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When it comes to landing your dream job, I have some advice and POVs that go slightly against what most people talk about.

But I really believe in it. If you read and execute on these five steps, you’ll put yourself at an advantage to level up your career and land your dream job over time.

1. Give value for free

This is something that some people push against, especially in the freelance world. But when it comes to landing your dream job, I think it’s a very effective strategy.

The best way to start when you’re building a side hustle, business or career is by giving value for free.

Even to this day, I get an enormous amount of compensation for my time and effort, and I’ll still do things for free for people. I’m still going on podcasts that have a handful of followers. I’m still taking meetings and giving free advice to people who don’t pay me anything.


I’m building value and leverage. I’m also building my reputation – so you’re more likely to say good things about me behind my back.

Same thing applies when you’re trying to build your career or your side hustle.

When you do free work for people, you build relationships that could lead to other opportunities. You never want to give with expectation, but it’s okay to ask. And those asks could lead to bigger and bigger opportunities that let you eventually charge a lot for your work.

It’s not an easy process. But nothing great should be easy.

2. When you do free work, do it strategically

It’s one thing to do free work for anyone.

It’s another thing to do strategic free work that brings you opportunities.

If someone asked me to speak in front of a million people for free, I’d say “yes” because it’s an opportunity to build my brand in front of so many people. A big reason I take so many meetings with rappers and hip hop artists and bring them value now is that I want those relationships.

I want that exposure.

Getting exposure can give you leverage

So many people push back hard against getting exposure. People say that you need to “pay the people” and “pay for the quality of the work.” I agree.

But the truth is, money is not the only way to pay people for their efforts. Short term money is not always the most valuable thing for someone, depending on where they are in their career and what they are looking for.

Simply giving someone an at-bat to prove themselves or exposure for their work on a grand scale can be a great way to compensate them. That exposure can be leveraged to land their dream job later.  

For example, there are a lot of people on Team GaryVee who work for me as creatives or videographers who get hit up for other opportunities after they start working with me. If they want to go work for another celebrity, influencer or even start their own business, the brand association of working with me could be incredibly valuable to them.

Be smart about choosing who you work for

Like I said, you never want to give with expectation. But at the same time, it’s okay to ask.

In this live stream call, Aubrey Marcus and I took a call from a guy who wants to build a side hustle sharpening knives for restaurants. I told him to start by sharpening knives for free for five of the biggest restaurants within a 30-mile radius to gain some experience and results.

And if the vibes are feeling good, he could ask a restaurant owner to shout him out on Instagram, give him a testimonial or send other referrals.

My only reservation with choosing who you work for and hitting people up is that many of you are going to turn into spam bots.

That is, you’re literally going to press “copy”, go into your DMs, and just start spamming random people.

So I’m going to quickly talk about how you can bring them value:  

For many people trying to sell their services or work for someone, their entire strategy is predicated on, “what can I get out of this?”

Of course you could DM The Rock, Tyra Banks, or some startup founder you love, but if you don’t consider what that person actually wants, you’ll never get through.

Here’s a better way to do it:

Step 1: Open up Instagram Direct Messages.

Step 2: Find someone you’d be interested in doing free work for.

The key is to find someone who has a solid following or presence that can give you the exposure you’re looking for. For example, if you’re sharpening knives, it would be smart to hit up some of the biggest restaurants in your area. It would be smart to hit up some of the kindest restaurant owners you know who might reciprocate and give something back.

But at the same time, it won’t always be practical to target the biggest.

If you’re a fashion designer, you might not be able to get the attention of Gucci or Armani, but you could hit up early to mid-tier companies and influencers to get your foot in the door.

Step 3: Direct message them.

Send them a message like:

Hey Gary – I love your work. I do social media and marketing. I would love to make 5 – 10 videos for you for free? Look at my account and lmk. Much love

— [your name]

The message would be tweaked based on what you’re trying to accomplish, but you get the idea.

Step 4: Do it consistently

You’re not going to get a “yes” on every DM. But the best part is, you really only need one “yes” to build your foundation.

Do this 100 to 500 times a day.

Step 5: Deliver

Once you get an opportunity, you have to deliver.

These DMs and offers for free work are just to get your foot in the door. At the end of the day, skill and execution are everything.

3. Make the most of every opportunity you get  

When you get an opportunity, it’s super important to really, really crush it.

If you’re working for free, the benefits you’re getting are mainly coming from the results of your work.

Take the time to perfect your craft so you can deliver.

4. Don’t underestimate the value of long-term connections

People always get caught up in this idea, “what if I do free work, and I get nothing back?”

I get it.

Let’s go back to the “knife sharpener” example. If you’re hitting up restaurants and sharpening knives for free, there might be a time when you don’t get anything in return. You might work for someone who’s just happy to get the work done for free and move on.

But here’s the thing:

Someone is always watching.

Even if the restaurant owner doesn’t give you exposure or referrals that lead to your dream job, the chef might have seen how hard you worked. And when he or she opens up the number one restaurant in town in three years, they’ll remember you.

Think in terms of years and decades, not months or weeks 😉

rejection from your dream job

5. Map your actions to your actual ambitions

I’m stunned by how many people want to be the best in the world at something, yet don’t put in the work to make it happen. It’s important to map your actions to what you actually want to accomplish – whether that’s your dream job or something else.

If you don’t want to be all-time at your field, you might not have to work as hard. You might be okay with maxing out at $67,000 / year while taking vacations and playing softball every night. I think that’s amazing, by the way.

But it’s important to be self-aware about what your actual goals are and map your behavior toward that.

If you got value from this article, it would mean a lot to me if you could share it on Twitter!

Check out the full live stream with Aubrey Marcus for more of my thoughts on this topic: