Category: Setting Up A Business

Independence is…

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Have you ever been really frustrated at work and had a thought like, “I can’t wait to retire and be in charge of my schedule!”

Or better, “If I started my own company, I’d never need to lean on anyone – it would be me in charge!”

I remember in my employee days what kinds of things would trigger these thoughts. My boss telling me to do something I fundamentally disagreed with. Being asked to do things outside of normal work hours. Getting reprimanded for going outside the boundary to do the right thing.

The struggle was real!

So you can imagine that with the lustful lens of entrepreneurship, I thought that it was total freedom and independence. 

I didn’t owe anything to anyone. I was my own.

So maybe you think this too. 

Many people think these are pairs –



In reality, they are opposites!

Independence is enough self-trust to take on risk, challenge and fear to create our own opportunities, and to do so despite what others think is best for us.

Notice, this definition, one I had to sit on for a while, isn’t about freedom and attachment to others or demand, it’s all about our choices to operate of our self-interest.

So if we think about what we need to be independent, we also need sustainability. By Sustainability I mean that our own needs can be met because of our strength and skills and mindset – all four things stemming from financial, physical, mental and emotional health.

When I look at how the world portrays independence, it’s only considerate of us….

One. Not others. Ours only. 

It’s all about what we have, are, and can be. It’s all us and our ability to take and extract value. 

And the way most people would describe entrepreneurship is similar….

“It’s my ability to build a business that makes me money and takes care of my needs for success, significance, etc.”

Selfish language…notice it?

It’s an absolute opportunity to increase our earnings, happiness, work-life balance and several other things. But growth is the key. It’s an ability to satisfy our need to lead, or our need to be significant. It feeds our ego. It can feed our connection and growth too.

But to me, these are opposite. They exist in contradiction. 

Being an entrepreneur you actually INCREASE your dependency. Let me explain.

To be a great entrepreneur, you must be DEPENDANT, or better stated, INTERDEPENDENT

To solve problems, you need others, you need to listen, to hear, and to understand. For who will pay for your solutions? Where will this money you want to earn come from?

To solve problems you need to take action with, be a part of and immersed in a culture or community. How will your business be sustainable if you cannot stay a part of an economic ecosystem?

You need others – and without others, you cannot be an entrepreneur. From the macro, no one can be an entrepreneur alone. 

Expectations of being more independant is normal and simple to new entrepreneurs, but they in fact should relish the moments that create interdependance. These can exist in a lot of ways.

If you hire employees or teammates, or bring on partners, you are now INTERDEPENDANT – the success of one is the success of all. As is failure.

If you have a client that’s now a part of your business, you are dependent on them for revenue, and they on you for service. 

To misunderstand this is to devalue and shortside your growth as a business and leader. 

So, as you go about considering your next phase of independence, it seems logical to review what you believe independence to be and how it works.

Neighborhoods, communities, companies are all interdependent. Just like I rely on the mailman, UPS and FedEx to bring packages to me when I order them, trusting they will leave them in the mail area, I also trust that the residents where I live will not take what I’ve ordered for themselves.

Without this trust, there is no such things as freedom, but our freedom stems from Interdependence.

What’s something you depend on now that you are grateful for? Is it a person? A thing (car, train etc) or a place (gym, etc)?

Share your thoughts below!

The Mask: Change isn’t as Easy as It Sounds

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So maybe you’re starting a new job, or a new diet, or you got a new haircut.  You were supercharged about it, and knew it was the right call.

The next morning, WHAM – panic set in!

Why would you do this? What were you thinking? So stupid!!!! Damn it. Questions are firing quickly in your head like a fast-forward soundtrack of fear and loathing.

Suddenly, the emotional bravery becomes riddled with questions and fears and now that waters all murky and how will you ever undo this moment that’s permanent. SHIT!

It’s real – the things that happen after change are often harder than the change itself. It’s the self-talk and the way we internalize it all that bites us. The mask of fear is really scary.


So today, let’s talk about those feelings.

First things first. The feelings you’re experiencing are really normal.

You’ve gone through so much change at such a fast pace that it’s very natural for all of your systems to be at a breaking point try to keep you where you are.

But it’s significant and indicative of something really cool happening in your head! (you all know I’m glass half full, but this is true in more ways that optimism)

Your whole system is on the precipice of a major breakthrough and that’s why you’re feeling this. Your mind is saying “You know we’re not ready for this! Hold on now – wait a minute now! We need to do it my way!”

The feelings come from your system trying to keep you safe, and protecting you is the intention. But the system, the brain, is dead wrong.

Meanwhile, your subconscious is saying “We can let go of fear and make this change. We’re ready!”

This battle to allows all this change to unfold. The way you’re feeling, then, is really important part of the process. We’re talking about major recalibration and that that doesn’t happen easily, so this unrest that you’re experiencing is important to experience. It speaks to the growth you’re about to undergo.


What happens when we usually try to make change?

If you’re like me, a human being, you probably failed a few more times than you’d like to admit. I did.

I tried to start a new running routine. Failed. I tried to start a new gym routine. Failed.

What happens is you get all excited about the change, you go through it with excitement, but because you haven’t done the real work underneath the change itself,  but then your body freaks out and tries to pull you back to what you know, and you listen – you abandon the change and make some excuse up. For me, it was that I just didn’t like to run in the cold.

If we know this unrest and discomfort on the very edge of permanent change is normal, we can focus on accepting these feelings of anxiety and allow the change to take place.


All of this is very normal.



Asking questions and having doubts is also normal.

When you start to question yourself for the choices or this new path that you’re on, pause for a moment. Good work. It’s good work not just because of the above, but in general I believe we should be calling the stuff in question and verifying what we know as truth. Maybe it was truth and isn’t anymore. Maybe it still is. Maybe it never was. We must ask those questions!


