will say no because they are scared.

Second, this is a perfect example of how gatekeepers are often underpaid and under qualified to evaluate us. The people who reject book deals, venture funding and movie scripts are usually never the real decision makers. They are usually the interns and low-level employees just filtering through the crap for the boss. Even the bosses are just gatekeepers to the public. These people all have agendas of their own. It’s all about them. It’s never about you. Yet we let rejection from these people make us think that the world is rejecting us.

It’s not. How can the world reject us if it hasn’t even SEEN us?

If we just skip them entirely and find our way to the decision makers, we have much better shots at getting what we want.

So fuck the gatekeepers. How can we figure out ways to get around them and go directly to the source?


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Daniel DiPiazza

Daniel is the founder and CEO of Rich20Something.

A millennial business mastermind, he has successfully started three consecutive freelance businesses and scaled them to over $100K in revenue with zero startup capital. His work is regularly featured in Time Magazine, Fortune, Entrepreneur, Business Insider, Fox News, and Yahoo! Business.

His debut book, Rich20Something, publishes on May 2, 2017.

  • Daniel, love this post. I’ve always felt the same way when it comes to the gatekeepers and what you are “allowed” to do. Screw em. Take the power back!

    • Rich20Something

      Agreed John….and thanks for reading. In their defense, sometimes they don’t even know what they’re doing – so we have to make sure that while they’re still figuring things out, we don’t shy away from sharing our gifts. Happy to have to in the community, man!

  • Kevin Diamond

    Haha great take Daniel and extremely valid. Looking forward to seeking out ways to cut out those middle men and connect directly with the real source!
    “We can’t solve problems by using the same kind of thinking we used when we created them.” A. Einstein

    • Rich20Something

      Kevin Diamond hey Ken, thanks for being part of the community. You’re so right – it’s all about going to the source!

  • ZackHornbuckle

    Why brother with the gate keepers in a situation such as this? This is an area where the boss isn’t around and so I wouldn’t bother to ask at all. As you stated it is much easier to ask forgiveness. If one doesn’t dare to be great then one will have a hard time being successful. Fortune favors the bold.

    • Rich20Something

      ZackHornbuckle Agreed 100% Zack. I think it also comes down to making better decisions as the entrepreneur/performer. Asking yourself “Do I even NEED to ask right now?” and “What are the risk/rewards of just doing it?” Often the risks are actually very minimal – us getting “frowned” at or OMG “kicked out”. In reality, who cares. The benefits of showing our gifts are often much greater.

      Can you name a situation where you had to make a decision between asking a gatekeeper or just going for it, and how did you react?

  • hazelmaepan

    Very spot on. I’ve been ruminating about this for years – lots of talented people yet unrecognized because of these “fake” gatekeepers. And then, some more years later, once these talents get exposure anyway without these gatekeepers’ permission, the public actually likes them and it is these same gatekeepers who then do the chasing. Inspiring post and rings true. Glad to have read this tonight. 😉

    • Rich20Something

      @hazelmaepan Totally agree, and thanks Hazel – welcome to the community 🙂

  • Emil89EC

    Fake gatekeepers are an everyday problem. Some of them succed in getting in your way, some of them fail. Is up to us to see past them and make sure we aren’t distracted by them.
    A very good article about them. I loved the read.

    • Rich20Something

      @Emil89EC Absolutely – I think some of us can also confuse gatekeepers with decision makers, which is a huge mistake! Thank for joining the community, Emil! Happy to have you.

  • Liz Flores

    Hey Daniel,
    Great post! I never thought of someone like a barista as a gatekeeper, but they are. I think were taught for so long that we need to ask for permisison or well get in trouble (school, parents) that after a while its second nature. I remember when I was in grade school, I saw a little girl pee her pants because she had to wait to ask the teacher to go to the bathroom! Just go the bathroom, just do what you need to do, just contact the head honcho. Gate keepers can waste so much time and it can be difficult to find ways to streamline the processes. Really glad I joined the tribe!

    • Kevin Diamond

      Liz Flores So true Liz! great story and reason why this is so injected in our nature!

      • Rich20Something

        Kevin Diamond Liz Flores I just thought about that. Why the heck does somebody have to “ask permission” to use the restroom?

