Why Work Freedom Isn’t For Everyone

I sometimes get caught bragging about the freedom I have enjoyed since leaving my traditional salaried 9-to-5. From sitting on the porch with my coffee in the morning to taking a mid-day creativity break in the hot tub (with a beer should I be in the mood), I feel pretty lucky to have stumbled upon such a fulfilling work/life style.

Over the past few weeks I have become more acutely aware of how this lifestyle is interpreted by others, which has brought about acceptance that not everyone can grasp the concept correctly or handle the freedom that comes with it.

The two primary reactions:

  • I wish I could just walk away, followed by long complaint about my current job. 
  • That’s great, this is what I am doing to create fulfillment, followed by excited story about how I am investing in my own lifestyle.

Essentially, some folks look at my work freedom as freedom from work. They drool over the ability to do whatever they want all day. This is called retirement and is by no means the case for me or anyone else merging lifestyle into their work.

I have been wondering if there is a specific factor that creates this distinction or if the perspective alone can occur among any personality type and stands alone in determining success or failure when freedom is mixed with work.

This distinction between those who would relish being highly productive on their own terms and those who seem to need a boss, desk, and colleagues to produce the goods was clarified with a recent conversation.

I have a non-overachiever friend. She’s very bright, great with people, and does a great job for her employer. She’s more of a blue/yellow personality, focusing on relationships and big ideas than on tasks and details.

A few days ago she indicated she wanted to get together to discuss how I attained my current lifestyle in more detail and then went on to complain about how her current boss has anxiety about allowing her to work when it is best for her. Turns out her boss is a morning person and prefers to hold a brief status meeting in the morning to prioritize and then jump right in to getting those tasks completed.

For my friend who isn’t quite alive until 11 AM after her very strong coffee has kicked in, this doesn’t make sense. She looked at me as if I could talk some sense into her boss if given the opportunity.

That same day, as my friend was complaining about how much she has on her plate and how her boss and others just don’t understand how much work is entailed with her current projects, I encouraged her to set a day aside to catch up, even if it took all day.

Her response to this was that she has realized the value of work boundaries over the years (using her wise voice). She shared that a few weeks ago she had a project due on Monday with a few loose ends as of Friday at quitting time. Instead of finishing off the project over the weekend, she made the more sane choice of hanging out with her boyfriend and going to a ‘killer’ party. She looked at me as if I was super naive for suggesting that she spend extra time on her job than she has to.

I have had similar conversations and reactions from quite a few people over the past year. The 40-hour week ‘full-time’ work structure perpetuates a mentality that one should perform only up to that ceiling, which makes logical sense from a lot of viewpoints. However, it is the same people who refuse to work after 5 PM who are also complaining about the lack of flexibility within their jobs.

As someone who has overseen a large workforce, I can tell you that I only ever offered flexibility to folks who were clearly willing to work after 5 PM…or on Saturdays…or during the middle of their vacation time if needed. This level of commitment and dependability comes with leverage. Not only did I not want to lose these people, I also wanted and trusted them to work during their peak productivity hours. If loose ends existed at 5 PM and their deadline was looming, they stayed late, took work home, or came in early to finish up.

This is the mark of a professional-level team member, an overachiever. No longer just an employee, they often rise to the ranks of leadership or to management positions overseeing important projects. With those promotions comes greater self-determination, flexible work hours, and the potential for comp time after a major project.

I would propose that this also distinguishes those who can truly succeed within a work freedom arrangement, whether working remotely or for themselves.

Because the temptation to watch back-to-back episodes of Breaking Bad or sleep in until 10 AM is omnipresent and the work is highly variant, it takes a certain level of dedication to maintain a balance between highly productive effort and living life on your terms. Some days there is a lot to do and other days there is even more.

Work freedom is not about being lazy or indulgent. I would counter that I can be a whole lot lazier and indulgent within a strict 9-to-5. I can recall many employees who took multiple latte breaks during the day, chatted their work friends up for 20 minutes at a time at regular intervals, and who left every work distraction behind as they drove out of the parking lot at 4:59 PM.

One could argue that the 9-to-5 is truly the way to live it up. My conclusion is that those who don’t suffer from the overachiever gene would likely be miserable in a work freedom arrangement, as much as they think otherwise.

What do you think?

  1. Figuring out best practices for anyone transitioning from structure to freedom would definitely be interesting! I imagine the must-have ingredients would be determination and persistence. With those in hand, I would hope that anyone could create the best suited work/income arrangement for them. Thanks, Diana!

  2. (this is my third attempt (bah humbug!) Anyway …

    This was an impact-full message to anyone wanting to test the freedom workplace, and switch from their 9-5 grind. It takes tenacity and discipline. It’s not for the feint of heart.

    The way you ended this article by perfectly balancing the two realities was fabulous. Loved it!

  3. I would tend to agree with you, although I do wonder like Done By Forty if it’s possible for a person who isn’t a natural overachiever to adapt to a work freedom situation and be successful and, if so, what those steps would look like. Would certainly make for an interesting experiment.

  4. Agreed. My own experience as a self-admitted workaholic is that by fusing work with home, I personally can achieve more balance than within a 9 to 5 simply because I was away from home so many hours a week. Now at least my work activities are often shared with my spouse and kids, ensuring that they remain a focus.

  5. I love how you conceptualize your thoughts. Certainly it can’t be black and white – that all overachievers would succeed in a freedom-oriented work environment and vice versa that others could not. I would imagine you would succeed handily 🙂

  6. I’m not sure I agree with the dichotomy or not: that there are people who are suited to a typical work arrangement, and those who are not. You may indeed be right, and I simply am resisting the idea of being categorized, or having a predisposition to certain situations, like a 9-5.

    I am more comfortable with the idea that we are capable of adapting to a new work set up, can build our resistance to the siren call of Breaking Bad, & can, over time, sharpen our focus to produce results as needed. But I might be a bit naive…like thinking we’re all unique snowflakes who, despite our uniqueness, can perform well in any work situation whatsoever.

    Anyway, kind of rambling thoughts there. My gut says you are right…but I don’t want you to be. 🙂

  7. Interesting idea. I do think it takes a certain kind of person to manage “work freedom” as some need to have work and accountability structured in order to get things done. I think the biggest danger for “work freedom” people is letting work take over everything- even that family time that those on a more flexible schedule think they will have more of. What can easily happen is you work all the time- all day and all night and on the weekends. There are no stop signs that remind you to stop working and spend time with your spouse or children. These stops signs are built into a 9-5 schedule. I finish work- I go home and now it’s family time; no more work now. Having “work freedom” means you need to create your own stop signs for your personal life or that “stay-at-home” mom/dad is really a work 24 hour parent/spouse with little time for what they claim is most important- personal relationships. I actually think maintaining a work/life balance is easier when you work on a traditional schedule.

Free resources and support, every Friday: