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11 Life Lessons that 4 Years of Entrepreneurship Has Taught Me

A stream of consciousness turned listicle.

November 2018 marks my 4th full year of entrepreneurship.

48 months of evaluating and adjusting my own performance.

104 pay periods since I’ve relied on someone else to make a paycheck.

208 weeks without really caring about whether or not it was Friday.

1,460 days that “calling out sick” wasn’t really an option.

35,040 hours of always being ‘on’.

2,102,400 minutes of truly being dedicated to a vision of myself and a company.

Cue the cast of Rent.

Just as I aspire to Grow my Business, I aspire to grow as an individual. This time in my life has forced me to mentally and physically push myself into places I’ve never explored and into constant reflection and self-evaluation. The great thing is, the lessons life can teach are endless and my time as an entrepreneur has seemed to speed up the process.

Many business owners, freelancers, entrepreneurs — you name it — are obsessed with the self-improvement culture. I challenge you to find one who hasn’t read Stephen Covey, Tony Robbins or had a small obsession with Gary Vaynerchuk at one point. It makes sense though: a business starts with a person, and for that business to grow, that person must grow as well.

The thing is, we are all just humans out here trying to do whatever we do better.

Or maybe not, and maybe you’re completely content with exactly where you are in your life and have no intention of ever growing or changing. If that’s the case this article is definitely not for you.

I’ll give you a moment.

Now if you’re still reading this there’s a chance you’re looking for one thing that might help improve your current circumstance. My time building my business has forced me to put a microscope on how I approach every single day.

I’m constantly implementing ways to optimize every aspect of my life whether it be my health, work ethic, or how I spend my money. Why? Because if I want my business to grow I believe I must grow as a person and optimizing these and other aspects of my life will help me do exactly that.

So for this anniversary, I figured I’d list out some of the lessons I’ve learned, the hacks I’ve discovered, and mantras I’ve adopted that have helped me… you know…survive. I don’t have all the answers, and my way is far from perfect but if you can find one thing in this article that you might be able to apply into your own life, then my time spent writing it was well worth it.

Oh, and if you can avoid making any mistakes by learning from mine, then my mistakes were worth it, too.

PS, this list is in no particular order, this is literally a stream of consciousness.

There is nothing that will grow you and your business more than the ability to say yes.

This is probably the trickiest thing I’ve learned over the last few years because there is a big difference between believing in yourself and faking it until you make it.

In my experience, in the beginning stages of growing your business you have to have the audacity to say yes to any opportunity that even vaguely resembles what you plan to do in the future. By doing this, you’ll learn to develop processes, sharpen your skills, and teach yourself problem solving and critical thinking. You have to be smart about it though, if you hurt someone’s business or break their trust you will officially lose them forever and damage one of your most valuable assets, your reputation.

Evaluate your resources, current skillset, and the speed at which you can typically learn and implement a new skill. Are sum of these three qualities enough to adequately execute the opportunity presented?

This takes a lot of self-awareness but once you develop that relationship with yourself, you can really capitalize on more opportunities that come your way.

When you develop enough of a portfolio, no one asks where you went to college.

The fact that I never went to a traditional, 4-year university was always a pain point for me. I guess not having a college validate my intelligence was a major source of insecurity. Because I never had that experience and it was held in such high regard by my peers I thought that it would be a massive barrier to my success when I jumped into the business world. Truth be told, it definitely was a barrier, but not a huge one.

This is kind of where the Personal Brand thing comes into play. If you haven’t figured it out yet, a personal brand isn’t just for travel bloggers or fitness models — it can help you, too (yes, you, reader). Developing yours may help acquire a new client, or land a new job. You might not get the interview from your LinkedIn profile, but when you submit your resume and they look you up , your digital presence will likely play a major role in the recruiters decision whether they admit it or not.

I’ve made it a point to share content from projects my team and I were working on, case studies, ideas, themed around was currently trying to gain a connection with — and guess what? It works. Either the content associated with my name helps generate a lead, or my experience is so well rounded that I can knock down any strategic question that comes my way when I’m face to face with a decision maker.

I’m not saying that you should ditch the idea of getting a degree or that it’s meaningless, all I’m saying is that if you produce good results, there’s a good chance other people will want those results for themselves, too.