        Did you guys ever have bathroom passes? LOL. Gatekeepers abound.

        • Liz Flores

          Rich20Something Kevin Diamond Liz Flores  Daniel, I went to a very strict grade school lol so no bathroom passes! Some teachers were lenient..this one was not. We had to ask for permission ALL the time.

  • Oliver Armstrong

    This is a great example of a not-always-so-obvious barrier in business and life. I always try to live by an “ask forgiveness not permission” policy. At least then, worst case scenario, you still got to do what you wanted to try even if it didn’t pan out 🙂
    Other fake gatekeepers that come to my mind are: entire HR departments at soul crushing office, and mid-level managers at companies that could use your product/services. Unfortunately these are usually the first points of contact with a company. Like Daniel said, let’s be discourage by the scaredy-pants nay-sayers

    • Oliver Armstrong

      Haha, stupid phone post. Let’s NOT be discouraged!!! 🙂

    • Rich20Something

      Oliver Armstrong Totally, man. Have you ever gotten the feeling that the SOLE purpose of an HR department is to piss you off?

  • Thanks for this post Daniel.
    We’ve all been in this position at some point in our lives!
    There’s no doubt that finding the decision maker is a number one priority when you’re trying to break into a market, land a particular client, or get that link you’ve been trying to secure for months!
    But there’s SO much to be said for taking the initiative!
    As you said, they should have just started singing, who doesn’t like singing after all? You’re going to attract more customers than you’ll loose if this kid was any good.
    Use your logic for crying out loud!

    • Rich20Something

      Sam Barnes For real, man. Can you think of a recent example where you encountered a gatekeeper? What did you do about it?

  • Marshall

    I dig it. At first I kinda thought this was something like what I’ve read before, however the last few lines are what made this unique to me. That’s because I can see how you figured out a way to get directly to the decision makers in your hacking elance post, since you deliberately figured out how to  distinguish yourself from the pack.

    • Rich20Something

      @Marshall Yeah man, it’s all about learning how to differentiate from the herd and not be discouraged by people who tell you know. Because they will. ALL the time.

  • David Mallia

    Hey Daniel! Great story, thanks for sharing 🙂 
    I can’t imagine how disappointed that singer must have felt when she was rebuffed like that by the barista. It’s usually other people’s own psychological blocks that set up the gates for others and like you said, the motivations are typically very selfish: trying to save one’s ass or looking good for the boss. One’s talent shouldn’t be held hostage by other people’s fears (or one’s own)! 
    Imagine if her manager just told her to stand up and belt out her song… she would have gotten the recognition she wanted, Starbucks would have gotten some publicity as well and everyone would have had a good time. When you look at things from a bigger perspective, you’d notice that everybody could have benefited from the event. I think what began as a spontaneous idea by the manager or the singer was held back by the manager’s trepidation. You simply cannot overthink certain things!
    Anyways, great to be here, thanks again! 🙂

    • Rich20Something

      David Mallia Agreed 100% David. When you think about things from the bigger perspective, suddenly many of our fears melt away with the idea that…to be honest, many of the details in life don’t matter all that much. This isn’t to say don’t be diligent…it’s just that many of the bad things we think will happen never do, so we should be taking more calculated risks. Don’t you think?

      What’s a calculated risk you’ve taken recently?

  • Tiffany Lee

    My poor boss is a gatekeeper.  It’s a shame because she is a cool lady but she is such a strict rule-follower.  The other day I needed to leave work early because my kid wasn’t feeling well.  I had to beg for permission to simply WORK FROM HOME!! Seriously?  I could have just walked out but I didn’t want to leave them hanging so I asked if it was okay to continue my work at home while I took care of my kid.  She was hesitant to grant me that much.  I’m over it!  I’ve been doing this crap for 2.5 years – enough is enough.  That insulting amount of change I get every other Friday just isn’t worth it.

    • Rich20Something

      Tiffany Lee And that’s the sad part. Sometimes, the gatekeepers don’t even know what they’re doing….or if they do, they are too petrified to act outside of that role. We can’t let their paralysis become ours. Even if we like them or even (gulp) love them.

  • Chris Morcom

    Sometimes gatekeepers are just people who maintain and operate gates to various properties. Sure there’s a couple bad apples, but the vast majority of them do good work. If I were a gatekeeper I would definitely get one of those portable TVs so that I could watch TV when work is slow.

