Ask For What You Want

Ask For What You Want

Ask for what you want. Most of the time, the answer will be no. Ask anyways. People who seem out-of-reach are only an email, text, phone-call, or social media direct message away.

You talk yourself out of asking because it’s less difficult than asking. When you ask, knowing the answer will probably be no, then you are willingly doing something with a high likelihood of failure. That’s not fun. But is it worth it?

Possible outcomes if you ask:

  1. They say no. You end up exactly where you started.
  2. They say nothing. You end up exactly where you started.
  3. They say yes! You get what you want.

Nobody will get angry at you for asking for what you want. At the very least, asking the question is an expression of self-confidence which will feel good. If the likelihood that you will get what you want is extremely low, asking might even feel exhilarating.

Possible outcomes if you don’t ask:

  1. You end up exactly where you started.

Send the email. Make the pitch. Ask. Take it from Steve Jobs.

Photo by Sharon McCutcheon on Unsplash


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How I Got a Paid Apprenticeship With One of the Best Videographers in my City

How I Got a Paid Apprenticeship With One of the Best Videographers in my City

4 months before getting hired, I had never been paid to make a video.

Video cameras were always intriguing to me. But beyond making skateboarding videos as a kid, I didn’t have any real video production experience until I decided to pursue it full-time in the middle of 2017.

At the outset, all I had was a little Canon T6i (great starter camera) and a vague idea of how the industry worked.

Newton’s first law of motion states that an object at rest remains at rest, or if in motion, remains in motion at a constant velocity unless acted on by a net external force.

This is why starting from scratch is so difficult. When you are at zero, there is no external force pushing you towards progress. That force is driven solely by your self-initiated effort over time.

Every creative field contains a Feedback Loop. The bigger and better your portfolio, the more clients you will attract. And the more clients you attract, the more opportunities you’ll have to add to your portfolio. Before either of these pieces is big enough to feed the other, you must add to them separately and, unfortunately, for free.

At this point, I had no customers, no leads, and nothing in my portfolio. My only option was to take that very first, daunting, lonely step forward and put out a video.

I Started Cranking Out Videos

I started vlogging because it seemed like a fun way to document my story, add to my online portfolio, and practice making videos. My first piece was mediocre at best. My second piece was slightly better, and the improvement continued with each new video.

Having a mediocre portfolio is better than having nothing at all.

As long as you keep adding to it, it will slowly become less and less mediocre. It didn’t matter that I had no paying clients yet. I kept putting out videos. This is a long-term game and there are no quick fixes.

Because I was staying busy working on my craft and developing my style, when I met somebody new I could confidently tell them that “I make videos.” This sounds better and inspires more self-confidence than saying “I’m planning to start a video company.”

For several months I put out at least 4 videos per week. I built up a solid backlog of content on YouTube and Facebook that I could point to as proof that I was creating things.

(Photo by Jakob Owens on Unsplash)

Vlogging consistently helped me chisel my own style. Since it was fun and I was ultimately doing it for myself and not for clients, the process helped me develop a video format that worked for my personality. My own creative freedom was in the driver’s seat. I used a certain type of music, certain types of transitions, and told my story in my own way so that it was discernible and unique.

I Contacted a Mentor

The core of success in any creative field maps from the two pieces of our aforementioned Feedback Loop: paying clients and a killer portfolio.

I’m a learn-by-doing type of person. I learn best by watching someone do what I want to do and then jumping in to try it myself. Naturally, one of my first steps was to reach out to somebody in my field who had a good handle on these two pieces and a well-oiled Feedback Loop.

I used these two things as a compass to locate a mentor.

Signs of a killer portfolio:

  • At least a couple thousand Instagram and Facebook followers
  • Upwards of 100+ videos on a Vimeo or YouTube page
  • A well-produced demo reel
  • A great looking website with sample content on it

Signs of paying customers:

  • Plenty of good reviews on the business Facebook page
  • Customer logos and testimonials on the website
  • Branded videos on a Vimeo portfolio

I searched around for “video production companies in Charleston, SC” and found Vive Media. They checked all the boxes. Looking at their online profiles, it seemed like they were doing what I wanted to be doing and were a couple years ahead of me. Perfect!