Gratitude practices still sound corny, but they’re definitely necessary.

I would be lying to you if I told you that every moment of the last 4 years was all sunshine and selfies, but it’s not. Shit gets hard. I’ve lost clients, lost friends, family, dealt with my version of anxiety, depression, identity crisis — you name it. I don’t ignore these feelings by any means, however, I’ve found ways to focus my attention on the things that are going right in my life. The mere shift of your focus unlocks a completely different mindset toward whatever you’re dealing with and truly does help you feel happier, thus more productive.

There is always something we can be thankful for — a roof over our head, a meal, a conversation with an old friend — getting the seat at the coffee shop next to the outlet when your laptop is running low on power. Honestly, if you can appreciate the little perks of the day, those big goals you’re trying to accomplish will come a lot easier.

Use this gratitude practice from The 5 Minute Journal every day, and I promise you it’ll improve your life and how you look at it.


I didn’t maximize my opportunity being a writer for

When I began writing business related content, I was fortunate enough to have some of it published on In fact, a few of the videos we were producing at the time were also featured in the publication but after over a dozen of each and in that time it did not directly produce any leads.

When I say directly, I mean no one contacted me saying “I saw your article and I wanted to talk to you”.

Now looking back at what I was able to get published, I realize that I may have wasted that opportunity because I was fixated on writing content on self-improvement rather than more business related content. Additionally, the tone of my pieces were filled somewhat with angst, rather than the positive tone they generally like to publish.

I didn’t respect the platform I was given. I didn’t take the time to understand my audience. I didn’t write with any goal of growing my business, I used it as a way to feed my ego. Fuck.

And as a result, I was dropped as a contributor and didn’t get to reap the benefits of being published on a very widely distributed publication.

But hey, I still really like the fact that this one is live.

Instagram is a f*cking trap.

Instagram has been a tricky platform to navigate over the last few years. Frankly, I’ve had to constantly audit the time I’ve spent on the platform which I spend about 2.25 hours on average per day on (according to their new ‘Your Activity’ feature). How much of the time is self-serving and how much of the time is spent actually growing the brand equity of my business? Who knows. All I know is that when I took 30 days off of social media, there was a dramatic decrease in business inquiries.

PROS: the stupid thing has helped nurture some pretty incredible friendships and is also the #1 way to communicate my brand. Think about it; when you’re looking someone up what do you do? It’s no longer “are they on Facebook” it’s “what’s their Instagram”. You don’t even Google your tinder dates anymore.

CONS: Instagram completely ruins your creativity and productivity, makes you believe you have more friends than you actually do and sets unrealistic expectations for life, beauty, and happiness.

No resolution or advice here. Like I said: it’s a fucking trap.

Eventually, you will have to make the decision between the progress of your life and someone close to you.

During one of the interviews on my podcast, the guest had a heavy statement. She said, “You can’t heal yourself from trauma if you’re always surrounded by it.”


Sometimes people don’t heal as fast as you do. Sometimes they don't’ have the same desire to grow the way you want to grow, and sometimes they may not understand your need to do so. You can still love them, but sometimes it might have to be from a distance. Just trust me on this one.

Listening to music that does not contain lyrics while sitting down helps me get into flow better than almost anything else.

In my line of work, I’m in front of a laptop pretty often. Some days are harder than others complete a task as simple as writing a consultation email or knocking out a to-do list but the one thing that never fails to get me into flow is to listen to music that does not contain any lyrics. This means that even versions of a song that do not contain the vocals (like a piano cover) should not be on this playlist. I typically get really distracted in lyrics and vocal melodies.

Of course, everyone is different but let me share a couple Spotify playlists with you that really get me focused:

  1. Mellow Beats
  2. Lo-Fi Beats
  3. The Piano Bar

I’m usually at my computer using a standup desk (which is incredible by the way) but if I’m writing or working on a pitch deck I work best while sitting down. I think the posture tells my mind that it’s time to get focused.

Always search for promo codes at checkout.

When you’re starting your business, or if you are currently running lean there’s a chance you’ll need to spend your money wisely within the business and within your personal life.

I recently needed new jeans. I was sporting the same pair of PacSun skinnies for like 6 months and changed them out with one other pair if I needed to… you know, avoid anyone noticing I was wearing the same pair of jeans every day. I went to the store, and even though it was buy-one-get-one-half-off, I couldn’t really get into the pair I was trying out (pun intended).