    • Rich20Something

      Chris Morcom To be clear here, I’m not vilifying the actual gatekeepers as people. I’ve been a gatekeeper in the past. The big issue here is that sometimes WE (i.e. people looking to get ahead) mistake the gatekeepers for the decision makers. We assume that when they say no, it is the world saying no…and we give up before we can scratch the surface of our potential. So we have to get around the gatekeepers first.

      • Chris Morcom

        Rich20Something Chris Morcom Haha yeah I know I was just being a jackass. I agree and am glad you posted this. Also this whole blog/website has caught my eye. You write very well.
        But yeah…Life is too short to ask for permission. There are too many people in the world whose gut instinct is to say “No.” Nothing happens when you say “No” but anything can happen when you say “Yes.”

        • Rich20Something

          Chris Morcom Rich20Something For sure. And to tack another point onto that, a lot of times we disqualify ourselves first by saying “no that won’t work” before we even put our idea out into the world. In that case, we are out OWN gatekeeper. 
          That’s a fascinating mental barrier.

  • jnugent2

    It is always, always, always, easier to beg for forgiveness than to ask for permission. However, in the event that one needs to get through the “gate keeper” the successful tricks have always included “act as if”; Act as if you belong there, that you were scheduled to sing, that the “boss” is expecting you.  Presenting yourself confidently and competently may catch the gate keeper off guard; they will always fear upsetting their boss and take the extra moment to verify lest they get themselves in trouble for turning you away.  Depending on the scenario, this can provide you direct access to the decision maker or give you the chance to start “singing” while the gate keeper is away.

    • Rich20Something

      jnugent2 This is a great strategy, Jake. In many situations, it’s super-helpful to act “as if”. To respond to your email (better than writing this twice): you asked about specific strategies for getting around gatekeepers. I think it varies by what you’re trying to accomplish, or what field you are in. For instance, the singer in the example could have found a way around the barista. A med student can’t find his way around the gatekeeper that is med school. LOL. 

      Can you give me a specific example of a time when you wanted to get around a gatekeeper, but couldn’t find a way?

      • jnugent2

        Rich20Something jnugent2 First and foremost, your success will be directly correlated to the amount of effort you put in to your endeavor. This does not mean just your attempt at persuading said gatekeeper to let you [insert goal] but rather planning your attempt and having an idea of how to execute it. The gatekeepers and goals will always change however, getting through them requires the same planning.
        Ask yourself, ‘What method would work best?’ i.e. Bulldoze the gatekeeper (with confidence, false pretenses, whatever gets your foot in the door to make your pitch)  or appealing directly to them with your cause.  Secondly, ‘How to appeal to them?’; Employing the “WIIFM” (What’s In It For Me) review, identify what benefit they receive by letting you [Goal]? Does their quality of life improve by making an exception? Do they understand what they could lose out on by turning you away?  Again, the success herein lays with your planning (including a proper marketing concept which you should have already written and know cold).
        Remember, Without a Goal, You Cannot Score. Without a Plan, You Will Not Get a Chance to Take the Shot!
        In my line of work, there are always gatekeepers that protect the target client. These gatekeepers or advisors are relied upon to filter out the minutiae and only pass through quality opportunities. In finance (my area), these gatekeepers are generalists but not specialists on anyone given area. Further, they posses experience or skill(s) that have gained the trust of their client.  In proving a mastery of my niche, modeling myself to appeal to the advisor (they look good for passing me through) as well as modeling myself after other specialists (from other fields – what makes them standout in their field(s)) that were previously approved and passed through as well as educating the advisor just as if they were the client, on what unique opportunity I have or superior skill, I will have deployed my best efforts on getting through.

  • tomcool32

    Loved this post! Even though it’s a rant, it is something most of us thought of but never concluded the same way as you did! I am super happy I found this blog. Couldn’t have happened at a better time. I’ve just turned 21, out of college, learning web design on my own and you must have already guessed it, at HOME! Not that I am looking for a job, a couple of freelance projects help me convince my parents (gatekeepers?) that I can make something out of this. Super interested in UI and UX design. Working really hard to make it. Thank you Daniel DiPiazza

    • Rich20Something

      tomcool32 Really happy to have you as part of the community, Tom. Keep pushing. This might help you: http://www.rich20something.com/hacking-elance-the-step-by-step-breakdown-to-making-23700-in-4-weeks/

  • East Coast Girl

    In negotiations, the experts always tell you to find out who the gatekeepers are and go to them directly with your request. Ignoring the gatekeeper altogether and then asking for forgiveness is definitely another tactic we must keep in mind!

