The Side Door Strategy: How to Achieve Goals

Everyone Told You Were Impossible

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Welcome to The Real Work, weekly insights for high-performers and entrepreneurs who've outgrown their current success and are ready to rebuild from their authentic foundation.

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I want to share a system that has unlocked speaking opportunities at SXSW, consulting contracts with Walmart and L'Oréal, and partnerships that completely changed the trajectory of my business.

It's not a hack. It's not about who you know. And it worked even when my life was falling apart.

In 2015, my life was in shambles.

I'd just been fired from Facebook. My father was in the hospital for cancer treatment. I was fresh out of rehab trying to put the pieces back together. And somehow, in the middle of all that chaos, I still had bills to pay, a family to support, and a business I was desperately trying to build.

I needed credibility. Fast.

Nobody knew who I was. Having Facebook on my resume only got me so far. What I needed was something that would make people take me seriously when I cold-emailed them or showed up at networking events.

That's when I decided I wanted to teach at NYU.

Not because I loved academia. Not because I had teaching experience. But because "NYU Instructor" on my business card would give me instant credibility with the entrepreneurs I wanted to work with.

The problem? I had no idea how to get hired by a university.

The FUBU Blueprint

I studied someone who knew how to get in front of audiences he didn't have access to: Daymond John.

When Daymond John was building FUBU in the 1990s, he had zero marketing budget. But he understood something more valuable than money: he understood his ecosystem.

His goal was to sell urban fashion. His ecosystem was the hip-hop club scene in New York City. If he could get people in those clubs wearing FUBU, word would spread everywhere.

But how do you get in front of everyone going to the hottest clubs in New York when you're a nobody from Queens?

Daymond mapped out who controlled access to his target audience. And he realized something brilliant: the bouncers.

Everyone saw them before walking in. They were essentially unpaid brand ambassadors that nobody was using. And bouncers had a problem Daymond could solve, they struggled to find fashionable clothing in their size.

So Daymond gave them free FUBU gear. No strings attached. No ask. Just value.

Suddenly, everyone walking into the hottest clubs in New York City was seeing FUBU on the guys at the door. Word spread. The brand exploded. All without spending a dollar on traditional advertising.

Identify the ecosystem around your goal, find the people who control access to that ecosystem, figure out what value they need, and give it to them before asking for anything in return.

That's exactly what I did with NYU.

How I Got In

My ecosystem was entrepreneurship education in New York City. The people who controlled access? Instructors already teaching the courses I wanted to teach.

And these instructors had a problem: they needed guest lecturers.

Most were adjunct professors juggling teaching with full-time jobs. They needed breaks. They needed fresh voices. They needed someone who could deliver value to their students and make them look good.

I could be that person.

So I started researching instructors at NYU who taught entrepreneurship and marketing. Found their LinkedIn profiles. Started engaging with their posts with thoughtful comments. Didn't ask for anything. Just showed up consistently and made my name familiar.

Then I reached out with a simple offer: "I noticed you teach entrepreneurship at NYU. I previously worked at Facebook and now run a consulting business. Would it be valuable for me to come in as a guest lecturer for one of your classes? No fee. Just want to give back."

First few people? Rejection. Or silence.

But I kept going. Eventually, one instructor said yes.

I showed up, delivered a 90-minute session on Facebook marketing, and crushed it. He asked me back. Then introduced me to another instructor. Who introduced me to another.

Within six months, "NYU Instructor" was on my business card. Doors that were closed before? Now open.

And I discovered something even better: I was really good at teaching. It wasn't just a credential play. It became a genuine part of my business.

At my peak, I was teaching multiple classes at NYU while delivering employee training for Walmart, Levi's, L'Oréal and Red Bull.

The side door didn't just get me in. It opened up an entirely new path.

Your Side Door Strategy

The front door is crowded, expensive, and controlled by people who don't know you. The side door is open, overlooked, and accessed by solving problems for people already inside.

The framework:

1. Define your impossible goal - What credential, opportunity, or access seems out of reach?

2. Map your ecosystem - Who already has what you want? Who surrounds them? Who do they depend on?

3. Find the gatekeepers - Who controls access but isn't the obvious person everyone else is pitching?

4. Identify their problem - What do these gatekeepers need that nobody's giving them?

5. Give first - Provide value before asking for anything. Make yourself familiar. Make them look good.

6. Let introductions multiply - One yes leads to another. Trust compounds.

This isn't networking. This is strategic problem-solving disguised as generosity.

It works because most people are too impatient to give before they get. Most people pitch before they build trust. Most people bang on the front door and wonder why it's locked.

Find Your Side Door (AI Prompt)

Copy this into ChatGPT or Claude:

"I have a goal that seems impossible or that I've been rejected from achieving. Help me develop a 'side door' strategy:

My impossible goal is: [describe what you want to achieve]

Please help me:

1. Map my ecosystem - Who already has what I want? What world do they operate in? Who surrounds them professionally?

2. Identify gatekeepers - Who controls access but isn't the obvious person everyone else is approaching?

3. Discover their problems - What challenges might these gatekeepers have that someone with my skills could solve?

4. Design my 'give first' strategy - What specific value could I offer before asking for anything?

5. Create my outreach plan - Draft a simple message I could use that focuses on giving value rather than asking for help.

Be specific and tactical. Show me the side door I'm not seeing."

Once you get your strategy, don't just read it. Execute it. Pick one gatekeeper from the list. Reach out this week. Give value before you ask for anything. The side door only works if you actually walk through it.

Get started

You're too talented to stay invisible.

The side door is always there. You just have to be willing to look for it, and walk through it.

Stay Savage,
Terry

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