I quit my job in May of 2015. It’s been 3 and a half years since I did that, and I can’t lie to you and tell you that I didn’t feel these feelings. It was scary. It was intimidating and I did have my fears and doubts win a few battles. I’ve been there. I would question the shit out of EVERYTHING, still do.

I still question my goals, and my path. I still have doubts. It’s not that those go away. Even as I climb up higher and higher into what I believe success really means, they are still there.

But I have trust underneath that all.

I even trust DOUBT.

I trust a doubt will creep in and I trust the doubt will continue to pull me away and I trust that doubt is part of the process. But that doesn’t mean that I trust the doubt itself, I just know that part of the process is doubt.

A question I get all the time: “I don’t know where I am right now – where am I?”

And sadly, that’s where most people stop! The fear takes over, and they don’t look for answers to the question. The fact that they don’t have an immediate comfortable answer (because they’re in the midst of changing the answer) makes it really uncomfortable. But there’s good news. That’s the best time to keep going!

It’s a great place to stop and pause and say “Hey, where am I?” with a more positive tone, and to get to a point where you can ask about what matters and what you want.

I know change is hard. But we must consider that commitment to change is the only way to make it happen in a way that serves us.

Sometimes what we want changes. And if we don’t know where we are, we can’t ask where we want to go. Both of those require some time investments, but the reason asking those questions is so important is that it creates good friction.



Our mind hates good friction, but our best self loves it and our body loves it.

Though, our mind, our mind likes to stay in safety.

Safety is another fun word for comfort and consistency and as you’re going through all these changes, you’re challenging comfort and consistency and your brain is wired to say no.

This is perfectly normal. Your brain is trying to latch on to what it knows, what would keep you safe.  And what will keep you safe is only based on what it knows. Without facing this emotion – you won’t change. Simple as that.

You’ll feel things pull you back as your brain cries out, “WAIT, no! Don’t go! Come back! It’s not safe there! STOP! NO NO NO!”

And here’s the start of the friction. Your reaction and response to this brain noise is the critical element to the change you want to make.

But this is just a mask.

Normally, the response is “I’m questioning it so therefore it must be wrong.” And that’s going to take you back towards brain safety. This is about getting out of safety because safety hasn’t taken you where you wanted to go in the first place. That’s why we’re making change, right?!?

I believe it’s healthy to question changes, reasons and motivations. I believe that when you’re facing the discomfort of making change, it’s important you endure it, and hear the thoughts you have.  Your whole world isn’t rattling, your whole foundation isn’t unstable. It feels that way, because there’s friction. We want friction.

Friction lets us know change is happening, so as uncomfortable as it is, invite it. Let the feeling happen. Go with some curiosity into it as you make your change and ask yourself why you feel this particular way.


“Is this what I actually want?”

“Is this the change that’s important to me?”

Those are key questions. If so, then you’re ready, and any friction you feel is just an indicator that you’re on the right path.

There’s a really important lesson here that comes with change.



First, you have something that you want. You get it, you get comfortable.

Then you set your mind to change. As you do this you build a new want and start to let go of the old want.

Seemingly obvious, we build habits around what we initially wanted, and now we are starting to let them go. This is where the friction comes from. Replacing an old want will drive you bonkers. Here’s an example:


I thought a career was the right choice for me. Then I met entrepreneurs and talked with my dad more. I eventually was letting go of the idea of a career and thinking I could be something else, something more. But guess what crept in?!?

Yup, doubt and fear.

My brain didn’t want to let go of safety, security, and all those things that come from following the traditional path. So, it was scary, and hard, and I had lots of friction. Friction internally, externally. Everywhere I looked I was getting mixed messages, especially the mirror. I remember sitting in my window and feeling so scared that I was wrapped in a blanket like a burrito, immovable.

I had to let go of one to get to the other side of change. You will to, but I believe in you.

Your brain is making a new connection. It’s unplugging one wire and plugging in another, and that’s going to cause lots of strange things to happen in your mind, especially in transition.


These new connections you’re making, these new synapse links and is actually you waking up to and experiencing the change you want to make. It’s happening – hence the reason friction is all a part of it.

The good news?

You’re now in probably the most beautiful of states.

Brain: I’m not letting this happen. [puts scary mask on]

Subconscious: I want this! Let’s go, get out of my way! Take that stupid mask off, it’s silly looking!

I want you to do the work and experience the discomfort anyway – because we are going to push through it and make his change happen. On the other side of this is everything that you want, is everything that you’ve asked for, is the alignment that we’re looking for – it’s right there!!


I know change can be scary, but change happens with this fear and chaos all mixed into it. On the other side is the beauty that you can be and can have.


If you’re dealing with change and would like some insight or someone to talk to, please reach out.



The Marathon and I…

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Marathon running is much like owning a business, quitting a job to start a company, or anything else that requires you to go the distance. This weekend I ran the Marine Corps Marathon, and wow did it go differently than expected.

Still, I learned a lot about the character and habits and mindset in place, and how this test is just a reflection of the others that are undoubtedly coming my way.

9 months of preparation. Nearly 500 miles of running logged, probably more if you count the non-tracked runs. There I was, in the presidential suite of the Double Tree near the Pentagon (and no, I didn’t pay for it, I’m a travel hacker – duh!).

I’m drinking water like it’s my job. I’m carb-loading like it’s the last bit of food I’ll ever get.

The Marine Corps Marathon was only 9 hours away.

I wake up early, 4am, get a little food, drink some more, and get into my meditation and visualization.

Wading through people and lines and drop offs, I get to the starting line and before I know it, I’m running. It’s chilly, but the run warms me up. I’m on pace for 3 hours in the first 6 miles, no big deal. I am smiling as I go by fan after fan after fan, watching families cheer on loved ones and fan-created signage that makes you laugh – i.e. Never Trust a Fart.

