How to Minimize Feelings of Guilt During Time-Off Work

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For many of us, transitioning from work mode to non-work mode isn’t a simple flick of the switch. Our work carries over into our personal lives and vice versa. When we’re not working, being productive, or engaging in activities to fuel our self-growth, guilt tends to seep in. We feel guilty  because we think that we should be making better use of our time; that we’re not making as much traction as we should in our business. We still have so many items on our to-do list—a list, by the way, that never stops compiling.

I dove head first into the life of self-employment in 2016 when I quit my full-time job at a digital marketing agency. The rationale behind the difficult decision to leave the security of traditional employment was to create my own schedule—to have more time and freedom in my day to work on meaningful work of my choosing. However, what I was not anticipating was a dark, looming shadow that stalked me: the guilt I felt when not working. While this was a familiar emotion I felt it while working full-time, becoming my own boss—being fully accountable for my own shit—amplified this emotion tenfold.  

As time went on, I have gotten better at allowing myself to fully enjoy time where I’m ‘switched off’, but it’s still no easy task. Even though I accomplish much more in less time than I did while working in office environment, I still feel like I should be putting in more hours—experiencing ongoing thoughts that I’m underdelivering.

As I wrote about in my post Multiple Income Streams + Low Overhead = More Flexibility and Enjoyment in Life, I’ve structured my life so that I can have more freedom in my day to pursue more meaningful activities. Not more time to waste away, but rather, more time to feed my soul—to do things that are important to my own self-growth. Reading and conducting deep dives in various disciplines, running and lifting weights, spending time with family and friends, and writing are all important activities that I prioritize in my day. While none of these activities earn me a steady and predictable income, the time spent on said activities brings me the most joy and fulfillment in my life. In the past, I didn’t allow myself much time for any of these activities because they didn’t directly pay the bills. When I did take some time out my day to pursue activities outside of my freelance gig, I would feel debilitating guilt.

It’s taken a combination of awareness, time, and reflection—making a cognizant effort to feed my mind with justifications to engage in and enjoy these activities, guilt-free (more or less).

The guilt still lies dormant in the shadows and continues to creep up from time-to-time. I know I’m not the only self-employed person that experiences this. In fact, I can almost guarantee that almost everyone who works for themselves has felt this emotion during time-off.

In this article, I’ve recruited the help of an expert on this exact topic who also happens to be my cousin. Sara Ross is a Keynote Speaker and founder and Chief Vitality Officer at BrainAMPED: a leadership research and coaching firm aimed at redefining how people succeed and thrive through stress in work and in life. Sara is also in the process of writing a book titled Dear Work: Something has to change where she shows people how to reignite their Work Vitality Quotient with brain-based strategies focused on energy management, emotional intelligence, and resilience.

Sara has graciously offered to contribute her research on the topic of guilt; something she’s explored in-depth. While this article is more tailored to those who are self-employed, I think everyone who struggles with this emotion during periods of rest can draw some valuable insights. In this article, we’ll first dive in to why we feel guilt in the first place then deduce some strategies on how to minimize guilt and reframe leisure activities (for those that still struggle). 

Why Do We Feel Guilty When We’re Not Working?

To make a change in our lives, the first step is always awareness—that is, trying to understand and dissect why we feel how we feel. What are the reasons behind the guilt? Where are they coming from? When I asked Sara this question, she explained that there’s no single answer—it’s a complex question filled with nuance—dependent on each individuals situation. However, when conducting interviews for her upcoming book Dear Work, Sara did spot some trends.

The Bottomless To-Do List

“We see rest as a reward,” writes Sara. Therefore, if we don’t finish everything we feel we need to do in a day, we don’t feel like we deserve  breaks and downtime. The issue is that our lists are endless or “bottomless”—there is always more we could be doing. So therefore, rest and leisure, or doing things that aren’t classified as work-related, never really feel earned. “Due to this often-unconscious belief, we feel guilty if we engage in leisure when there are still items to be crossed off our to-do lists,” writes Sara.

So rather than opting to take a break that “would replenish our energy and capacity to get things done”, we sit and fester in self-deprecating thoughts. “We continue to berate ourselves for the lack of traction we think we should be making,” writes Sara. We then get stuck in a spiral or what she calls “a negative feedback loop” where we feel guilt about not working then guilt that we should be taking breaks. Rinse, repeat.

