The Lie We Tell Ourselves as Entrepreneurs: “It’s Just Me.”

Zachary M. Cochran
13 min readFeb 21, 2020
Photo by Hunters Race on Unsplash

The Entrepreneur. He stands highly elevated in American culture. He is the “pull-yourself-up-by-your-bootstraps” poster child. Perhaps he’s why many of us became entrepreneurs in the first place. It sounds so simple — stick it to The Man, start your own company, and start raking in the cold, hard cash.

The reality is, of course, far more complex, not helped by the fact that we now live in a hyperconnected world. This hyper-connectivity means that the systems of 20 years ago are now effectively 100 years out of date. We’re developing and advancing too fast. Our systems aren’t keeping up with our business opportunities, so unless you’re a trained salesperson who has developed intense personal discipline and pours his or her life into his work, it’s hard to handle the problems of this new hyper-connected world.

What problems are these, exactly? Let me offer a couple.

1. You have so much access to media, which content is the most valuable to consume? We need a “nutrition guide” for our media consumption, so that we’re gaining valuable insights from the books, audiobooks, podcasts, articles, and other media we read, listen to, and watch. Especially when we’re looking for wisdom about how to live well in our particular context in life (as a small business owner, advancing employee, parent, etc.). We’re used to having immediate access to all the “right answers” on Google, but the tough cases we face in our business builds require us to train and develop wisdom that is much harder to find in a search online. This is the world of career direction and why I started a company to help young professionals go from confused & aimless to having clarity, focus, and support engaging in a career they find fulfilling and well-matched for who they are and what they need.

2. How do you maintain your gigantic relational network? Sending content updates to your 1000+ followers and “friends” or connections on Facebook and LinkedIn is a part of an effective strategy, sure, but not sufficient. What about mailing lists? What about keeping everyone’s contact information up to date? There is a massive competitive advantage in being a hub to your network, the gatekeeper to so many important relationships, but how do you effectively manage a massive network once you’ve built it? It is challenging, with no easy answers.

I wrote an article on “systems debts” — a concept I coined after reading about the concept of “technical debt,” which I applied to my own context. In short, systems debts are those daisy-chained systems failures that make it impossible to achieve optimal productivity. I list several examples in the article. As one example: I am late to my meeting, because I had to iron my shirt and I couldn’t find the iron, because the home was a mess, it was dark and my spouse was asleep and I didn’t want to wake them, and because I committed to back-to-back networking events and was short on sleep and hadn’t cleaned up the room yet.

As a small business owner, some of the bigger problems we have revolve around the three hats we have to wear: the entrepreneur hat, the “technician” hat, and the manager hat. Pulling from Michael Gerber’s The E Myth, these three roles are required for any successful business, and that means as a one-person business, you have to do all three well in relatively equal proportions. The entrepreneur looks to the future and does all the business development. Without this, the business won’t grow, and won’t have a vision of where you’re headed. The “technician” is the “working in your business” part of it, whatever that work is. You won’t get far if you don’t have actual paying work or the time to do that actual paying work. This happens in the present. The manager is the role you play when you keep on top of all the administrative aspects of your work. A manager looks to the past and learns from it to understand how to arrange things effectively. For those familiar with the DISC assessment, the high I’s (and high Ds) do well at the entrepreneur hat. The high S’s do well at the manager hat. The high C’s (and high Ds) do well at the technician hat. To do well running your company, you have to do three separate jobs. It is rare that a solopreneur that can handle all areas of his or her business well.

Like many early-stage entrepreneurs, my particular challenge and focus right now is in growing revenue. To do that, I need to tap into my High I side: meeting people, having conversations, following up, and turning that activity into real clients. There is a technical part of this process as well — perhaps it will sound familiar to you if you take a more traditional approach to your business development:

· Getting and responding to emails in a timely manner

· Keeping abreast of all the events you could be going to, being selective about the ones you purchase tickets for and/or put on your calendar, and actually going

· Taking business cards and converting them to a digital format so they are easily accessible when you’re running around, as so much of our businesses are managed off of our phones

And for those who have learned to automate and scale their approach:

· Using a CRM

· Using mailing lists

· Scheduling social media posts with tools like Hootsuite and Buffer

· Perhaps even using automation on social networks like LinkedIn to drive views and engagement

If your problem is that simple, great! There are a lot of solutions and pro-tips here:

· Use a virtual assistant from a site like Fiverr.com

· Use a business card scanner app, like ABBYY or CamCard

· Use a CRM like Pipedrive, Zoho, or Salesforce

That said, the core problem isn’t usually one that can be solved with a quick fix or a technology. The core problems go much deeper.

Often, our problem is that we don’t know where to spend our time, because we don’t know the best problem to be working on (so we’re running around, doing the shiny object stuff, or just having a scattershot approach to our productivity).

