Quitting the Job: Takeaways and Outside Resources

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So, I’ve decided in two months, I’m going to leave my job. I am taking away a lot from it.


It’s time for me to take my side-stream main stream. This has come from a lot of work, strategy, planning, faith and support, but I wanted to share a little more of the gritty side of things.

The path to this decision has illuminated a lot, some about others, more about myself and what I’m capable of, what I’m fearful of, and what I could stand to improve.

Here’s some things that I’ve noticed by building my own business, working hard in someone else’s and being successful enough to choose in ways that you can apply to your own life, Side-Stream, or business:

Mental Shifts

Preparing to leave my job has illuminated some of the biggest changes in my operational objectives, my approaches, and my attitude. As I did more and more side work, the usual approach at work became an obstacle, rather than a learning process for success.

At my company, we value things like “it’s just the way we do things here” and “just follow instructions.” At first, it seemed like a recipe for success – just do it this way and you’ll never fail.

I guess you can say I understand it better, and now, I see that as a failure to comply with change, and as things have changed around us, we’re behind the 8-ball trying to play catch up.

Company Routine and Culture

In Corporate America, some major philosophies ring true to the company culture. When you have no idea what else is out there, it’s very easy to seem normal. I have to complete tasks that have no bearing on anything. They don’t increase sales. The reports indicate nothing relevant and go no where special. Responses dragged a conversation on and on for politeness rather than getting down to direct solutions.

I ended up stuck, just working for work’s sake and getting comfortable with it.

Remember in Captain America, when all the soldiers were challenged to get the flag for the sergeant? They are trying to climb the flagpole, and Rogers lets them fight, scramble and fall before pulling the pin and lowering the pole to the floor. That’s how I want to approach work.

It’s not a bad thing in a big company that relies on checks and balances; but it’s a terrible thing for an in-the-making-entrepreneur.

With 3 businesses open,  I had to learn to use my time better, be effective AND efficient, and make things happen over going through the motions. I became methodical. I researched, I calculated.



When I have a problem, I aim to solve it in one go – and that’s been new for me. Long gone are the days of emailing back and forth to maintain political correctness. I realized I was spending my time reading, writing, and ‘rithmaticking my way away from getting results.

You know that friend of yours that’s like “I want to find a girlfriend, but it just never works out…” and keeps trying the same thing. Nothing in the approach changes, and when he gets the same results, it’s a mystery somehow?

Yeah, well that friend is also most of us in the corporate world. At work, it’s ok that I spend my time doing things the same way over and over, even if it’s slow and ineffective. Have a better idea? Oh, just get it approved. Approved, my least favorite word – an erosion of empowerment.

In my own businesses, that doesn’t fly. I don’t have time for that. I have to get results fast. I’ve failed time and time again, but I keep stretching for the big wins, and let the small wins and losses go. If my work can be completed in 4 hours, why am I sitting at my desk for 8? If I can take data, rearrange it so I can audit it faster, why should I worry about the format? I don’t want to work all day for no yield, but I’ll work all day for the right yield. Only way to do that – let results be your measurement, not time investment.



Risk averse or not, we all take risks. We get our heart-broken, we leap, we fall, we shoot, we lose. It’s a part of life. In a system that’s already set up for you, one that lacks empowerment, we’re conditioned to be mundane. Follow the rules, they say. Follow the guide, they say.

Well, nothing is constant, and if you’re not growing, you’re declining. So many of my friends say, Aaron, you’re quitting?? Why? Look at what you get, look at what you have, look at where you’ll go if you stay! That’s an oxymoron friends. You can’t stay AND go.I chose to go.

Weigh your options, look at the good and the bad, evaluate the worst case scenario and dive into your worst fears. The more you think and talk about it, the more you might realize what you’re most afraid of isn’t really that bad. Wanna know one place we never EVER weigh risks until impact is unstoppable? Health factors like obesity!

I am most afraid of having to move to my parents house. After it’s all said and done, that’s not really the worst thing that could happen to me. Embarrassing, painful, and degrading, but I’d do it if I had to, and I’ll work 3x as hard to prevent that.