The abstract goals I had in my head began to find their form in a real, practical model.

When I first reached out to Matt, the founder, I was not set on being hired — I simply wanted to build a mutually beneficial relationship and put myself around somebody who was a couple years ahead of me. I knew I would soak up habits, mindsets, and tactics that would speed up my development, and I knew that in time I would identify a spot to provide value for him.

I found him on Facebook and sent him this: “Hey Matt, I’ve been checking out Vive Media online. I just left my job and am beginning a deep dive into photo/video. It looks like you’ve built up a pretty cool company and I’d love to hear your story. Can I buy you a coffee this week or next?

I was honest with him about what I wanted and I had a clear ask that wasn’t too forward. I didn’t go straight to asking to work with him or to teach me anything. It’s a long-term game.

We had coffee, I told him what I was up to, asked about his company beginnings, and we decided to keep in touch. I kept focusing on creating my own content.

While his professional portfolio was miles ahead of mine, he didn’t have any YouTube videos that were more personal like I did. The next time we met up, he asked me about my YouTube strategy and how I approach documenting my story.

I didn’t need to sell him on my understanding of this topic because I had already demonstrated my value by consistently creating videos using my own unique style. My portfolio, while new and not generating income yet, spoke for itself. Visiting my YouTube channel told him everything he needed to know. It showed that I was someone who knew how to consistently document a personal story using videos.

I let myself create what made sense to me, and the result was a unique body of work that resonated with a small group of people.

I positioned myself to offer value — then did it again and again and again.

I was by no means the vlogging “industry guru,” but I was 90% ahead of the average person by simply doing it (as opposed to talking about it or planning to do it). I had successfully positioned myself to provide value for someone who was several years ahead of me in my industry.

The second time Matt and I met up, he told me enjoyed watching my videos, noticed my unique style, and had a desire to create that for himself. I gave him all the tips I had from my experience documenting my story on YouTube. He mentioned that he wanted to document some of his projects behind-the-scenes to show people his process and connect with them on a more intimate level. I encouraged him to go for it.

During every meeting I made it very clear that, while I wasn’t actively searching for an apprenticeship, I was determined to learn as much as I could and that I admired his work. I offered to assist him for free on any projects he might need a hand with.

Several days later, he asked me if I wanted to help him shoot a YouTube video. I happily agreed, and we had a blast shooting the video.

(Photo by Sam McGhee on Unsplash)

Weeks later he asked me for help on a video interview project. Again, I happily agreed because the more I can work around someone who has more experience than I do, the better. This time he paid me for my time.

By working together, we each discovered more about our own strengths and weaknesses and how they complement each other. For example, Matt has a better eye for production quality but I’m strong when it comes to interacting with people and asking good questions in a video interview. These two strengths work very well together.

I continued offering to do anything he needed help with. It turns out he had a big project coming up that required a lot of emailing and scheduling. He also wanted some more behind-the-scenes content (similar to my vlogs) done for some of his bigger projects, and needed assistance with shooting and editing.

We eventually turned our working relationship into an official paid part-time apprenticeship.


You can’t just go up to someone who is more successful than you and ask them to be your mentor. This is a cost to them and, frankly, a waste of their time.

If you want an apprenticeship or a mentor, you must carve out your own way to be valuable to them. Luckily, you have an advantage that you might not be aware of: a low opportunity cost. Zak Slayback has a great article on this concept as it is applied to the professional world.

Having a low opportunity cost means that you can justify spending your time doing lower-value tasks more than a person with a higher opportunity cost can.

Because Matt had several years of running a video production company under his belt, his portfolio, relationships, and tacit knowledge in the industry earned him a higher opportunity cost than mine. That means I had a unique opportunity to do lower value tasks for him like scheduling and assisting on shoots.

My low opportunity cost paired with my consistency publishing content turned my creative hobby into a paid apprenticeship within 4 months.

If you take any piece of advice away from this story, it should be to create your own content. Remember, this is a long-term game. Don’t rush to be paid if you’re not quite there yet. If you focus on consistently doing your thing, opportunities will reveal themselves to you. You will carve out your own style and people who value what you create will notice. The Feedback Loop will start rolling. Just keep creating.