At mile 11, I’m moving at a good pace, averaging just about 7 minutes. I have lots of energy, but without any warning, my mind starts screaming at me to stop. Something’s wrong, but I won’t admit it to myself, and I refuse to listen to the weak thoughts.

WHAM. It was like someone hit me in the head with a sledgehammer.

Getting to mile 12, my head is spinning and I can’t run upright consistently. I tell myself I should stop for a break, then I battle that thought down. A few more yards and I can’t run in a straight line. I bump into someone as I try to find a way to the side, but I’m so unstable I can’t move my feet right. I waive for help, and two marines jog over just in time to catch me as I nearly start to fall over, no doubt assisted by a cramping right quad.

Sitting down, my world is on fire.

“You’ll never make it.”

“Quit now, and just go home.”

Among the list of marathon woes people experience, I don’t recall one saying “weak mindset.”

But here I was. Thinking about quitting.

After 20 minutes sitting, waiting for a medic, and then checking vitals still not feeling better, we called a medic over, but he took 10 to get there and another 5-10 to get to the aid station. By the time I got to aid, I was shaking. Cold, numb, and unsure of what I was going to do.

Some treatment, more vital checks. I’m laying under a space blanket made of ‘soft’ aluminum foil. And I can see out of the tent. I can see runners, who at this point are running a 5 hour time, a full 2 hours off my goal. But they are running!

Mentally I’m giving up. I’m angry and frustrated and sad – among other emotions – all at the same time.



Electrolytes, food, blanket. Stop shaking, and I’m sure I’ll be okay, right doc? He warns me that if I’m not showing signs of improvement, I should consider opting out.

Isn’t this message what we hear all the time? Play it safe…Make it easy on yourself, just don’t even try!

Just take it easy, go home and fall in line with everyone else. It’s easy.

This is the messaging we always get. Stay where you know it’s safe. 

(Let’s tie this back to business – THE WORLD DOESN’T PUSH YOU TO BE GREAT. ONLY YOU CAN DO THAT!!)

Thanks to whatever they gave me, a few minutes later it was like the lights turned back on. I could finally think clearly.

There was no fucking way I was not finishing this race. I had a PT massage my cramping right quad and hamstring, and hobbled my way out. Here we go.

The rest of the race was a series of fails and pains and cramping, but I got to the last hurrah and powered my way through it, despite cramping at nearly each step. Fuck it, why not finish, right?

If it isn’t overt at this point, I did not hit my 3 hour goal.

I wasn’t even close. In fact, I don’t even know my time. I don’t care.

Crossing the finish line and resting, I had two friends meet me. I started to eat some fruit, sad down, and on came the shivers. It wasn’t long before medics had to come back over and I was back in the damn tent again. Shaking, I get changed and sit with all kinds of stuff to help me get warm.



“Beginning stages of hypothermia,” the doc says to his team. We joke about it, and I’m laughing. I don’t feel good at all, but that’sthe irony – I somewhat love this space.

Yes, look how happy I look!!!!

By this space, here’s what I mean:

Odds against, and people telling me my best shot is to not continue (welcome to entrepreneurship my friends)

Overly fatigued, injured, but proud of what I’ve done

Mindful enough to know whatever pain I’m in or whatever I’ve suffered, better is coming and the current state is only temporary

Down, physically and emotionally, but never out

A few years ago, before I spent a 2 year period truly self developing with at least 10 hours a week, I would have had a totally different response. Here’s how, despite not making my goal and being SO far from it, this is still an event I’m proud of:

This will apply to any entrepreneurs reading and anyone that’s thinking of doing something tough – like quitting your job or having that conversation you’ve been avoiding.


Ask for help – there’s nothing wrong with it, and typically it’s just your ego that wants to fight for power dynamic wins. Take a deep breath, get clear on what you need help with, and ask for it. Find a coach, get a mentor, whoever you can! 

Be able to receive – people will help you but you have to be open to getting help. I had a long conversation with a friend of mine that really struggled with this. People would ask him, “How can I help??” and not only did he not have an answer, but he couldn’t accept the help even once he did! Be willing to accept what people offer, and you’ll have a much better go at your goals!

Finish at all costs – no matter what. Make it happen. Don’t worry about what happens, just make the decision to figure it out no matter what comes your way. It’s an outlook and perspective that becomes critical at higher levels too. 

Don’t do it alone, have people there to support you – seriously, back to point one and two. Get people around you that will help you get there. You’ve got this.

Whether it be starting a business, quitting your job, or running a marathon, I believe in you and your ability to make it happen. Focus in on the goal, and who you need to be to accomplish it. And after that, never look back!



What’s an area of your life where you could use these four to make RAPID change and finally get where you want to be?

Share below – and let’s figure out how to get you there!



How Great Ideas REALLY manifest…..

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I want to tell you a story about the things that businesses don’t tell you:

It’s not Genius that creates ideas.

So my blog, these articles, they are all about finding other ways to make money. Enjoyable ways. Liberating ways.

As an example, Really exciting news: This week, my business Ortus Academy, launches it’s third product.

We take kids through our game, NumisMatters, then through 10 lessons about money, including things like Earning, Saving, Value, Investments, Stocks, and Money Attitude.

It’s a ton of fun honestly, and it’s one way that I’ll make money this year. One of many, but they are all the same in the way they start……

I’m going to walk you through my process.




Behind the scenes of any big launch, or idea, or product are four key things, we’re going to talk about them.

First let me tell you how Money Club happened.

I got a call from a school, who liked what we had. I sat with the director, and we went over things that we already did, and what he wanted.

I said ten words, “Thanks for having me out. How can we help you?”

I didn’t say anything else for 20 minutes. I took notes. I thanked him. I left.

He essentially told me all of his needs, wants and fears, and then I had enough to go off.

Back at HQ, (fancy letters meaning our local coffee shop) we discussed whether it was feasible to make him happy. We called two other schools, got some feedback on the idea. Called teacher friends. Called parents, I still call my mom about these things, shut up.