A floor to launch from has been the birthplace of what I’m doing now, and I can’t say that my new opportunity hasn’t been afforded by my current job, what it allows me, and the people that pushed me. Security is alluring when we’ve been told there aren’t enough jobs to go around. We want to feel safe, comfortable. Lose the ceiling, lose the floor – it’s only with the risk of both that I can find the stars.

Don’t get me wrong. I’m not cashing out my 401k, trading in my salary, and giving up health insurance for a gamble. I’ve calculated, built upside revenue, saved up a healthy years’ worth of expenses, and prepared like this was the olympics – but it’s still a risk. Calculated risk is different than gambling, and I’ll support the former, not the latter.

Play blackjack, and never take any more cards than you’re dealt- you might win a hand, but you’ll bleed your money away very quickly. My thought on risk – by risking nothing, you risk everything.



Most of my friends on social media will see this post title, or my pictures, and assume that this has all happened overnight, that it was a reaction, and that it was a lucky draw. The fact is, I sat down and wrote down my goals over 2 years ago. I penned them, my friends signed the page too as witnesses.

To say that it has come quickly is true – but that’s only looking backwards. In reality, it’s been a really hard climb to get to this point, and I’ve had to endure a lot to prepare for this. Like any athlete, competition is more than physical endurance, it’s setting up a system for mental preparation, development, and sustainability. Endurance and stamina are part of success – if you quit, you’ll never get there.

Leaders (aka small business owners and entrepreneurs) need patience. The toughest part of being patient is staying focused on the goal, and recognizing that the medium, path or methods may change along the way, but as long as you’ve set a goal and continue to work it, you’ll get there.


Learning and Failure

I don’t use a recipe when I cook. 92 times out of 100, what I cook is going to be awesome. Well blended, tasteful, bold, and even healthy. 8 times, it’s going to be awful – just not a good balance of tastes and ingredients.

Water always flows the path of least resistance. So do humans. At age 14, the girls that I coach are terrified to be creative, to think outside the box. It’s a real challenge for me to develop curriculums (yes, I develop those for sports) that force them out of their comfort zone. They won’t do it on their own, neither will you, neither will I – so I had to create system to force myself out it often and without thinking.

I’ve learned so much this year, mostly from my failure. There’s a lot of learning that goes into an experience outside of our comfort zone. There are six things we learn as a child that help determine our view of the world, and the risky play they engage in build valuable neurological connections. During your childhood, did you get introduced to these? Do you still fear them now?


Brilliance and Specialization are Bullshit

Do you guys remember that kid in middle school that got super good grades, the perfect SAT score, then went on to college on a full ride? I’ll never forget him. Those people may find success, but they certainly haven’t been equipped to fail the same way, and even more, they aren’t built for the kind of ride that most of us go through.

Talent is important, but I don’t think that’s a component of success. In fact, studies show being called “talented” is dangerous – it implies you won’t have to work, and you will just find success.

There’s money in being able to sit down and find correlations, common denominators, and linkable lessons. My approach is very “Jack of All Trades.”

You don’t need to be the best, just better than the client or better than average. Either gets me paid. Ironically, being a “generalist” means I’m more uncommon than an expert – every field has an expert. How many people can connect multiple roles, schools of thought, and backgrounds and blend them to a single thread? Not many.

Steve Jobs, though some may argue he was an expert, he was a generalist that could predict, captivate, engineer and engage on many platforms simultaneously.

By being able to communicate effectively, which takes understanding, promotes opportunities.


Hard Work

I know my work ethic has created this opportunity. It’s not without sacrifice that this opportunity yields itself to me. I gave up friendships, chances at relationships, family time, vacations, summers, fun, weekends and even money to make this dream happen. I can recall strings of 16-18 hour days, 7 days a week, to get things moving. I have no days off. I work around the clock sometimes. I am exhausted a lot. I have big dreams, but without the hard work you put in, that sweat equity is zero and your investment is rendered illiquid.

It seems too easy, from the outside. You don’t see the small things, and I don’t need people to: the results will do just that. There’s bragging about what your work ethic brings, but there’s also sharing. I like to think I’m doing the latter, illustrating the success that can come from hard work. Richard St. John paints the picture of other successful people and what pieces they had to their journey.