Other times, we’re hitting roadblocks because of bad workflow habits — never filing anything can quickly create a nightmarish desk with an inability to be efficient (those ugly systems debts again). But maybe we developed these bad habits due to an undiagnosed underlying cause, such as: whenever we interact with emotional content, we shut down and put it away for another time. Chronically, this lack of engagement with emotionally difficult information means that we have created an invincible monster in our office that keeps us captive and stops us from doing our most productive work and living at our potential.

Perhaps you played video games as a kid (or as an adult, no judgment). Were you the kind of gamer who ran around every square inch of the map, in hopes that you’d find the super rare treasure that the devs hid in the game? Usually, this was a waste of time, but like a child on sugar, you ran around seeking that high from finding the crate with the legendary loot that you might find very infrequently in a game (I’m looking at you, Borderlands). Couple that with your teachers’ and parents’ requirement that you be thorough, and now, even when it doesn’t benefit you at all to be thorough, you can’t break free of your programming (or that search for the high you got when thoroughness paid off). So, you spend way too much time on low-value tasks, in part because you don’t know what your high value tasks are, and in part because you think that looking anywhere is better than looking nowhere, so you read every email that comes in or talk with every person who will listen to you at a networking event, and you don’t stop to refocus on what is most important, or build a roadmap to get yourself there. You don’t know when things are good enough to move on.

Another big productivity thief for entrepreneurs is optimism. Yes, you read that right. We’re big on vision, but we can quickly fall into the trap of believing that we actually live in this fantastical, ideal world we’ve created in our minds, where we will respond to every single email in our inbox (despite having never accomplished this before) simply because today we have set our intention and we will do what we decided to do. Yet again, we’ve fallen into the planning fallacy, a mindset that everything will take way less time than we think it will (usually on the order of 4x less). So, we set on our calendar a 1-hour meeting, believing that it will only take one hour of our time, and yet we fail to account for the prep time, travel time, time spent waiting for other people, time spent when the meeting goes long, time traveling to our next destination, and time spent on processing the conversation and following up on what was decided. That one-hour meeting actually cost you your entire morning. One key here is to be selective as to which meetings you attend, but another key is to account for all the extra stuff that adds to the “time cost” of any commitment.

Another core trap we fall into is that we have a million and one inputs: notifications, news updates, social media newsfeeds, texts, calls, and many other interruptions to our day. How often do we (or can we!?) shut off all these inputs (and I mean, all) and do some deep work (to borrow a term from Cal Newport). Deep work is the work we do that creates real value, because we are creating connections where there were none before or producing new things (material or intangible) that wouldn’t have existed apart from our labor. This is where the real value is, and we don’t give ourselves the time to do this unless we shut out the noise and set up some boundaries and say “no” to everything else for a while when we focus on our project.

Another big challenge is the way we fall into a victim mindset. We blame our failures on others or just don’t take personal responsibility for our mistakes. “The train was late” and “I got caught in traffic” are some of the smaller, more socially acceptable ones (as long as they’re not the same excuse every time). “He didn’t get back to me” and “I didn’t see your message” (read: don’t blame me) are other deflections. Any time we do this, we’re living “below the line” of accountability (a concept discussed in a fantastic book, The Oz Principle). When we’re busy making excuses, we’re not set up for success in our relationships — and we’re setting an unfortunate precedent that means a bigger and bigger hit to our reputations over time. Sometimes, a simple, “I’m sorry, I was late” means a lot more to the person you’ve made wait than “well my dog got sick” or any number of other imaginable excuses. As entrepreneurs, we have to deal in reality — living below the line doesn’t suit us and won’t help us build and grow successful, profitable businesses.

Granted, not all of these issues are our faults. The world we live in today is complex, and we are not usually set up for easy success. To use a simple example, our iPhones (or other smartphones) don’t have the built-in functionality of a fully customizable CRM, despite the fact that we live in a world today with access to hundreds or thousands of people, which makes such a system necessary. Since it’s not built-in, we have to find, learn, and buy third-party CRM apps — assuming that we’ve realized that a thing called a “CRM” exists and we know that will solve the issue we’re facing.

It’s rare that people will give you a heads up that these underlying problems (the ones I discussed above) are the core problems that you’ll face in your business. Perhaps you’ll hear about a few of these common issues in your entrepreneurship classes in college, but that’s only if you took entrepreneurship (which most of us didn’t), and even then, you’re faced with the gap between classroom instruction and “the real world,” where the mundane but very real challenges that small business owners face are the ones that threaten their businesses. More entrepreneurs are brought down by mosquitoes than dragons. A lot of these issues don’t hit our radars, because they’re based on fundamentals, meaning, fundamentally, how I live as a person and how I was raised does a lot to set me up for success, or to create a lot of very difficult-to-overcome roadblocks. Or roadblocks are really the wrong analogy, because that assumes we can see these problems clearly and have time to slow down before we crash into them. Landmines is the better analogy, because we don’t usually see the bomb we’re walking on until it blows up on us and causes damage that may or may not be avoidable. (Yes, I’m aware that relating entrepreneurship to guerilla warfare is not a fair comparison in its full extent, but entrepreneurship does feel more like feeling your way around blindly and spending time bunkering in the trenches vs. the big smiley publicity stunts we see a lot of “successful” entrepreneurs doing on social media.)

