EP09 – How to Navigate the Entrepreneurial Journey

How to Navigate the Entrepreneurial Journey

Choosing to become and Entrepreneur and going “all-in” as an entrepreneur is a path that very few of us follow.

There’s a simple reason behind why this is true: it’s bloody difficult!

Being an Entrepreneur means that you’re going to be making huge sacrifices in practically all aspects of your life in the hopes that eventually, some day, it will all pay off.

Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t. – Anonymous

The Reactions from Family and Friends

It’s not out of the ordinary for people to judge you for making the decision to become and Entrepreneur. I’ve learned this lesson and so have some of my closest entrepreneurial friends. Our very own Carter Johnson faced this head on early in his life with his family. When he told his family that he didn’t want to go out in search of a full-time job, instead opting to create his own, they constantly tried to stop him.

Carter’s family would send him job postings for the most random jobs that anyone could think of. His own parents sent him a the posting for a job opportunity at the local airport to be an air traffic controller! What!?

But it makes perfect sense when you dive deeper into why this was happening. People are conditioned to want to follow a system. From learning to crawl, walk and talk, to attending a great university and landing a comfortable 9-5 job, to getting married and having 2.5 kids, we’re all so used to following “the path”. So when someone wants to step outside of that path, it’s seen as disruptive.

I remember watching I’m Fine Thanks (not an affiliate link, I just love that documentary) and hearing one of the interviewees talk about a common question you’d hear as a child… “If all your friends jumped off a bridge, would you?” which is really just trying to deter you from doing something that everyone else is doing, yet when you grow up, that saying is completely reversed, it’s “Everyone else is jumping off that bridge, why aren’t you!?”

Now this transitions us to my experience with my family and friend when I made the leap to becoming a full-time entrepreneur. Back in 2012 I was working as a Senior Software Engineer and getting paid nearly 6 figures in a job that I really enjoyed. I loved the people I worked with and it seemed like I was a complete success. But I ended up handing in my two week notice to pursue my dreams, and that’s when I started to get the negative feedback.

It came from one of my co-workers who I looked up to and had developed a great friendship with. They saw the move I was making and their only reaction was to try as hard as they could to keep me from following through with the decision. They would tell me every day for two weeks what a terrible idea it was for me to quit my job, and that I was being reckless and stupid.

Can you imagine that? Someone that you’ve known for years, and who you look up to, telling you that you’re being an idiot. It’s really tough to just shrug that off.

Panic Attacks and a Visit to the Doctor

The whole decision to quit my job actually weighed so heavily on me that I ended up seeing my doctor. I was waking up in the middle of the night with my heart racing and beating irregularly, my palms sweating, my chest hurting with shortness of breath. It was scary. Thankfully my doctor said that it was just anxiety from this big life decision I had made and that I just needed to learn to relax and know that I wasn’t going to die!

Because for me, in that moment, when my heart was racing, I thought I was truly having some sort of cardiac episode and might need to call 911. That’s how powerful our minds are!

So once I was able to realize that it was just all in my head, I made a HUGE turn-around and I don’t think I’ve actually had that sensation ever again. I stuck to my guns and said, YES, this is my decision and this is my dream. Now is the best time for me to pursue my dreams, and no one else can take that away from me.

So if you’re in a similar situation. If you’re battling with your own feelings. If you think you’re making the wrong decision to pursue your dream to be an entrepreneur. Just know that you’re not alone. All of us went through that transition, all of us had to deal with the nay sayers, all of us had to deal with our own doubts.

It’s the strongest of us who push through all of the doubts to realize that we’re pursuing our dreams for a reason! I’d rather pursue my dream and fail, then never try. Because what’s the worst that can happen? If you fail, you can always try again using a different strategy. Entrepreneurs fail WAY more than they succeed. It’s just the name of the game.

Tweet: Most people will choose unhappiness over uncertainty. -Tim Ferriss in the 4-hour Work Week http://ctt.ec/2fy15+

Mastermind Groups

Naturally, you’ll want to know how to overcome this negative feedback you’re receiving from the nay sayers in your life. That’s where a very simple strategy comes into play. Stop hanging around the nay sayers and start hanging around with people who support you in your journey.

Easy to say, but how do you do it?

Well, you’re on your own for distancing yourself from the nay sayers. There’s not a whole lot of advice that I can give you that you don’t already know. Just don’t hang around with them any more!

The real question is how do spend more time with those who would support you? One amazing thing you can do is to join a group (or create one) of people that share your exact same goal. Seek out other entrepreneurs who understand who you are and what you do. Schedule a time (preferably once a week) to meet with those people (either in person or through a Google Hangout / Skype) and help support each other achieve your goals.