Money and Materialism

Money matters. But, interestingly enough it’s not what motivates people, says science.

So why would I walk away from money, from an awesome apartment, and from a stable, secure and easy salary?

Usher, 2004, Simple Things – They say money can’t buy you love; It’s the simple things in life we forget.

I won’t let my job be my prison. As soon as I realized I was working for things and shit I don’t need, I realized I work really hard for a whole lot of obligation – and worst of all, the working harder didn’t net me any benefits over working at an average level.

If I make enough to cover my costs, my life needs, and I’m happy – the money will come with the big wins I pursue. I like the control factor in that, but I also like the uncertainty in it all. There’s a better way to work, and I promise it doesn’t involve desking it all day and running reports through the roof, just so I can buy something I don’t need.



I live in an apartment out of a magazine. Even better, employment provides it.

It’s a bachelor’s dream – fancy pad, electronic entry, floor to ceiling windows, sunsets and sunrise, the view of the city. I am going to miss it. I really am. A man at age 27 doesn’t often have such a place, but it’s time that I focus on what I’m doing, and life isn’t about what you’re willing to get, it’s about what you’re willing to sacrifice for what you want.

I want to live like this again, and I will. But first, I have to let it go – flying from the 15th story in Baltimore, I may swing down before I swing up, but promise I’ll be back for this lifestyle soon.

Fear: “I can’t downsize, what about my favorite ______. I’ll have to give it up “

Yeah, that’s me a year ago – going from a 1200 sq ft wonder apartment to anything less was a pride fight. Now I realize, it’s not about the things, it’s about the dreams, the goals, and changing people around me for the better. The house is just a resting place.


Creating a Business from Your Skills

There’s something fun about doing things that you want to do versus what you have to. But when you create your business, those lines cross. Work and play become mixed, and although it’s often good to do what you love, it does present a challenge.

When is work off, and when is play on?When is it about money that you need to survive, and when is it about doing some good in the world?

The benefit for me isn’t in success, it’s in failure. Jim Carrey said it best (at 11:20) in a speech at the 2014 MUM Graduation.  If I can fail at what I don’t love, why not try at something I do? It goes back to failure, but I also think it’s important to recognize that successful entrepreneurs build a service to others by recognizing pain points, demands and needs. That means you have to listen, to learn and to grow with things you’re good at. Taking talents and making money from them is something you can learn to do.

I started doing graphics and coaching at a measly $20 an hour. Now I can live off of those two operations. Do I get $700 per month in extra spending and $500 in saving? No. But since my rate is up, I can work less and make enough to live, giving me plenty of time to create other side-streams from my skills.



If you don’t have mentors, you’re doing something wrong. Imagine you have a key to a door, and behind the door is a ton of information, know-how, advice, and input – all it takes is you walking to the door. Make the phone call, send the email – there’s no one that you can’t reach, and those with genuine interest in a subject can always find those that have knowledge willing to share it.

Mentors do a few big things for me. Most notably, they help reassure a good decision. There’s countless bad decisions that I need to make, that’s where I learn, but when I have a good one, they are quick to say – “Dude, I love it. Go try it.”

Secondly, it’s valuable to get around success; to smell it, meet its friends, and partake it its understanding. Success begets success.  Best of all, when they say that they’ve seen similar challenges and turned out OK, it gives me just the push I need to climb over the hurdle.

I notice their demeanor, their way of speaking, what they wear, what they care about, and how they address problems. It’s a lot different from how a 27 year old would, and that’s been key to my development.

Key: Never lie, take without giving, or fail to honor what they offer you. Thank you is often enough, depending on your closeness, but keep in mind how valuable it is and look to reciprocate as much as you can (not always monetarily).



Some would associate this as a luxury, but to me working hard physically is a requirement of my success. In order for me to get a better sense of self, a better understanding of pushing through limits, and a good sense of the impact of what I tell myself, I run, I lift, and I play soccer or other sports. I’m good at all of them, but it’s not from talent, it’s from putting in hours.

That’s the same concept with business. Put in the hours. Work hard, get past what you think you can do and kill your limit. It’s partly about being healthy too- if I’m not healthy, I can’t give my best, and if I can’t give my best, I might as well rest completely.


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