(Featured photo by Jakob Owens on Unsplash)


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Fleeting Mastery

Fleeting Mastery

“An infinite game [is played] for the purpose of continuing the play.”

–James Carse, Finite and Infinite Games

The more you learn, the more you find out how much there is to learn. When you decide to go into a particular field and as you continue down the rabbit hole, mastery in that field seems fleeting. Every new concept you learn is accompanied by 10 more concepts you didn’t know existed, let alone understand.

When I bought my first DSLR camera a year ago, I didn’t know much about photography, videography, or cameras in general. I started with the basics. I consumed as much as I could to understand ISO, shutter speed, focal length, aperture, and every other basic photography concept I encountered. Even that was overwhelming. It took many hours and reps experimenting with settings on my camera to develop a practical understanding of how the camera settings affect the final product.

After the basic settings, you can dive into different types of photography. You can dive into videography or different types of cameras. You can dive into editing, and within that transitions or keyframes or any other pieces of the puzzle.

I was overwhelmed, especially when I looked at other people who had much more experience than I did. Mastery seemed out of my grasp. But once I accepted that there will always be more unknown than known, I started enjoying the process. I didn’t see each new puzzle piece as a tiny part of a big puzzle that would take years to solve (I’m very impatient), I saw it as the only thing that existed in my world at that moment. The problem I was facing was sitting in front of me just like the next one would be after I solved this one.

Mastery is not a point reached, it is a mode of operation. The fact that there are infinite number of things to learn means you have infinite time to practice operating like a master. It’s not about learning certain things. It is about embracing and mastering the process of learning things.

When you stick in one field for 10+ years, you will learn a lot, you will understand how little you know, and you will develop a true love for the process of learning.


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Be a Practitioner

Documenting, blogging, podcasting, making videos, and talking about what you do is a very good thing. You should show your progress and share it with the internet. It will bring you resources, connections, experience, and much more.

But that should be a minor detail of your life. You’ll come up with more things to say when you do more things. Spend most of your time shutting up and doing things so you have something of substance to say when you open your mouth.


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Work Will Solve All of Your Problems

Work Will Solve All of Your Problems

I paced back and forth on the sidewalk, looking at my feet. I glanced up–this was a cookie-cutter neighborhood in the heart of the suburbs. Every house looked similar, and they were lined up along the street no more than ten feet from each other.

It was a nice day. It was cold, but the sun was out. That was rare for February in Ohio. I could see my breath.

My heart was pounding so hard I could feel it inside my ears. It reminded me of the feeling I got before hopping in a freezing cold shower. In what seemed like half a moment I made a split decision and started up the driveway. Before I knew it, I was on the porch knocking on the door.

Clipboard in hand, I hoped with every ounce of my body that nobody would open the door. I was muttering the script I came up with the night before. I heard footsteps. A man opened the door, and my mind went blank.

I can’t tell you exactly what I said, because frankly I don’t remember. It’s all kind of a blur. What I can tell you is that after whatever had left my mouth reached his ears, he looked at me as if I was crazy.

“Not interested,” he said, and I felt helpless as he slowly closed the door on me.

After the door clicked shut, something unexpected happened. The most overwhelming sense of relief came over me. I did it. I had just made my first cold call. 1 minute ago, I wanted to curl up into a ball and roll home–now, I felt exhilarated. Adrenaline was pumping through my veins. I wanted to do it again.

I marched over to the next house, pounded on the door, and gave it another shot. The rest is history.

That was the story of my first-ever cold call. It was the first of my marketing efforts for my painting business when I was 19. One month after that day, I closed my first $2,500 deal. Five months later, I wrapped up my first $60,000 summer.

I learned a lot of lessons that year, but one in particular stands above them all. This lesson stands so firm that I decided to write a book about it. I have doubted it many times, only to be repeatedly reminded of its importance. Are you ready? Here it is:


Yes, work. Work has been the answer to every problem in my life. It has been lead domino that has led to every success I’ve experienced. It is the common thread between those who succeed in the real world and those who fail.

