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Is a Flexible Work Environment Right For You?

by Robert Dickie III November 28, 2017

The gig economy in the U.S. is big and getting bigger. Freelance workers comprise 34% of the workforce, and that number could reach 43% by 2020. As on-demand businesses such as Uber, Lyft, and TaskRabbit offer people the opportunity to create their own schedules and work on their own terms, people have flocked to gig jobs as their side hustles or full-time employment. Freelance contractors are gigging in other industries as well, including writing, software development, and web design.

As the gig economy has grown, so has the demand for flexible work arrangements. Technology has made it possible to earn from home without sacrificing career advancement. Thanks to platforms such as Google Hangouts, GoToMeeting, and Slack, you can be in touch with colleagues throughout the day while maintaining your own schedule and creating the type of work-life balance that works for you.

Some people begin freelancing to supplement their full-time income. But once they see how much they can earn on their own, they crave more autonomy and freedom, and go all-in with gig work. Seventy-nine percent of freelancers who participated in a Freelancers Union survey said they joined the gig economy by choice rather than necessity, and half said they would not return to a traditional work set-up for any amount of money.

Employers love flexible work arrangements, too. Despite high-profile instances of CEOs calling their remote workers back into the office, as Marissa Mayer did at Yahoo, many bosses are happy to allow employees to work on their own terms as long as they get their jobs done. Having employees work outside the office lowers the company’s overhead. When remote employees and freelancers are self-motivated, bosses don’t have to micro-manage them, so they have more time to focus on big-picture pursuits. Everybody wins.

ROWE Your Way to Job Flexibility

In corporate America, there’s a growing trend toward Results Only Work Environments (ROWE). That’s the type of environment we strive for at Crown as well. I don’t want to resort to draconian policies such as forcing people to punch time clocks and watching to make sure they don’t go a minute over their lunch breaks. Such management tactics are dispiriting, and they hinder innovation and productivity.

We don’t monitor how much time people spend in the office; we just look at their results and the impact they’re having on the team. Generally speaking, I know who comes in early and who shows up late, but I judge performance based on output rather than time spent in the office. If someone starts to slack, I’ll meet with them to talk through any issues they’re having. But overall, operating with a ROWE mindset allows us to drive results without sacrificing our autonomy.

Successful ROWE teams enjoy high levels of trust among one another. Employees trust that they won’t be penalized for leaving work early for a doctor’s appointment or to pick up their kids from school. Managers trust that workers will finish their projects by deadline even if they’re working on unconventional schedules. The arrangement affords people more latitude, which decreases job stress and empowers everyone to achieve greater results. This is not your grandfather’s 9-to-5 economy anymore.

Of course, with autonomy comes increased responsibility and an expectation that you’ll deliver. I’m not interested in whether someone was in their chair from 9 to 5 today. I only care about what they produced. “I intended to get this done but I got sidetracked,” is not acceptable. I don’t manage by the clock or by intention. I manage according to what you put forward for the organization.

Work-Life Integration

One of the biggest draws to ROWEs or freelancing is the promise of work-life balance — or as I like to call it, work-life integration. In the old days, you left work at 5 p.m., and that was it until the next morning. But smartphones and laptops allow us to work anytime, anywhere. Integrating our work and personal responsibilities in a balanced way is critical to making a flexible job work. That’s why I advocate building a career around your passions.

When you’re working from home, chances are your work and personal life will blend together. You’ll chat with clients after getting the kids off to school, write up a report as they do their homework, and answer emails after you’ve put them to bed.

If you’re going to blend these different spheres, yo

You’d better love the work you do and the people with whom you do it. I don’t feel like I’m coming to work every day because my work is an extension of who I am. It fulfills and energizes me in all aspects of my life.

Who Should (and Shouldn’t) Work From Home

When people first consider flexible work arrangements, they focus on the positives. They envision spending more time with their families, hitting the gym regularly, and earning more money. After all, they’ll be happier and more productive working on their own terms. Why wouldn’t their output skyrocket?

But working from home isn’t for everyone. It requires a certain amount of fortitude and dedication, and some employees find that work-life integration is harder to achieve than they expected. It’s easy to become disorganized and overwhelmed as a remote worker, and some people realize they were happier going into the office after all.

In my experience, there are three key traits needed for flexible work success. You must be:

A Self-Starter

If you need someone looking over your shoulder and holding you accountable, a ROWE will be a disaster for you. I’ve seen fantastic workers flounder in a flexible work environment because they relied on regular feedback and encouragement to motivate them. Without external accountability, they struggled to stay on task. The gig economy demands that you be a self-starter. You have to be internally motivated to pursue new goals, meet deadlines, and continually level up in your work.


I said earlier that ROWEs foster trust between managers and employees. But they also require that workers trust themselves. While you’ll often be able to ask your boss or client for input on a challenging issue, sometimes you’ll have to make judgement calls on your own. You must be confident enough to make decisions and trust that you did the right thing. Getting hung up on questions and problems will derail your productivity and cause your flexible work arrangement to collapse.


You need discipline to get things done, especially when working from home. When distractions arise, you must remain focused on your goal. Sometimes that means telling your spouse you can’t talk or asking your kids to wait a few hours until you can play. It also means denying yourself the impulse to slack off or procrastinate. Not everyone can do that outside the office (they can’t always do it in the office, either), and you must have the self-awareness to recognize your limits before committing to a freelance or flexible work situation.

Career success ultimately comes down to knowing yourself. Autonomous work environments sound fantastic, and they are, for the right people. But if you know that you need more structure to be productive, don’t fight your nature. All of us are striving toward our own versions of success, and no two paths are the same. Whether you work in a managed office or a remote location, what matters is that your environment gives you the support you need to achieve your goals.

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