And then we went balls-to-the-wall crazy into creating it.

So here’s my process.

This is how Convert Your Skills, a 1-on-1 course I offer that teaches individuals how to upstart income streams with a zero starting point, started.

This is how Ortus Academy started.

This is how I arrived at Pipeline Soccer Club to coach.

It’s all the same:

1. Be open
If you aren’t open to new things, how could you possibly build a business. A friend of mine is the most closed-minded person I know. He and I balance well, but he can’t run a business because everything is impossible. When you talk like that…it is impossible.

At one point, flight was impossible. So was going to Mars.

2. Listen
When someone talks, ACTUALLY listen. I know this is brave advice. It’s also the best way to get laid. Don’t blabber on, ask more questions and then shut up. Shocking how easily you can find hidden gems in business opportunities if you’re paying attention.

Heard everyone you know say that it’s time for someone to invent a better way to hold your keys, because they are annoyed by the jingling and searching…..well, maybe you have a business

3. Listen more
Think you’ve done enough listening… it more. Ask better questions. Ask more questions. Do research. Research and reading count as listening.

4. Try it like you mean it
We live in a world where it’s cool not to give a f*(*k. It’s embarrassing. So when you hear the things people want, and you do your research, and STILL it seems doable, that’s when you ditch all the inner “No, I can’t” and “I’m not sure” and get to work.

There’s a really awesome Branson Meme that’s fitting here. If you know him, great. If not, you should.







Maybe you have a different process? I’m curious what yours is! If not, steal mine!!!


Pay versus Purpose: 5 Lessons @ 5 Months

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It’s been some time since I wrote lengthy posts on this page….Hello, from the other side….(Sorry, that damn Adele song is on so much I had to do it!)



Things are different now, but for the right reasons. Today I’ll share a monumental change that’s happened, how it happened, and how it liberated me.

I sit at 2:42 in a Starbucks. My office is everywhere, and nowhere. I am currently handling ‘upkeep’ – email responses, small tedious tasks, and setting up meetings – for the upcoming weeks. I’m prepping for the launch of Ortus Academy’s Financial Literacy program. I’m researching community developers for a client, and designing a flyer for another. Compared to a year ago, I am less burdened (as in I feel less stress) while also managing to work nearly 2-4 times as productively.

On this side of the proverbial fence, there are three main things that a person can do in a day:

  1. Work towards a payment
  2. Work towards a mission or purpose
  3. Not work

At first glance it appears that number three is not a viable option in a lifestyle that is dependent on finding your own income sources, however, I’ve found that it’s actually an important aspect of this change. Because work and play are now so blurred, I have to work hard to define boundaries, create off-times, and disconnect, otherwise, I can’t recharge. More on that later.

Working towards a payment and working towards a purpose are clearly different in intent, and that brings me to my point today:

If you are focused on your payment, it becomes harder to be focused on your purpose.

Building a non-profit has been a tough challenge. It’s a lot to set up, expensive as well, and it takes time to do something great. Nonetheless, we’ve made progress. I, as the visionary, have gone through my ups and downs that most do – you lose sight of the bigger picture, and become intent on the short term snapshot as a reflection of your progress. When clear on where we wanted to go, in a big context, the smaller components have become easier to identify, goals have been easier to set, and progress is quicker to see.

Some days I eat my ego alive. Other days I thrive, confident to cockiness borders. Some days I’m virulent, other days I’m passive.

I’ve had the fortune to be able to make money in a lot of different ways.  Since leaving a full time job, I of course have to hustle to make ends meet. I trimmed my expenses by about 23%, knocking down smaller expenses and living within my means. I slimmed to only what I need to have and I cut out some fruitless spending in favor of a different method of getting my “shop” on. I took on some odd jobs, but by keeping my rates high, and using some arbitrage, was able to net well and maintain a low work rate. But making ends meet was never the goal. Naturally, I sacrificed the floor to take away the ceiling with the hope that I would earn more than I was before, but I also wanted to do things I loved – anything from writing, to reading, to getting healthier, to more youth involvement, more family time and deeper relationships. Money can’t do those for me, but smart work and smart time investments can.



Lesson 1: Barter, Barter, Barter



There’s real value in being able to trade. It’s an old school method, dating back to before money was even around. In the BC era, artisans and craftsmen bartered to survive, trading for what they could not create, build or grow themselves. Bartering has a poor stigma to it, as though it’s not approved, but elite freelancers and smart businessmen know a good deal doesn’t mean a pretty one.

I offer my services in exchange for someone else’s, and compare them and the value of them so that it’s mutually beneficial. Remember, there are limits that everyone has. Some people need cash in their business, so I’m not often put off if I receive a no. However, if it does work, I’m sure to have constant check ins to make sure both parties are happy.


  • No cash exchange means no taxes paid
  • Services that you normally wouldn’t have access to become available
  • Can still leverage the relationship for testimonials, references
  • You’ve still earned a client


  • While you’re not working for free, you’re still using your time
  • It’s easy to take advantage or be taken advantage of; consistent check ins are key
  • Your impulses may pull you to exchange for things you don’t really need


Lesson 2: Mentors and Persons of Interest – Give First, Ask Later




Since I no longer have a job structure to do it for me, I’ve become a professional networker. Sometimes I need some support in overcoming a wall, a good reference to an auto vinyl company, or a sounding board to make sure I’m on the right path. For example, you’d be surprised how quickly a reference can change your hunt for a qualified company, service, or person. I spend a lot of time building a network of trustworthy, reliable, high-integrity people. When I get stuck with decisions or choices, I lean on them for advice, but it didn’t start that way.

More importantly, these are the smartest, most prevalent names I can find, and their expertise far outweighs mine.  I like to be the weakest, dumbest, most inexperienced guy in the room.

