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Success Advice

How to Get Through the Gatekeeper and Connect With Anyone

5 Insider Tips from the assistant to Robert Greene, a 6x NYT bestselling author 

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What is a gatekeeper in business?

Think of the bouncer at the door of an upscale restaurant, the muscle sorting out who to let in and who to keep out. Likewise, successful business professionals, politicians, authors and VIPs have someone that is in charge of protecting their time and space, letting in only a few based on certain criteria. You may not be aware of the power they wield, but it would be wise for entrepreneurs seeking contact to take heed of what it takes to get through the gatekeepers. 

Do your research first

Stop, look and listen. Your business could transform when you connect to the right people, so take the time to research your target connection before sending that email. What are their goals, struggles, and to whom have they already granted time? 

Prior to reaching out, spend time on their social media reading current and past content. Review everything on their website and listen to their interviews. 

5 insider tips from a high-profile assistant

1. What not to do

Do not approach with entitlement! While Stanley Goldberg, Robert Greene’s assistant (6x NYT bestselling author with his most recent being The Daily Laws), tries to give people the benefit of the doubt, some requests come in aggressively and cross the line. For example, complaining about the speed of an email response. No one wants to put a person like that through! Persistence is appreciated, but there is a difference between persistence and being demanding, and it’s usually those without big platforms that can be belligerent. If you approach with respect, an assistant will usually respond graciously as they know they are acting by proxy; it’s their boss’s reputation on the line. 

2. Recognize the privilege

An assistant is very careful with their boss’s time. As insiders, they witness the day-to-day diligence of how their boss takes their craft and business seriously. Scheduling, coordinating podcast interviews and appearances, managing social media platforms, and working on getting their boss’s name and business out to as many people as possible is usually part of their job. 

Goldberg is strongly aligned with Greene’s mission of teaching power, mastery, and psychological topics on human nature to the masses and believes that all people can benefit from at least one of Greene’s books. Working with the hope of somehow touching someone’s emotions so that they are prompted to buy one of the books is a very gratifying and privileged part of the job.

If you are a huge fan, say so! Detail what you got out of a VIP’s work, and be respectful in your communication, as that goes a long way in obtaining a possible connection. When asking for time, ask for a short time frame. It could be extended if you get a meeting and it goes well.

3. Provide value 

Who are you? Make sure that you include valuable accomplishments of your own in your email by way of links, a bio, and anything you have had success with, such as a podcast. Gatekeepers often go through it all, as they are looking to include whoever they can on their boss’s schedule. Additionally, many successful people like to pay it forward and help out a smaller podcaster and entrepreneur. While they can’t grant everyone an interview or personal interaction, they hope that people are respectful of that. 

4. Add a personal touch

Be vulnerable! Show that you genuinely care about the person and their work. Your courage in taking a shot at connection is admired by the assistant that knows what it takes to reach out to someone who is more famous and accomplished, trying to get a piece of their time that will mostly benefit you to grow your audience or impact your business.

Additionally, your personal request may not initially seem like the usual interview or connection granted, however if it seems like an unusual and interesting conversation may develop, you could be put on the schedule.

5. Be patient

Many gatekeepers have a lot of respect for the person they are working for as they are up close and personal with them. They are calculated with their boss’s time, making their own work-related interactions concise. When an assistant replies to an email asking you to contact them again in a few months, most do not – so keep trying.

Be confident and go for it. Goldberg says he himself got the job by a stroke of luck. While he had a love of publishing and marketing he was working as a soccer coach in NYC for kids trying to figure out his own direction when he answered a Tweet put out by Daily Stoic, and landed the job coveted by many.

In conclusion

Some additional tips: Use social engagement as well as your own network to get a referral and make a connection that way. Maybe someone you know could connect you. As far as who will benefit from the connection, think about how it will benefit them as well. 

Can you solve a problem for them? Value the gatekeeper, their perspective, and their job. They could end up putting you and your company in a strategic place on the map you could have never otherwise reached.

Esther Fink is an award-winning copywriter with awards from Oprah Magazine, Proctor & Gamble and others. She has a Masters in Organizational Psychology and combines psychology and writing to go viral.

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Life

9 Harsh Truths Every Young Man Must Face to Succeed in the Modern World

Before chasing success, every young man needs to face these 9 brutal realities shaping masculinity in the modern world.

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harsh truths for young men
Image Credit: Midjourney

Many young men today quietly battle depression, loneliness, and a sense of confusion about who they’re meant to be.

Some blame the lack of deep friendships or romantic relationships. Others feel lost in a digital world that often labels traditional masculinity as “toxic.”

But the truth is this: becoming a man in the modern age takes more than just surviving. It takes resilience, direction, and a willingness to grow even when no one’s watching.

Success doesn’t arrive by accident or luck. It’s built on discipline, sacrifice, and consistency.

Here are 9 harsh truths every young man should know if he wants to thrive, not just survive, in the digital age.

