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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
gatekeepers.'
Thanks!
@JoeTalls Glad it helped, man! Can you tell us a little bit more about your success with the Elance material?
@Rich20Something@JoeTallsYeah, definitely. I signed up for Elance in March, but just kind of
hung out on the forums for a few months, occasionally applying for
jobs...with no success. I wasn't a very serious job bidder at first, I
maybe applied for one gig every week or so. But, if I ever got a
response back (which wasn't very often), it was usually asking me for
more samples...which I didn't have at the time.
Anyways, as time
went on, I did a few writing jobs locally...writing a print ad and a
press release (one for my employer, one for a friend who was opening a
restaurant), and eventually I got a writing job through Elance. I was
ecstatic, even if it was only a small, $50 assignment. I dug into that,
got it done, but it wasn't long before I was back to not having anymore
work. Now I currently have a full-time job, so money wasn't the
issue...but getting my writing business off the ground definitely was.
Randomly
Googling something Elance-related one night, I came across your "How I
Hacked Elance" article and read it front to back. Twice. It was some of
the most sound advice I had ever read and I constantly found myself
scratching my head saying, "Why didn't I think of that?" It wasn't long
after that I decided to put your advice to the test. So I found a job
posting...actually, one that I previously wouldn't have even applied for
thinking, 'I can't do this one. I'm not experienced enough.' But I
applied for it anyways doing what you said to do (i.e. researching the
client, finding out what they liked/disliked from former freelancers,
and incorporating those things into my proposal as my strengths.). But
the most important thing I did was follow your advice on turning my
proposal into a short video tailored to the specific job I applied for.
It
was harder than you made it look, that's for sure. But that might just
be a compliment to your skills. But anyway, after a few takes I had my
video proposal and I sent my proposal in. I'm not going to lie...within a
couple of hours I had a response back saying, "We notice you don't have
any feedback and not much portfolio experience, but your video really
made you stand out to us. I think we're going to give you a shot."
So
I got the job writing a full page magazine ad and I'm happy to say that
it led to a second job writing another full page ad for a different
company. And, if that goes well, who knows. I might just be their go-to
guy the next time they need a copywriter.
Sorry for the
long-winded response, but your article made a big impact on my business.
It led to my best portfolio piece to date, and soon-to-be my second
best piece. And, most importantly, it led me one step closer to dropping
the 9-5 and taking my life into my own hands and building the business I
never even dreamed I could even start.








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!
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!
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
KJ<>
Kevin Diamond hey Ken, thanks for being part of the community. You’re so right - it’s all about going to the source!
Hey Dan!… Yeh Gatekeepers!.. They’re around every corner and scared of success… They try to stop successful people from achieving their goals and are always ready to block the path…most of them have no idea why they do this…is a subconscious mechanism driven by their own fear… I always liked the analogy of Crabs in a net….. There is a phenomenon that fishermen noticed when fishing for crabs….they noticed as they raised the giant net to the surface, the hole at the top where the net didn’t quite cover the crabs, naturally allowed for a certain few at the top to escape….however, they were astonished to find that the crabs below would hold onto the legs of those that had the chance of freedom, trapping them and pulling them back. These are the gatekeepers in life…sometimes they can even be people in your own friends & family!… They don’t know why they do it…it’s just inbuilt into them…Yes! I agree!.. Finding a way to avoid the claws of the gatekeepers, is the first step towards the source of freedom!
Paul23 Crabs in a barrel, man. Now the real question - when these are people who are close to you…do you confront them, or just move on?
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.
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?
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.
@hazelmaepan Totally agree, and thanks Hazel - welcome to the community
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.
@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.
It was very inspiring Daniel! I think from the day we are born, most of us, are nurtured to become gatekeepers. The decision makers are the minority. And usually only these people nurture their children to be like them.
I also keep from your article that “Ask for forgiveness…but never ask for permission to demonstrate your worth or power.” This is what mostly keeps back the wannabe enterpreneur.
Hey Angelo - welcome to the community and thanks for the comment! You’re totally right - in many instances, it’s preferable to just DO the damn thing and not be so afraid.
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!
Liz Flores So true Liz! great story and reason why this is so injected in our nature!
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.
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.
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
Haha, stupid phone post. Let’s NOT be discouraged!!!
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!
Sam Barnes For real, man. Can you think of a recent example where you encountered a gatekeeper? What did you do about it?
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.
@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.
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!
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?
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.
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.
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.
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.
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.”
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.
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.
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?
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.
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
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/
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!
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?
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.
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.
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?
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
gatekeepers.’
Thanks!
JoeTalls Glad it helped, man! Can you tell us a little bit more about your success with the Elance material?
Rich20SomethingJoeTallsYeah, definitely. I signed up for Elance in March, but just kind of
hung out on the forums for a few months, occasionally applying for
jobs…with no success. I wasn’t a very serious job bidder at first, I
maybe applied for one gig every week or so. But, if I ever got a
response back (which wasn’t very often), it was usually asking me for
more samples…which I didn’t have at the time.
Anyways, as time
went on, I did a few writing jobs locally…writing a print ad and a
press release (one for my employer, one for a friend who was opening a
restaurant), and eventually I got a writing job through Elance. I was
ecstatic, even if it was only a small, $50 assignment. I dug into that,
got it done, but it wasn’t long before I was back to not having anymore
work. Now I currently have a full-time job, so money wasn’t the
issue…but getting my writing business off the ground definitely was.
Randomly
Googling something Elance-related one night, I came across your “How I
Hacked Elance” article and read it front to back. Twice. It was some of
the most sound advice I had ever read and I constantly found myself
scratching my head saying, “Why didn’t I think of that?” It wasn’t long
after that I decided to put your advice to the test. So I found a job
posting…actually, one that I previously wouldn’t have even applied for
thinking, ‘I can’t do this one. I’m not experienced enough.’ But I
applied for it anyways doing what you said to do (i.e. researching the
client, finding out what they liked/disliked from former freelancers,
and incorporating those things into my proposal as my strengths.). But
the most important thing I did was follow your advice on turning my
proposal into a short video tailored to the specific job I applied for.
It
was harder than you made it look, that’s for sure. But that might just
be a compliment to your skills. But anyway, after a few takes I had my
video proposal and I sent my proposal in. I’m not going to lie…within a
couple of hours I had a response back saying, “We notice you don’t have
any feedback and not much portfolio experience, but your video really
made you stand out to us. I think we’re going to give you a shot.”
So
I got the job writing a full page magazine ad and I’m happy to say that
it led to a second job writing another full page ad for a different
company. And, if that goes well, who knows. I might just be their go-to
guy the next time they need a copywriter.
Sorry for the
long-winded response, but your article made a big impact on my business.
It led to my best portfolio piece to date, and soon-to-be my second
best piece. And, most importantly, it led me one step closer to dropping
the 9-5 and taking my life into my own hands and building the business I
never even dreamed I could even start.