To join their team, (and later, for them to join mine) I’ve employed a lot of different strategies, reaching people in and out of network for a multitude of reasons. Have a Person of Interest (POI) that would be a good mentor, a reliable source of advice, a great hub for meeting others, or is a personal hero? Here’s a few ways you can reach them with credibility and get them in your corner:

Before any contact, reflect on your POI’s WIIFM (What’s In It For Me). What can you offer to them? Second, can you clearly state what it is you’re looking for? Help, money, or a chat, isn’t specific enough for someone who gets consistent requests for donations of time or expertise.

Winning Strategies:

  • Solve a problem you know they face (you’d be surprised what you can come up with from online sources). Whenever you reach out to a new party, have an angle; give, offer, or supply something to them before you ask for something in return.
  • Connect them to someone that can solve their problem. You don’t have to be the guy they need, but if you can be the link between the two, you’ve become a strong utility, worthy of attention.
  • Find referrals from Friends, Family, or Close Colleagues of your POI
  • Approach the POI from two angles. If you know his confidant, and his personal trainer, and you can get a referral from both, you’re going to be more likely to make contact.
  • Have nothing to offer? That’s ok, but don’t hide that, in fact, share what you’re interested in and that you’re unsure of how you could make the relationship two-way.

Losing Strategies

  • Sending a long email shows that you aren’t respectful of their time. Keep it concise, and if it’s not concise, take the time to make it that way. Reminds me of the quote “I’m sorry this letter was so long. I didn’t have time to write a short one.”
  • Never, EVER, EVER lie about your connection to them, your interest, what you found in researching them, or how you can help them. It seems like a no-brainer, and I haven’t done it, but I’ve seen relationships crumble and reputations broken this way.
  • “People don’t buy what you sell, they buy why you sell it.” Process that before you move forward with an elaborate attempt to lure a high-quality person into your network.
  • Keep your communication relevant. If you’re off on a tangent, and you emailed me, I’d stop as soon as I lost you. Other successful people think that way as well. Time is limited.


Lesson 3: Be Bored, and Leverage Itimgres2


For the OCD, always going Dynamos like myself, the hardest thing to do is stop. Sometimes, I work so frivolity that I forget to eat, so I have to constantly work on this, personally.

This advice comes from my good friend, Jae Jin, a musician that was dear enough to impart some of his mantras with me. When you work for yourself, on yourself, or in your own business, you go, and when you aren’t going, you’re generally sleeping. It’s sink or swim.

Reflection, and problem solving, don’t come from mysterious places – the brain processes and breaks down solutions. They always tell you to take a 15 minute break at work, but how often does that happen? Now that I work whenever and wherever, I have to tell myself to walk away from problems.

But why boredom? That’s the polar opposite, isn’t it?

In order to fully launch into your pursuit, namely your purpose, your downtime is vital. Watch a TV show, get out in the sun, go for a walk, and sit in public with your phone off and in your pocket. When you start up again, go full throttle into what you’re doing and don’t stop til you’re dead tired, and repeat the process. The break in between has been the genesis of many a bright idea.

Suggestions for Boredom Breaks:

  • Turn your phone off and use your watch (whoa, I know) to track time. If you have an hour, give yourself an uninterrupted hour.
  • Watch a TV show, and let your mind wander into whatever it is that’s happening. Forget about the meetings, problems, employees, offers, and whatever else is up there. Let the clouds roll by for a while.
  • Do something creative (paint, draw, doodle, etc.) or exercise – both are known vices for entrepreneurs and freelancers
  • A sharp body is a fitting home for a sharp mind.
  • Read: Read for fun, read for research, read for reference. PRO TIP: Be careful on internet reading. It’s easy to get distracted and lost.


Lesson 4: Categorize Your Endeavors




It’s okay that you have to make ends meet, there’s truth in that. But, if you’ve ever been caught up taking on more than you’re used to, working longer than you thought you would, you can probably relate to feeling like you’re “in too deep” with a project you weren’t pumped about. If you’re onto your purpose, but a project is about your means, label it as such.

I’m not suggesting you prioritize one over the other, because your quality of work is important as a professional, but knowing you are doing something to keep yourself afloat, rather than to reach towards your purpose, is imperative. When things get stressful with your means, you can give yourself a reminder based on what’s most important, and what you’re main focus is. When I feel overwhelmed, I remember the impact I’m trying to make, rather than the money that I need to make it happen. That calms me.

Whatever method you use to keep yourself on track (calendar, white board, lists, chalk on a sidewalk, whatever), make another one, and separate it into two parts, labeled “Means,” and “Purpose.” The projects that you have get identified this way.


Lesson 5: Have Some Fun


I currently have 7 projects on my desk. Some overlap more than others, but they are all more deeply connected to WHO I am now than my projects were with a full time job. Someone assigned me that when I was their employee. Now, it’s my rules.

To be able to pick my projects is a blessing. I really do admonish and appreciate all that I have, and do so every day. Now, when I don’t think I’ll enjoy doing something, I can say no, or amicably walk away.

If you don’t love what you’re doing, you won’t put in 100%. I have so much going on, that when I put into a project, I HAVE to give 100%. Imagine training for an iron man (running, swimming, biking) and not training hard for any of them. When I’m on the grind, I’m going as fast and hard as I can.

Some tips to make sure you have fun:

  • I like to think of Aaron at age 30, 35 and 40; knowing I’ll get through it, what will he think about these projects looking back. Sometimes that helps me relax a bit and know that I’ll be ok.
  • I enjoy comedy. I put on comedies in the background when I’m creating art, creating material, or building programmatic materials. It makes me laugh and is good background noise.
  • Call a friend during a break. Ask them how they’re doing. When they ask you about you (since everyone answers in three words “things are good,”) really dive in and ask them for more info. See how they are REALLY doing.