Workaholism: a Real Addiction 

Workaholism, akin to other addictions that have a pernicious effect on our mental health, can easily overtake and dominate our lives. “We are obsessed with being productive and addicted to being busy,” writes Sara. “Even our ‘down time’ has turned into ‘do time’.” Sara calls this state, toxic productivity which in her words is “grounded in the belief that if we aren’t being productive then we are wasting time.” This inevitably leads to feelings of guilt.” Hustle culture and competitiveness with others can easily make this a rat race with no real end—leaving all participants burnt out, unfulfilled, and even depressed.

We’re Uncomfortable with Uncomfortable Feelings

As aforementioned, the first step in making any sort of change is awareness and that means that we sometimes need to both sit with and tune in to said feelings. “Emotions are not a problem; they are healthy and natural—an important source of information,” writes Sara. “The problem comes from how we respond to those emotions.” When we feel the onset of guilt creep in, Sara suggests that instead of “slowing down” and investigating the emotion by looking inward, we try to override it by working more. Just as an alcoholic takes a drink to numb their feelings, working more has a similar effect. 

Instead of trying to numb the guilt, attempt to understand the feeling first. Once understood, we can then find mechanisms for dealing with the guilt. Sara suggests journaling the responses to these questions:

Have you taken on too much? 

Are your priorities out of whack?

Have you tied your self-worth to your work success? Or in other words, is your identity fully wrapped in what you do for work?

These are indeed uncomfortable questions, but at the same time, thought-provoking ones. “Evaluating [guilt] with openness and vulnerability will move you closer to the best version of you versus the guilt driven version of you,” writes Sara.

How to Manage and Minimize Guilt During Time-Off

Not going to lie—minimizing feelings of guilt is still a big work in progress for me. While I have gotten better over the years, it’s still a challenge to feel fully relaxed when I take breaks, days off, and vacations—assuring myself that my businesses aren’t going to crash and burn. Over the years I’ve been able to devise some strategies that move the guilt from the forefront to the back and no, the solution is not working more. Sara and I have put together a list of how to reduce guilt—allotting ourselves more time to pursue other “non-work” activities guilt-free.

Plan Ahead

The feelings of guilt can lead to what Sara coined as the “Might-As-Well-Work” mindset; the belief that if you don’t have something better to do (or are too tired to actually think of anything else), your default mode might be to do more work. Which in turn, alleviates the feelings of guilt and boredom. It can become habitual so in order to combat this, Sara recommends planning ahead—creating a list of other non-work related activities to do if the familiar feelings of guilt or boredom begin to seep in. 

Do this exercise with family and friends. Ask coworkers for ideas, Google cool things to do. Get as diverse of a list as possible; some more active (like going for a walk) and others more relaxing (like going for a massage). Include items where you can give back and contribute to others in your community and some for your own self-care.

By creating a blueprint and planning ahead, you’ll be better equipped to overcome the onset of guilt. Rather than flailing and defaulting back to work mode, you have a list of items ready to go. Do one of those activities instead and see what happens!

Give Yourself Permission

When you do plan a break for yourself, you need to give yourself full permission to take it guilt-free. While this may seem obvious, it’s quite common for us to default back into the thought patterns surrounding what we “should” be doing which Sara says “is one of the most counter-productive things we can do.” 

Give yourself permission to stop working. But more importantly, give yourself permission to stop feeling guilty about not working. If that feels too hard, put a time parameter around it; for the next two hours, I give myself permission to stop thinking about work and do whatever I want.

This goes hand-in-hand with planning ahead. By carving out designated times in your day for rest, you’ll be less likely to feel guilt and more likely to be present and enjoy the allotted time-off.

Listen for Old Stories

A great metaphor for the stories our minds play on repeat are what Jon Acuff calls “soundtracks.” If you really tune in and listen to the songs (our thoughts), many of them are trash music produced in your parent’s basement that are on a continuous, never ending loop.

“We have old narratives that run through our mind pulling us back to [our work],” writes Sara. She explains that the biggest culprits for triggering guilt are thoughts that start with “I should” or “If-then.” For example, “If I can just get this thing done, then I can really enjoy myself later.”