    • Rich20Something

      East Coast Girl They are both good solutions depending on the context and your goal. Can you give me a good example of when you ignored a gatekeeper?

      • East Coast Girl

        Rich20Something East Coast Girl I was just offered a promotion in my org but didn’t really want it – I didn’t see myself progressing down the same path as my boss. So I talked to someone else in the org who was higher up. He brilliantly suggested creating a new position for me that would fit my goals and interests better. I mentioned this to my boss and now we’re in negotiations about what this new position will look like! It hasn’t been finalized yet but I’m very happy I didn’t just go down the prescribed path and through the traditional gatekeeper – my boss.

  • Jackie104

    Yeah completely agree. Most people are in autopilot. Anything that takes them out or calls attention to them in a new and perhaps scary way,they will reject. Sometimes I like to mess with employees by asking them questions that actually require them to think. It’s surprising how many of them refuse to be human or think in order to help or solve a problem.
    Better just remember to sidestep. Good article, everyday life lessons.

    • Rich20Something

      Jackie104 Interesting to note, Jackie. And I agree. Funny enough though – we have to be careful when we say “most people”, because it usually includes ourselves as well 😉

      Can you think of a time when you were on autopilot?

      • Jackie104

        Good observation Daniel. I would say a good portion of my relaxed time, and certain daily repetitive taks. I make an effort daily to be conscious where I feel it’s important. It takes a fair amount of energy.
        I make an effort when interacting with others or pursuing my goals. And especially when helping others. I would say the trick is to set the best autopilot you can for a siuation but be alert enough to engage when you are being engaged.

  • Great article, Daniel.
    I came across your “How I Hacked
    Elance…” article a few weeks ago (put it to practice, and it worked!)
    and since then have started to dig into your other writing. This article
    is really cool and definitely demonstrates the whole ‘nothing ventured,
    nothing gained’ theory. Like you said: 99% of the time, people will
    just say no. It’s easy and requires no risk on their part. It’s
    important to remember that, most of the time, if you just do
    it…whatever it is…you’ll be glad you did and 10 steps ahead of the
    guy who didn’t do anything. Or who got held up by one of your ‘false

  • Rich20Something

    JoeTalls Glad it helped, man! Can you tell us a little bit more about your success with the Elance material?

  • owens346

    very good points in this one

  • adam5

    Your blog is so good!

  • ddsuber

    Definitely shouldn’t have asked permission.  It’s not a library where you have to keep quiet.  What’s the worse that could happen?  I’m not going to bad mouth employees who want to keep their jobs, but we can all afford to think outside the box once in a while.

  • ddsuber

    BTW, Daniel, also thanks to some of your sage advice, I am learning to code in 2014 through edx and codeacademy.  You’re the best!

  • Rich20Something

    ddsuber Hey Diana! That’s awesome! What made you want to start?

  • Rich20Something

    ddsuber Really cool!

  • ddsuber

    Rich20SomethingddsuberSomething I had read about lifelong learning and keeping the brain supple as we age.  I try not to make resolutions because I know I’ll be disappointed in myself if I don’t keep them.  So, instead I made myself a To-Do list of three things I wanted to do in 2014 and coding was one because people who have that skill set are valuable in the marketplace.  I then happened upon an article about codeacademy.com and then a blurb about this course at Harvard called CS50 being taught now on EdX.  The EdX course is broader–lecture plus projects– and takes you through several languages.  Code academy is more hands on and lets you complete tasks as you learn.  I find the balance of the two good so far.  Both are for people like me who have 0 experience.  And it’s FREE.

  • JulietAnnerino

    Great, powerful, fun and succinct post, Daniel! The same barista who is too afraid to say “yes” to a free concert will most likely also be too scared to stop a little free entertainment, if the crowd at the coffee shop likes it 😉