For all those freelancers out there, I hope this is helpful. If you’re thinking about how much you dislike your job, because it misaligns to what you think your purpose is, then let this article be the kickstart to practice the above. Do it while you’re in your job, and you have little risk. After work, see if you can apply what I’ve learned. I bet it helps!



Creating a Pivot Point and Faith-Leaping

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Success Principles from my first go at a Non-Profit, Grantwriting, and Failing

In the last year, since telling myself that I was going to build my businesses and create opportunities to work for myself, I’ve grown a lot – personally, professionally, entrepreneurially, and even spiritually. I want you to be a part of the new journey – side-streaming into full entrepreneurship. But, behind that is a simple three steps to me being more bold.

How often do you take a leap of faith? I write that as though doing it were easy. I admit, I let fear dictate a lot of my decisions for a long time, and never took a GIANT leap of faith.

Then I had a revelation.

What if you could practice taking leaps of faith, so when you take bigger leaps, it wasn’t so scary? Well, if the Coach in me didn’t understand that practice makes perfect, who would?

So, for the last year, I’ve applied a three-step approach to the goals that I have, even small ones:

  1. Push past my initial self-created limit (The BREAK)
  2. Set up an if-then risk assessment (The FEAR)
  3. Place the decision outside of your direct control (The LEAP)

The concept behind this approach works like this:

First, by breaking through your initial limit, you’ll effectively start to see how most of the barriers that are in front of you are self-created. More often than not, we tell ourselves what we can and can’t do, and what we are and aren’t capable of. Creating habits of breaking past your own limit is a foundation for success, a topic we’ll talk more in length about.

Second, recognition of your worst and most vain fears is a crucial step to actual progress. Recognizing what we fear the most, and often times for me it’s been totally silly, is the first step towards making a dent in them.

Finally, it’s not often that we are comfortable letting someone else influence our lives, but that’s why we do small pivot points over and over – so that the repetition makes it easy and less scary.

See the common thread here: Repetition.

Think Kobe Bryant – he’s a master because he does the fundamentals 2000 times per day, not because he was born a master of the jumper.


  1. Push past your initial self-created limit.

Last week I went through Hell Week, hosted by Ramit Sethi and Mark Divine, a Navy Seal Commander. It was about setting tougher goals, crushing your own limits and recognizing the mindset that creates success. One of the things we had to do was blow through our physical barriers by recognizing that we had never set a high goal and had the methods to get to them. For example, one goal was to complete a 21-minute plank.

My reaction: “I like weird physical challenges, and I’m in good shape, but there’s no way I can do that.”

Response from Mark: “How do you know? Have you ever tried?”

I failed even at my own psychology on this one.

It’s such a simple principle, but pushing past the limit we made for ourselves is incredibly powerful. When you do it once you learn a little more about how to set goals and how to get to them.

In college we did some crazy planks for maybe 3 minutes, but all of those were nothing compared to this challenge. I ended up completing the 21-minute plank by focusing on 30 seconds at a time. Even if I had failed, fallen, and collapsed at 6, or 10, or 15 minutes, I still would have CRUSHED the limit that I thought I had – This is exactly what we want.

I thought of a million reasons why I couldn’t be successful at my own business and my passions. Eventually, I decided that was bullshit.

This year, I decided, with a partner, to take on financial literacy education. I’ve wanted to teach in a less fundamental way for a long time, so there were a lot of self-obstacles in my way. The goal was to create a non-profit, a 501 (c) 3 business, then get into schools where we could make impact. Instead of a head on approach, we established a partnership to build with a school, that way we had a better idea of their needs, and could tailor to them. This would better ensure a ‘product’ that would sell, not to say that would make it easy.

We set a really, really tough goal. I didn’t even know with certainty we could do it….that I could do it. We wanted to have a product (educational programming) for launch in the spring. We wanted to develop a Pilot program, and $5000 would be enough for us to do a tremendous amount of hours with the kids, so we applied for a grant. While we worked on writing the grant proposal, we worked 20-40 hours a week on developing the product, the brand, and everything we could. We didn’t think we’d have enough to write about, or wouldn’t have the data or the costs, but like Parkinson’s Law tell us, we completed the task in the time we set forth for it. We submitted the grant, hopeful we could teach financial literacy to Baltimore youth, 2 hours before the cutoff. I never thought we would. We broke our limit.

The BREAK taught me a lot. I’d never written grant, never started a non-profit, and never built an educational product. But, like the first time I had sex, I was nervous and anxious and, of course, eager. In the case of sex, even at 18 (late bloomer, here) I knew the outcome was worth facing the fear, but for something like this, there’s not a pretty woman on the other side telling me how awesome it would be. Now I know, it’s totally worth breaking through the limit, and feels just as good.


  1. Set up and if-then risk assessment

Applying for the grant and planning to launch a Pilot in the spring wasn’t easy. It took some balls to request money for something we didn’t have yet. Working from 5pm-11pm a few nights a week, we probably went through 564 K-cups, 29 gallons of creamer, and 16 lbs of organic grass fed butter. The Keurig recently bit the dust, too. L

When we sat and submitted the application, we had a drawing board out (my windows), and started a two column chart to track what would happen if we got a yes versus a no. We were playing chess with failure and success, so that we were two steps ahead – even a failure didn’t render us forfeited.

If we got the grant, we’d need to have the product ready. We’d still have to go to the school and get approval to launch. We’d need minimal supplies, but with some capital, we’d make it work. Our biggest crunch – if we got the grant, we’d need to find staff. That was our challenge. We sat and analyzed how we could find staff, bring them in, and what it would cost to do so. Planning for success was soccer 101 and we were at halftime – tied 0-0.

We planned for failure, too. If we didn’t get the grant, we had to either use our own money to fund the project, ask the schools to pay for it (which we didn’t want to do), or find another grant. We would have to reposition, reach out to other companies and see if they were willing to fund the pilot. We set down a firm but delicate objective if the grant didn’t come through. We would not give up, we would continue to work on honing our product, and we would try to get in front of more people to showcase our after-school program.