There’s a lot more to it than you think. I’m not talking about putting in more hours in order to get more done. I’m not saying you should prioritize your work over other important things in life like relationships and play. I’m not telling you that getting a second job will solve your problems magically. It’s much deeper than that.

Call it self-initiated motion, call it taking action, call it being proactive, call it stepping in the driver’s seat of your life–I call it work.

It is the thing that all successful people have in common. They put themselves into motion decisively. They aren’t always sure where it will lead, but they think, decide, and act quickly. They don’t mull over what else they could be doing, and they don’t let wait around and wonder what will happen or what could happen. They accept the uncertainty of their circumstances, and they get to work.

I’ve talked to a lot of successful dropouts. None of them are prepared. None of them feel as if they have all the knowledge and experience necessary to do the things they want to do. Instead of trying to get to that point, they just get started, trusting they will learn as they go.

They all have a sense of self-confidence balanced out by a sense of rationality. They know they’re under-prepared. They don’t pretend like they know what they’re doing when they’re starting something new. They trust their ability, not to know exactly what to do beforehand, but to figure it out in the moment. They aren’t afraid of putting themselves on the spot.

This doesn’t strictly apply to careers. It applies to relationships, free-time, hobbies, and everything else in your life. If you want something, put the work into make it happen. Nobody else will do it for you.

P.S. I’m writing a book this summer. Click here to join the pre-launch list.

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Why Buying an RV was the Best Career Decision I’ve Ever Made

Why Buying an RV was the Best Career Decision I’ve Ever Made

A little over a year and a half ago, I had a tough career decision to make. There were several options in front of me which didn’t make it any easier. I had just quit my job and published my first book. I could have gotten a job at a startup, or I could have stayed at my old company making a comfortable salary.

I had a vision for education that I wanted to share with the world. I couldn’t contain it. So I did what any clear-thinking individual would do: I sold most of my belongings and took out a loan to buy an RV.

I believed (still do) that most people are wasting their potential in school. I believed that they’d be much more equipped to take on the real world and build a life of their dreams if they went off on their own and didn’t rely on their teachers. This belief felt so right, but it was so unpopular among the people around me. I felt like my ideas didn’t make sense to anyone but me, but something inside me knew that wasn’t the case.

I had something to prove, so I set out to create a movement. I wanted to do this in the most “me” way possible to show people that following their gut instead of their teachers is what will lead to success and happiness.

I’d always loved adventure and exploration, so I decided to embark on a on a cross-country RV tour to spread my vision for education by talking to college students about it. I didn’t have the money for this and I didn’t really know what would happen. I didn’t have much of a concrete plan either — I knew I couldn’t possibly plan that type of experience out from the start. But I knew exactly what I wanted, so I resolved to figure it out as I went. I just jumped in.

You can read the full story here.

Long story short, I failed. I ended up broke and unemployed living in an RV within 6 months. I was forced to paint houses for a month over the summer just so I could afford to eat. It sounds like a pathetic ending to a story, but to me it doesn’t feel that way. I have an enormous amount of pride about this entire experience.

I’m proud because I had a belief and I bought into it completely. I bet on myself. I burned the bridge behind me and allowed myself no way out but forward. I had conviction.

I set out to do exactly what I wanted regardless of the way people viewed it. I was willing to buy into my vision. Failure was a possibility all along, and I was OK with that. I knew I was doing this for the right reasons. Plenty of people called me stupid and weird, but that didn’t matter. At the end of the day, I did all of it for me. The fact that people thought me weird didn’t change the way I went about it, and it certainly didn’t change my goals or my desires.

On top of all the self-knowledge I gained on this journey, and despite my failure, this choice brought me to a group of people who shared my vision for education. This group is called Praxis. Now, I work for Praxis where I get to help people start their careers by relying on their ability, not their credentials. It’s a dream job that I didn’t think would exist.

I believe this happened because of my conviction to do the thing that felt right regardless of all the negative noise around me. Most people drift through life trying to please everyone but themselves. Their actions depend on how they will be seen, and they avoid the potential embarrassment of failure at all costs.

The best opportunities come when you bet on yourself.

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