I went home later that night and searched online for my exact pair of jeans but in different washes (stacked-skinny if you’re wondering). Not only did they have a better buy one get one free offer, but at checkout, I thought — what other discounts could I get? I searched online for a checkout code and I found one for an additional 20% off. I ended up getting 4 pairs of jeans for $75. That’s just hard to do.

This sparked a habit of always Googling a promo code for any online purchase I make. It doesn’t always work, but I’ve saved at least $3,200 since that purchase by searching for promo codes.

If you want to grow, hang out with people who have better habits.

Since my jump into the entrepreneur life, I’ve realized that the variable of success relies heavily on the habits you take on. This can be anything from lifestyle, to how you well you nurture your sales-pipeline.

One of the aspects of my life I’ve been adamant about improving is my physical health.

When I started out in 2014, I went to a really weird depressive state. I had just gotten fired from my job, found out my then-girlfriend was cheating on me and the state of the business at the time left my then-business partner and longtime friend and I estranged. This eventually leads to me coping with a few glasses of Jameson every night, late night runs (or drunken walks, rather) to Wienerschnitzel, and an extra 35 pounds on my ‘acceptable’ body weight.

There were some obvious changes I made to my overall diet and lifestyle that I made which gave me some immediate, noticeable results, however, I realized that I kept fluctuating back and forth. I couldn’t figure out why until I made a conscious decision to spend more time with people who had healthier habits.

And that was it. The presence of other people who were doing the things I wanted to do naturally led me to maintain the habits I found to be productive in my own life.

This idea can apply to anything. If you want to spend your Saturdays working hard, find people that will do it with you. If you want to grow in your faith, surround yourself with people who have the religious practices you believe in. Close proximity to those who have already accomplished the things you wish to accomplish greatly improves the probability of you doing it, too.

You have to find someone to keep you accountable.

There is a pretty big difference between finding a mentor and finding someone who will keep you accountable. By definition, a mentor is simply an advisor, but won’t necessarily make sure you follow through.

My recommendation is call up one of your friends who will help you keep track of your goals and tasks, and do a check-in every month to make sure you’re still on track. This doesn’t have to be a long drawn out thing, but the reason I’m suggesting this is because it’s easy to start justifying why you didn’t cross anything off of your to-do list.

I personally have a few in my own life. I have a controller who helps me keep my finances in order, an friend who’s experienced in sales who helps me maintain and track my sales goals, and I regularly attend scheduled group classes for exercise to make sure I show up…and actually work out.

And look, I don’t want to take any power away from you. Yes, you can probably do everything yourself — but you’ll probably do it better with someone to help you stay focused.

Aim for impact over impressions.

The most common question I get in regard to developing a personal brand or business is “how do I grow engagement”, and recently this is followed very closely by “how do I make sure my content gets seen despite Instagram’s algorithm”. The thing is, I truly believe that if you are creating any type of content or building anything at all, it’s essential to make the impact of your “thing” the key performance indicator, not how many people it reaches.

When you aim for impact, your return on investment will be much greater because your message is so much clearer. Often when something is directed to the masses, the message becomes watered down and less meaningful.

The next time you launch a piece of content, think of one person you’re creating it for. What would you say to them, how would you say it? Where would you say it? By being meticulous about your delivery, you greatly increase your chances of creating the emotion that will produce the desired conversion.

And wouldn’t you rather have someone take a real action rather than just double tapping?

As I finished that last point I realized that I could literally continue writing an entire book on the things that I’ve learned in the last 4 years, and I decided I should probably just stop and create a new article that is more concise.

But before I wrap this up, my final point is always to be eager to learn.

The number one way we can all continue to grow as individuals and as a community is by learning from one another.

If you enjoyed this article, please click the clapping hands. It helps others see it and I’d really appreciate it.

11 Life Lessons that 4 Years of Entrepreneurship Has Taught Me was originally published in The Ascent on Medium, where people are continuing the conversation by highlighting and responding to this story.

This post first appeared on The Ascent, please read the originial post: here

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11 Life Lessons that 4 Years of Entrepreneurship Has Taught Me


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