1. Never Use Your Illness as an Excuse

As Dr. Jordan B. Peterson often says, successful people don’t complain; they act.

Your illness, hardship, or struggle shouldn’t define your limits; it should define your motivation. Rest when you must, but always get back up and keep building your dreams. Motivation doesn’t appear magically. It comes after you take action.

Here are five key lessons I’ve learned from Dr. Peterson:

  • Learn to write clearly; clarity of thought makes you dangerous.

  • Read quality literature in your free time.

  • Nurture a strong relationship with your family.

  • Share your ideas publicly; your voice matters.

  • Become a “monster”, powerful, but disciplined enough to control it.

The best leaders and thinkers are grounded. They welcome criticism, adapt quickly, and keep moving forward no matter what.

2. You Can’t Please Everyone And That’s Okay

You don’t need a crowd of people to feel fulfilled. You need a few friends who genuinely accept you for who you are.

If your circle doesn’t bring out your best, it’s okay to walk away. Solitude can be a powerful teacher. It gives you space to understand what you truly want from life. Remember, successful men aren’t people-pleasers; they’re purpose-driven.

3. You Can Control the Process, Not the Outcome

Especially in creative work, writing, business, or content creation, you control effort, not results.

You might publish two articles a day, but you can’t dictate which one will go viral. Focus on mastery, not metrics. Many great writers toiled for years in obscurity before anyone noticed them. Rejection, criticism, and indifference are all part of the path.

The best creators focus on storytelling, not applause.

4. Rejection Is Never Personal

Rejection doesn’t mean you’re unworthy. It simply means your offer, idea, or timing didn’t align.

Every successful person has faced rejection repeatedly. What separates them is persistence and perspective. They see rejection as feedback, not failure. The faster you learn that truth, the faster you’ll grow.

5. Women Value Comfort and Security

Understanding women requires maturity and empathy.

Through books, lectures, and personal growth, I’ve learned that most women desire a man who is grounded, intelligent, confident, emotionally stable, and consistent. Some want humor, others intellect, but nearly all want to feel safe and supported.

Instead of chasing attention, work on self-improvement. Build competence and confidence, and the rest will follow naturally.

6. There’s No Such Thing as Failure, Only Lessons

A powerful lesson from Neuro-Linguistic Programming: failure only exists when you stop trying.

Every mistake brings data. Every setback builds wisdom. The most successful men aren’t fearless. They’ve simply learned to act despite fear.

Be proud of your scars. They’re proof you were brave enough to try.

7. Public Speaking Is an Art Form

Public speaking is one of the most valuable and underrated skills a man can master.

It’s not about perfection; it’s about connection. The best speakers tell stories, inspire confidence, and make people feel seen. They research deeply, speak honestly, and practice relentlessly.

If you can speak well, you can lead, sell, teach, and inspire. Start small, practice at work, in class, or even in front of a mirror, and watch your confidence skyrocket.

8. Teaching Is Leadership in Disguise

Great teachers are not just knowledgeable. They’re brave, compassionate, and disciplined.

Teaching forces you to articulate what you know, and in doing so, you master it at a deeper level. Whether you’re mentoring a peer, leading a team, or sharing insights online, teaching refines your purpose.

Lifelong learners become lifelong leaders.

9. Study Human Nature to Achieve Your Dreams

One of the toughest lessons to accept: most people are self-interested.

That’s not cynicism, it’s human nature. Understanding this helps you navigate relationships, business, and communication more effectively.

Everyone has a darker side, but successful people learn to channel theirs productively into discipline, creativity, and drive.

Psychology isn’t just theory; it’s a toolkit. Learn how people think, act, and decide, and you’ll know how to lead them, influence them, and even understand yourself better.

Final Thoughts

The digital age offers endless opportunities, but only to those who are willing to take responsibility, confront discomfort, and keep improving.

Becoming a man today means embracing the hard truths most avoid.

Because at the end of the day, success isn’t about luck. It’s about who you become when life tests you the most.

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Change Your Mindset

Work-Life Balance Isn’t a Myth: Here’s How to Actually Make It Happen

Work stress doesn’t have to win, here’s how to protect your peace and thrive in any workplace.

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Image Credit: Midjourney

Starting a new job often comes with excitement and ambition. Yet, beneath that initial enthusiasm, many employees quickly encounter the reality of workplace challenges, especially stress. (more…)

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The Four Types of Happiness: Which One Are You Living In?

Most people chase success only to find emptiness, this model reveals why true happiness lies somewhere else.

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In a world driven by rapid technological growth and constant competition, many people unknowingly trade joy for achievement. (more…)

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Success Advice

11 Mark Manson Lessons That’ll Redefine Success in the Digital Age

Success in the digital age isn’t about hacks, it’s about the raw, real lessons Mark Manson actually lives by.

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Mark Manson life lessons on success
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In 2016, Mark Manson released The Subtle Art of Not Giving a F*ck, a brutally honest, thought-provoking book that redefined self-help for a new generation. (more…)

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