Tuning into our patterns of thought can help us become aware of the stories we tell ourselves that lead to guilt. “Start by simply paying attention to your thoughts with a mindset of curiosity and self compassion,” writes Sara. Realizing that these stories are mind-made fiction, we can change the narrative—a powerful antidote to guilt.

Set Your Work Day

When working, it’s essential to set some boundaries surrounding your work hours. You can either make it hour-focused or task-based. I prefer the task-based model where I write out my to-dos and once those are done, I am done working for the day. Sara, on the other hand, sets her work hours; something she said  “has been the hardest yet most impactful thing I did after starting my business.” To hold herself accountable, Sara added her work hours to her signature; which she graciously provided here (for you to steal):

My working day may not be your working day. Please do not reply to this email outside of your normal working hours. I check email weekdays between 9am-7pm (EST), if you need something urgently outside of these times, please call (xxx-xxxx). Thank you!

If you’re traditionally employed, this may be outside of your control given ‘work hours’ are set by your employer, but being self-employed can oftentimes feel like the wild west. Setting your work day is entirely individualized, but one important rule still holds true: once you’re outside of your hours or have finished the tasks you have set for yourself, it’s time to turn off entirely. 


In a similar vein, I think when you’re self-employed, it’s essential to create some structure and regularity in your day. Otherwise, it feels akin to free floating in space—drifting from one random task to another then at the end of the day, wondering what you even accomplished. This can once again lead to guilt and feelings of not doing enough. Time blocking has helped me (when I actually follow it), but I also allow some wiggle room to move tasks to other days if I’m tired or foggy-minded. I’ve made it into a nightly ritual to review the tasks I’ve accomplished for the day and write out my to-do list for the following day. 

I follow Brian Tracy’s advice to “eat that frog” and prioritize my most important and typically hardest work in the early hours, but not before I have some time to myself. If I wake up and beeline it to my desk then proceed to start working immediately, I always feel anxious and can’t produce the quality of work that I’ve come to expect of myself over the years. I need to wake up slowly, meditate, read, sip on my coffee and wake my brain up. Here’s how I currently structure my morning activities: 

Meditate + read – 1-1.5 hours
Write – 1-2 hours
Workout (run + lift weights) – 1.5 -2 hours
Shower + eat (45 mins – 1 hour)
Freelance work – 2-3 hours
Reading or listen to an audiobook and going for a walk – 1 hour

I move things around if I have meetings, but by structuring my day, I’m able to squeeze in a combination of meaningful work with paid work. I mix working on my self improvement with earning income. At the end of the day, when I’ve finished what I’ve defined as ‘work’, I can allow myself time to do non-self improvement activities; hangout with friends, go for a walk, watch some trash TV, or take a nap and play on my phone. 

Deep Work

The days where I feel most anxious and guilt creeps to the forefront is when I’m switching tasks like a mad woman—jumping around from task to task, bouncing from email, to slack, to meetings, to checking social media, to ordering a new pillow off Amazon. This phenomena is what Cal Newport calls in his new book A World Without Email, “hyperactive hivemind.” Distractions and notifications pulling us from one task to another leaves us feeling drained and exhausted with very little to show for it. The value we bring to the table is not a matter about how many tasks we can check off our to-do list, but rather, “our ability to focus.” Newport suggests a more linear approach to workflowfocusing on a single task at a time (distraction-free), before moving on to the next. 

Turning off distractions and being fully immersed in a single task at a time increases the likelihood of getting into a flow state—where time seemingly flies by and you feel fully immersed in the task at hand. Flow has a cathartic and meditative effect. This state is only possible, however, if notifications and distractions are turned off. I realize that not everyone has the benefit of working completely distraction-free (myself included), but even for small periods of time we can reap the benefits. For example, I try most nights to turn my phone on airplane mode at 9:30pm and not turn it back on until the following morning once I’ve finished my deep and most important work. Right now, that means working on the edits to my book and writing articles. Once that’s done, I can check my email, notifications on my phone, reply to text messages etc. 

I’d love to tell you that I have the self-discipline to work like this every day, but the truth is that I am human and also am kind of addicted to the dopamine hits of incoming messages and social media notifications. On the days where I’m really able to take a hold of my distractions, I significantly reduce the guilt and stress of not working after I’ve finished work. At the end of the day, I feel like I made a real contribution and am not questioning where my day went.