When we really analyzed the worst case scenario, we wouldn’t have lost much, but working so hard in case we heard a yes was going to give us a lot of progress.

The conversation where we really analyzed our FEAR, the absolute worst case scenario, was priceless. We didn’t have to close shop, didn’t have the earth collapse, and didn’t lose any credibility. When we figured that out, we knew it was the right decision to press forward and stop worrying.


  1. Put the decision outside of your direct control

Submitting the grant was a small “out of our control” decision in the big picture, right? But we still had to overcome something big within ourselves. We couldn’t really go any farther without funding, and though we continued to hone the product and the audience, we still needed to get money. Which comes first, money or the product???

We leapt hard.

No product ready, just hope, a goal, and some grit.

When we sat down the next day, you should have seen the realization that we had on our faces. Shit. We have to have a product ready in 30 days. Good thing there are services like Amazon Prime for coffee.

By taking that small leap of faith with the grant, and knowing we had a month to go before our intentional launch, we started taking more action. That meant shaking more hands, talking with more schools, and asking for help and support. We had experienced the first taste of faith-leaping. The benefit – propulsion from the expectation we put forth of ourselves. It was a cool drug. Motivated to deliver a happy handshake to that check writer was going to be a good feeling.

We poured in hours to the product, the curriculum, and the system. It was moving so quick. We we’re going to finish this in time. On the day before we got the word, we stayed up late, printed our flyers and materials, and had everything ready for the school. It was exciting to see and feel the work we’d done in our hands.

The email came the next morning and we got on the phone before we opened it.

We didn’t get the grant.

A wave hit us. Failure. Loss. Depression.

Then another wave hit us. We had already taken 3 other leaps into other funding options, school relationships, and partnering opportunities. Momentum was compounding. We prepared for this, just stick to the plan.

The LEAP taught me that when I put a decision in someone else’s hands, it motivated me to be a better representative of their decision. If I got picked to run a program, I wanted to make them look good. If I get picked to speak at a conference, I want to kill it, and if I client picks me for his project or as a consultant, I want to bring massive value.

But, until I placed that decision elsewhere I was stuck – with all that control comes little motivation to break out of the comfort zone.

Training the faith-leaping skill is like anything, you have to do it before you can say you’ve done it, and one comes before two. Before I knew it, I was approaching these leaps more and more – creating sustainable relationships, taking on mentors, longer lasting business deals, and more solidified goals.

When I really looked at it closer, what did I have to lose anyway?

Since you might be wondering, we still haven’t found the grant that will pay for everything, but we did manage to squeak a small grant out of someone that we did contact through our outreach in our middle step. It netted well ultimately, because it’s a partnership that could grow.

Now, as I go to embark on even bigger leaps of faith, I remember that if I push myself to the limit, and I’m prepared and ready with some risk-assessment (at least as best as possible), then the rest will come. That’s not to say I won’t fail, but business and personal growth doesn’t come from not failing, it’s from finding a way to keep moving and keep going after the failure.

There’s beauty in taking leaps of faith, and I intend to take them from here on out. At the end of the day – what the heck is there? No risk, no reward, and certainly no fun.

First, we BREAK our limit.

Then, we face our FEAR.

Last, we LEAP.

The Big 3 Takeaways from My First $20

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I can hardly recall what I had for lunch earlier today, but I will never forget the first time I earned $20.

Free work yielded a referral, and I got a call a few days later. He told me about what he wanted, his vision, and how long he had before he needed a design. Everything was smooth. Until….

“What do you charge?”

“Um. Well. Uh……”

A few more seconds of frazzle.

“I guess $20 an hour. It’s probably a four hour job,” I said shakenly.

Truth be told, I had no idea how long it would take. I did, looking back, a moderately good job. This small sale put me on a whole new journey, one that I’m still on today.

So let’s dive into some lessons learned while reflecting on the origin of it all.

I made a ton of mistakes selling my artwork and graphics, learning to coach (which is selling my product to parents and delivering to youth – a complex business scheme) and building a revenue tracking system for a large corporation.

I learned faster when I messed up, versus when I was successful. Mistakes force you to adapt NOW.

My first $20 taught me three things, the hard way:


  1. If I’m going to make money doing something, I have to take myself seriously and project that.
  2. Before I sell anything, I should know what it costs to do so, whether that be time or supplies.
  3. If I’m not ready to name a price and offer my services, I don’t have to. I can make the proposal in the way that I’m comfortable, where I can articulate my ideas well, but I have to approach it the right way.

That’s not to say that success isn’t awesome, either. I know that I would have killed for some input on a second income when I got started, just to know someone else was feeling the same way. With success comes a lot of things, and I remember these three awesome thoughts that I hope you have too:

“I can make money doing something I love”

“I got paid to do this, and I don’t have any education in it.”

“I am not even that good yet. Imagine if I could get 10x better what I could make.”


Let’s get straight to it:



  1. Be More than a Hobbyist

 If you’ve come here to side-stream, or to improve it, you need to make sure you are always using this word in conversation when you bring up your talent, work, passion, or job.


Professional: (n) – engaged in a specified activity as one’s main paid occupation rather than as a pastime.

I met two clients after starting just from putting my profession out there when they ask what I do. I am quick to distinguish what I’m doing for money (ex. presentations) from what I do for fun (ex. snowboarding).


Here’s an example:

Brian: “I’m a dog walker for big breeds in the Norfolk area.”

Frank: “I’m a professional dog walker for big breeds in the Norfolk area.”

At this point, Brian is saying “I’m a hobbyist.” There’s nothing wrong with that, unless he’s trying to earn money from this approach. I know absolutely nothing about dog walking, but I know Frank is making money doing it and that he’s got an area and a type that he serves.

Whether you are making $3 or $3MM, you are a professional– you do your work for an exchange of cash.