One final landmine for this article. Sometimes, we’ve done hard introspective and analytical work and are aware that all these things are challenges: that disheveled stack of papers on our desk, the untouched boxes of business cards we’re not doing anything with, the emails that number in the thousands, many of which are still unread, and an overwhelming feeling (bordering on depression, at times) that we’re being ineffective, chasing the shiny object, and we’re on a road to failure. On top of this, sometimes, there are real, diagnosable mental health challenges that we need counseling or medication to fix. The problem isn’t any of these challenges — we can learn and tackle and solve any one of them. We can even, over time, and with the right support, solve all of them. But we stay stuck when we tell ourselves: “it’s just me.”

“It’s just me.”

Does this small accusatory voice sound familiar? It goes like this:

Everyone else at the networking event looks like they have it all together. They’re in conversations, they’re smiling, they’re networking. Am I the only one who hasn’t figured out how to convert these conversations into sales?

I got an email back from that guy almost immediately. I know I have emails from last week — heck last month! — that I haven’t dealt with yet. Am I the only person who can’t respond to their emails in a timely manner?

I have been sitting down at my desk for an hour and I’ve just been surfing the web — and I’m supposed to be working. I don’t know what I need to be working on, I feel overwhelmed, and I feel like I’m running out of time and I’m missing something important. What will happen when people realize that I am undisciplined, irresponsible, and unresponsive? I won’t have any clients and my children will starve.

That voice in our heads gets dramatic. Our feelings can be so strong and so intense, especially after a crazy week and a night or two of not enough sleep. If we could raise our hands, be vulnerable, express that we need help and that we don’t have everything figured out, and that we’d like to talk with some other “real” people about this (vs. the perfect head shots that they appear to be on LinkedIn), wouldn’t that be amazing?

People say that it gets lonely as an entrepreneur. This is not because we don’t talk with other people, we have to do that. Sometimes, it’s lonely because we don’t feel understood in our challenges, but most of the time, it’s because we don’t have anyone who we can confide in and share our real frustrations with (because we can’t always vent to our friends or share our insecurities and fears with our family). We need a group of peers who understands what it’s really like as an entrepreneur — but not just a therapy group (though that dynamic can be quite helpful), but a group who can offer real solutions and benefit us as a moral support team to boot. But this only happens when we surround ourselves with others who are willing to admit: “I thought I was the only one who was dealing with that, too.”

If you’re a small business owner, you have 0–5 employees, you have under $1M in annual revenue, and you have access to the Internet, you should reach out to me about this new entrepreneurs peer group I’m starting as a partner and facilitator with Clark Leadership Group. We are looking for 8–10 Millennial-aged entrepreneurs (though we’re not age-exclusive) and bringing them together online twice a month for 90 minutes to process through the issues that each group member is facing in his or her business. Entrance into this peer group requires that you are a learner. Learners are people who can put into practice what is discussed; otherwise, groups of this sort carry little value for you. If you are interested in engaging regularly with a group of your peers to confidentially and confidently share your biggest issues and offer your insights to the group, you will be one of the lucky few entrepreneurs who benefits from the collective wisdom of an entrepreneur peer group. It’s also something you can write off as a business expense, so there’s no excuse not to invest in yourself and work “on your business.”

Reach out to me if you want to learn more, or if you’re ready to experience the group. We’re building our founding members base in this industry-exclusive group, so before another person in your industry takes your spot, let us know that you’re interested. We’re planning to start meeting this April 2020 and run the group indefinitely — though we’ll start a second group when the first closes and is full.

Email me today to learn more.

The bottom line? Entrepreneurs…we need more support than we’re getting. Reach out to your peers. They need you as much as you need them.

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Whether or not you decide to join an entrepreneurial peer group, you can be sure that you are not alone. These challenges are common to all of us, and if you don’t already have an entrepreneur friend you can talk with about them, you should figure that out. In the event you need to talk with someone one-on-one and want help being coached through your challenges without opening yourself up to an entire group, you may be a candidate for 1:1 coaching, which I offer through my company, Cochran Coaching LLC. Feel free to reach out if that’s you.

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Zachary M. Cochran

I think a lot + write about #careers #entrepreneurship #wisdom #productivity #grief #Christianity #NYC #parkour + more. To learn more, visit zacharycochran.com.