The Right Mental Attitude for Remote Entrepreneurs

By Alex Cruickshank on
The Right Mental Attitude for Remote Entrepreneurs

"I can't work in an office: I'd go postal within weeks."

Having been a remote-based entrepreneur for the past 20 years, you’d be surprised at how often people tell me that remote entrepreneurship just isn’t for them.

Since 1996, I’ve built a web publishing company that employed multiple remote workers, and I've written for some of the world’s most influential companies. I achieved all this while working from my home offices–first in the UK, and now in rural New Zealand.

This style of working suits me, but remote entrepreneurship isn’t for everyone. Beyond the obvious requirements (an internet connection, a business plan…) I’ve noticed that successful remote entrepreneurs share a set of personality traits that carry them through both the best of times and the worst of times.

If you’re toying with the idea of going remote, benchmark yourself against these commonalities before you pack up and hit the road.

Office Antics Hold Little Appeal

A couple of years ago, I gave a talk to a room full of entrepreneurs, developers, and recruiters about the pros and cons of working in remote teams. There were four of us on the panel. The other three panelists were running their own development companies.

What emerged during our talk were similarities in outlook, business strategy, and personality between every remote entrepreneur on the panel. My attitude, and my admission that I was effectively unemployable, were far from unique. All of us agreed that office-based working had never suited us.

Remote entrepreneurs enjoy their freedom and independence. They don't respond well to authority or to being ordered around. Nor do they appreciate manipulative behavior. In this respect, many of them are INTJ personality types.

They’re Skilled at Connecting With Others From Afar

Just because they have no time for office dynamics doesn’t mean remote-based entrepreneurs are shy when it comes to networking. On the contrary, they see networking as sensible behavior.

As part of any remote working strategy, you must stay in touch with your peers. Not just on social media, either. Remote entrepreneurs are skilled at connecting with others, often using any number of the following tactics:

  • Attending networking events, seminars, and conferences

  • Visiting clients in person

  • Meeting socially with people in similar or complementary lines of business

  • Participating in online forums

  • Building new relationships with their peers on social media

Staying connected is obviously a good way to pick up work. But remote entrepreneurs also know staying connected reduces FOMO—the fear of missing out on the “real” world of business. Never underestimate the value of interacting with other people, of bouncing ideas around and networking. It's the lifeblood of many remote businesses.


There are more lazy employees than lazy entrepreneurs, for the simple reason that lazy entrepreneurs don’t get paid.

They Aren’t “Hangers-On”

People become remote-based entrepreneurs for all sorts of reasons, but one that crops up repeatedly is a dislike of lazy coworkers. They don't tend to enjoy "coasting staff” or “hangers-on,” employees who take up desk space but contribute little.

True, not all office-based staff are like this. Most are hard-working and ethical. But there are more lazy employees than lazy entrepreneurs, for the simple reason that lazy entrepreneurs don't get paid. In fact, lazy people don't usually have the drive to become entrepreneurs in the first place.

It can take months or years for an employee's lack of work to be noticed and dealt with—and all the while, they're still being paid. But if remote entrepreneurs don't work hard, the effect on their income is immediate and dramatic.

When working in remote teams, there's nowhere for the lazy to hide. Remote-based entrepreneurs are proud to be judged by the work they produce—and they expect to be paid accordingly.

They’re Comfortable in the Face of Isolation and Solitude

“How can you work without people around you?” I've been asked. “That must be awful, like working in a cave.” It’s a good point. Solitude and loneliness are real issues for remote entrepreneurs, even those who maintain connections from a distance.

If you think isolation and solitude won't be a problem for you, think again. I've known colleagues who gave up full-time jobs to work remotely, and six months later they were back in the office, employed again. They couldn't handle the solitude.

I don’t mean to scare you, but in severe cases, loneliness can even lead to illness. As a web search for “depression remote workers” or “depressed freelancers” shows, depression is a real problem for remote workers. I've seen it happen to friends of mine.

Long-term remote entrepreneurs know how to balance work with pleasurable, sociable activities in order to offset this risk. They understand that they should never skimp on happiness and wellbeing.

They Enjoy Being Judged on the Quality of Their Work

No matter how charming you are as a remote entrepreneur, the quality of your work and reputation will determine whether you succeed or fail; it allows you to charge as much (or as little) as your work is worth.

That's a big incentive to produce high quality work every time.

That said, remote-based entrepreneurship is full of successes and failures. Perhaps because there's nobody to share the blame with, successful remote workers are often resilient enough to accept hard feedback and take responsibility for their mistakes. Long-term remote workers also have a knack for using their failures as lessons on how to improve the way they operate their business.

They Approach Time Management Very Differently

Remote entrepreneurs have to be good at time management. There's no fixed start or end to the working day. Their time is their own to manage as they see fit.

I have remote-working friends who work from early morning to early afternoon, then stop. Others start at lunchtime and go through until late in the evening. Some friends work normal office hours. Others work much less.

What they all have in common is inner drive and determination. They have the ability to ignore distractions and manage their time effectively. They don't need to be told to work. They know what has to be done, and they do it.

Above All Else, They’re Confident

The most important character trait of all is confidence. Successful remote entrepreneurs know they're good at what they do. They believe it firmly, because there’s nobody around to validate them. Like the original free-lance, remote workers can and must depend only on themselves.

There’s no getting around the fact that the remote life can be tough. If the thought of embodying any of the above characteristics makes you feel uncomfortable, remote-based entrepreneurship might not be for you.

Some people work best on their own, others work better in company. Just be sure you know where you stand before you hand in your resignation to start a remote business.

As a remote-based entrepreneur, you'll be performing without a safety net. If you fall, there will be nobody to catch you and it's going to hurt. But when you succeed, you'll feel as though you're soaring above the clouds. It's one of the best feelings in the world—and it's all yours.

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