You want the fact that you do your craft, love or solution for money conveyed and yes, you say it even if you haven’t sold anything, yet. It is an important distinction.

As Side-Streamers, we should be projecting that we do this for money and we have a specialty. Put it out there.  People want your help, your expertise and your ideas.

Don’t just say that you’re a photographer. Tell them you’re a professional photographer and you do family shots at carnivals. I’m not a presentation guy; I’m a professional presentation designer that loves to spice up talks for persons of interest. Don’t make it up, but share it!

It’s awkward at first – work through it and continue to use it. The more you say it the better it will feel and the more it will resonate.

How many times have you heard someone say: “Maybe we should hire a professional,” or something to that effect. You want to be in that group, so assign yourself that title.

Bottom Line: Use the word professional and mention your specialty.


  1. Know Your Costs

When I got asked my hourly rate, I was on the spot and nervous. I didn’t know, so I sold my time for $20/hr. That one worked out. But only because my service didn’t involve costs at that point.

Fast forward a year, to where I was doing some digital paintings on the side. I posted a shot on Facebook, and got a request from a friend for a copy. I was so excited. $30 I screamed!

Turns out printing was $20, and shipping was $8.

Print, Pick Up, Pack, Ship, Cash Check = $2 Profit. Wow.


I don’t like focusing on what I’ll get out of a client initially, after all, that’s what makes me a good Side-Streamer. I want to be obsessed with knocking my service out of the park!

Still, you need to know, roughly, what things will cost when you take on a project. Remember, information is EVERYWHERE. What supplies do you need? What software are you using? What about travel time? Sometimes it’s not that easy, but I urge you to take time to write it all out. (If you’re on the spot, see takeaway number 3!)

Am I telling you to have a figure down to the cents of it – no. But if someone says, I’d like you to build a presentation for my 5-minute talk, I know it will take me a few hours of image editing for that length of time in a presentation, and even more the arrange the images in a logical display. I can’t quote him a $100 pricetag. I won’t do well on an 8-hour project.

Bottom Line: Get familiar with your costs to produce. Maybe it’s zero, $40 per transaction, $15 in shipping per sale, or a flat space rental of $50/hr. You can’t earn until you know what the cost is!



  1. Carrot & Stick Technique: Displace Estimate & Beat Competition

If you don’t know the guy that rambles and quizzes you about a project and 30 seconds later says, “What will it cost?” then count yourself lucky.

Many numbers people will try to intimidate you to do complex math like you’re Stephen Hawking.

See, I won’t forget this guy. I had quoted him $20/hr for four hours. It took 10. I wanted the job, but I lost my balance back from that overly type-A question right in my face. I wasn’t prepared.

The Carrot-and-Stick Technique relies on you having good communication, and it’s a two-part process.


The CARROT… (at the meeting/phone call/etc.)

I think better about my work not standing in front of someone, so I make sure I’m give myself the chance to do that. If I’m asked for an immediate quote, I say something like:



“Before I give you a price I’d like to ask you some questions,

get a feel for what you’re asking for exactly, and then map out my idea and what

it could cost. You’ll have a full idea of what I would do and an accurate estimate of the cost.

I’ll get your email and I will send you a full description and proposed price later today/tomorrow/reasonable deadline.

How’s that sound?

Notice, I made this entire thing about him. I didn’t say – “I need to calculate my potential earning at home.” It’s about me giving him a fair rate and great service. [Bonus Point if you work professional into this kind of statement]

As a Side-Streamer it’s important we make EVERYTHING about our client. (Join the email list and learn ALL about this in the Guide to Price Your Side-Stream)

Simple fact of business – if someone is paying me, it doesn’t matter if I love it, it matters that they do. You have the tools to nail it right here:  Read the Boomerang Technique to prevent missing what they want from your service

A few here and there will demand a price on the spot. I manage to give them a fair range, but ask for a moment to think, go to the bathroom, or pop out a cell phone and do some math. “I can give you a best guess range, and then follow up with more details later.” I tend to overinflate these numbers if they are pushy, just because they are being difficult.


The STICK…(the communication before the pitch)

There’s no easier way to beat competition than by great communication. Send an email when you get home to thank them for meeting with you, like this:


“Hey ____________.

 Thanks for meeting with me yesterday. I’ll be working on your estimate today

and will get it to you as promised by [deadline you gave].  If you have any questions

in the meantime, feel free to ask them!”

It’s an easy a business gesture shows you listened. You want a happy customer experience from the meeting to the quote to the estimate.

As you lay groundwork for a good relationship of service to your client, build your pitch around what you already know about him or her.

Next, you’ll send him your estimate, and don’t think you have to have a perfect excel file emailed to him – do what makes you comfortable. If you’re better with numbers, use numbers. If words suit you, do it! When you email someone your price, you’re sending them a pitch or proposal. If all you do is write a dollar amount, you’re missing a HUGE opportunity.

Don’t be afraid to really put time into your pitch. They will notice. For high conversions on a proposal, read my guide here.

Bottom Line: If you’re pressured, put the game back on your terms by effectively communicating with your client.




In essence, I learned that:

– There are people that want me to do free work, but I dispel them quickly; I’m a professional.

– Making money requires spending money. If you know what you would spend, you’re set to earn.

– Communication and a two-step approach are identified with high-value service.



What did you learn from your first Side-Stream money?

Approach: Angry Clients and Tough Conversations

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I remember watching a segment on the news by a professional pick pocket. Three news anchors were standing in an open room, several feet away, nervous and protective of their belongings. The pickpocket was not going to get anywhere near them.

He knew that he could never get to their things while in front or behind them. It was confrontational. He had to approach differently. By keeping the team from feeling confronted, he got shoulder to shoulder with his prey. He had managed to defeat the peripheral defense, and now was standing right where he wanted to be – in your personal space.

But why does he need to distract you? Read more