Focus on Your Bigger Contribution

Aside from just doing work for the sake of earning income, I’ve changed the way I define work. For me, it’s no longer just a monetary exchange of money for time, but rather, how I can make a meaningful contribution to someone else’s life and to society at large.

The point is that the work that feels the most meaningful (to me at least) is when I feel like I’ve made a contribution. This has not only minimized the guilt I’m feeling when not working, but has also given me the intrinsic motivation to actually sit down and do the work; to show up day in and day out for my clients and creative projects. 

I pose this question to you: what tasks can you work on where you feel like you can make the most meaningful contribution to others? Figuring this out may not be easy, but I can personally attest that once I defined these tasks for myself (ie. my book, writing, consulting clients on how we can build their business through advertising) and chipping away at these tasks each day, I feel less guilt from unplugging and taking time off. I feel it almost on a spiritual level. When I’m just checking off things off my to-do list and bouncing around, I never feel fully satisfied at the end of the day. It’s at those times when anxiety, stress, and guilt are more likely to emerge.

Reframing Leisure Activities 

The last point is important. While we shouldn’t ever have to justify leisure time, by using the technique of reframing, we can take more guilt-free time off to engage in other activities as well.

I’ve gotten creative over the years in allotting time out of my workday to read, write, and train. I use the following frames: Reading and feeding the mind with quality inputs feeds my creativity and helps me relax and focus. Writing makes me a better communicator and helps solidify my knowledge of something new I’ve learned. Training gives me the attentional space I need to work through problems and better harness my creativity—in my paid work and non-paid work. Rather than just enjoy the activities, I’ve had to create mental justifications to reframe said activities as work. 

If you’re able to do leisure and just enjoy it guilt-free, then great (I doubt you’d be reading this article then). But for the rest of us, an exercise in reframining leisure can really help in minimizing guilt. This especially holds true for the activities that have a direct correlation with improved mental health and self growth: meditation, yoga, playing sports, reading, journaling, deep conversations with friends and family, and sleep. Watching some reality TV, going out for drinks with friends, or ordering pizza and watching sports for an afternoon is completely fine too. We should be able to turn off and do activities that aren’t directly correlated with growth, but that we just genuinely enjoy. The time off will help energize us for our upcoming workweek and recharge our batteries. Sara suggests that instead of thinking of these activities as “not working,” which sets the stage for guilt to move from and centre, “reframe it as re-engaging in things that nourish and replenish you.” 

Final Thoughts

The life of the self-employed is a rewarding, but challenging one. While working for yourself offers autonomy and freedom, it comes with an important added responsibility: setting your own boundaries when it comes to time-off.

If we don’t plan ahead and give ourselves permission to take breaks guilt-free, the work life lines become blurred and other parts of our life begin to suffer. Our priorities get out of whack and we lose sight of what’s really important to us. We forget that the reason we wanted to become self-employed in the first place was to enjoy more freedom in our day and have more time to engage in meaningful work and activities. 

Understanding why we feel guilt is an important first step, then using strategies such as setting task-based on hour-based work days, limiting distractions, time blocking, engaging in deep work, and focusing on tasks where you feel you’re making a meaningful contribution, can help minimize guilt and with time, possibly eliminating it altogether. 

If you’re like me and still struggle with minimizing the guilt (especially when taking time to engage in other non-work activities during traditional work hours), try reframing your leisure activities—providing justification on how they can make you a more productive individual and even labelling said activities as work.

Guilt, like many other emotions, isn’t necessarily a bad thing—it can help motivate us to do and be better. Guilt can present an opportunity to look inward—to approach the emotion from a place of curiosity; an opportunity for self betterment. But just like patience, and many other virtues, guilt needs to be managed. I hope you found these tips helpful and I wanted to end with a huge thank you to my amazing cousin Sara for her incredible contribution to this post. To connect with Sara, you can visit her website

1 Comment

  1. Wow, such a comprehensive and well thought-out post. I myself have learned that the quicker I eat my frog, the better I feel throughout the day, and that allows me to rest without guilt. Thanks for this post!

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