This is called a mastermind group.

I’ve been in a mastermind group with 3 of my entrepreneurial buddies for the past 2.5 years. We share our ups and downs with each other and provide help when anyone is stuck. Some of the biggest changes I’ve made in my business that have netted the biggest gains have come from suggestions in my mastermind group.

For example, the idea for how I could go about focusing on building my email list came from my mastermind group. A few days after that call my email list went from around 10 people a day signing up, to over 30. I tripled the growth of my email list, just from one 45 minute call.

You never know what will come from a mastermind group, but you know that it will almost always be amazing.

If you don’t know any entrepreneurs, then hop onto MeetUp.com and find people in your local area who are organizing in person meetings. Look for groups on Facebook that are centered around entrepreneurship, then get to know some of the members. There are SO many groups on social media that focus on the dream of entrepreneurship (not just Facebook), so this won’t be a problem for you. The trick will just be to find people that you actually ‘click’ with.

Setting Expectations

As excited as you may be to drop everything and pursue entrepreneurship, it’s important for you to set expectations.

I’ll lead with a sobering statistic. If you were to start your first business today, after a few years you’re more likely to fail than succeed.

As demoralizing as that is, there is a reason for it. It’s because entrepreneurship is not easy. If it was, everyone would own their own business and be millionaires! So I don’t want you to walk into this potentially new venture thinking that you’re going to rule the world. It’s important to keep a level head and embrace the fact that the next few years are going to be some of the most challenging of your life.

First place I would start is with your significant other. I think it’s pretty bloody important to have them truly understand what’s going to happen in your lives. Things will need change if your business is going to be successful. No more going out for dinner dates and movie trips and walks to the ice cream store. It’s time to hunker down and get the work done.

The reason why it’s so important to set expectations with your significant other is so that they can be a support system for you. Because you’re going to need a good support system; a strong foundation. I attribute my success to not only the fact that I’m driven so fiercely to learn and succeed, but because my fiancée has supported me through thick and thin. So if they’re not on board with your dream, then you’ve got two choices, change the dream or change the significant other!

Okay okay, don’t break up with the partner of your dreams just because they don’t see your vision for your life… but it’ll definitely make your journey more difficult if they aren’t behind you 100% during those first few “dark” years.

Having said that, what will really help your situation is having enough cash saved up before you go “all-in”. I personally had about 6-8 months of living expenses saved up when I quit my full-time job. In hindsight, I think that was a mistake. I wish I had saved more (perhaps about 12 months worth of living expenses), PLUS enough to cover business expenses!

Don’t make the same mistake I did and not account for the money that you’ll need to spend to start a business and RUN a business. Business expenses can add up, I believe I tend to spend about $2,000/month to keep my company running (and that doesn’t include paying my salary). So be sure to factor that into the equation. I believe my business could have grown at a much faster rate if I’d had more money to put into it every month.

Finally, if history has any say in your new venture, it’ll likely take more than 3 years before you really start to see any true success from your startup.

I know it seems like such a long time, but in my opinion working your buns off for 3-10 years to live the rest of your life like none of your friends would ever dream of living, is one hell of a good deal to me! Because those years that you’re working your buns off are going to be FUN years (for the most part).

How to Fund your Journey

As programmers we have one advantage that we can really leverage, and that’s our skills as programmers. If you’re willing to just keep on working your full-time job while you build your business on evenings and weekends, then so be it! You’re in a great spot and I’d say just keep on going until you would be able to replace your income with your side hustle.

But for most of us, that may not be the case. Maybe you’re absolutely fed up with your employer, or your urge to go full-time with your entrepreneurial journey is just too huge to ignore. Whatever the case may be, here’s a good tip to help ease the transition.

Go to entrepreneurial meetups.


Go to the aforementioned meetup.com website and find a gathering of entrepreneurs in your area. Then ATTEND those meetups! You’ll get two things from the events:

    1. You’ll meet some like-minded people and may be able to put them in your mastermind group
      You’ll likely have an almost unlimited source of contract opportunities
  • The vast majority of Entrepreneurs can’t code. And a heck of a lot of startups these days can’t function without a website. So chances are you’ll be one of the only ones in the room who has a coding background. Use that to your advantage.

    You’ll be able to land contracts that will help you to work part-time as a programmer and full-time as an entrepreneur yourself.

    It’s the route I went when I was building my business and saw that I was about to run out of cash!

    An even better tip would be to find a meetup of entrepreneurs who are in an accelerator or incubator program. Typically those businesses have the funding needed to bring on a programmer. I remember being at one of those events in Toronto, Canada and I felt like the prom king. Every company there was drooling over me and giving me their cards and trying to sell me on why I should work for their company.