It’s Not All Sunshine: How to work through the “gray days”

Much of entrepreneurship has been glamorized thanks to the rise of social media and movements like #bossbabe and the like. We see more people than ever before sharing the highlight reel of their entrepreneurial journey. Most often, what we see is carefully crafted content designed to portray success, wealth, freedom, comfort, and luxury. And while that may certainly be one “sunny” aspect of entrepreneurship, please hear me when I say it is merely a tiny fraction of the larger picture. What does the larger image of an entrepreneurial life look like? It’s a colorful and wonderfully chaotic mosaic that has both dark and light elements, times of success and times of struggle, and happy and heavy emotions.

Recently, for no particularly large reason, but rather a hundred little reasons, I felt storm clouds rolling into my usually serene and content picture of entrepreneurship. I wasn’t shocked; they roll through from time to time. Sometimes they come with a warning – maybe it’s because of some disheartening news or a particularly stressful week where there is more demanded of me than usual. Other times, the clouds gather for reasons I can’t pinpoint. In fact, there may be a lot of great things taking place, but my mood simply shifts to a darker space. What I’ve come to learn is that along the road of entrepreneurship, the weather is not always sunny and it’s never predictable. Instead, we are best to walk this road with an understanding that we’ll be faced with a wide variety of experiences. Some will feel like sunshine and a cool breeze, others will bring rain and whirling winds.

It’s not possible to carry every accessory to keep us comfortable along this journey. Rather, it’s much wiser and more sustainable to learn to keep up the pace even when the “weather” is less than ideal. So in this instance, I simply needed to recognize the clouds rolling in and work through the “gray days” knowing that soon enough the sun would return. It sounds simple, but I know that when you’re in the eye of the storm it can be overwhelming to see your next foot forward. Here’s my tried and true advice for surviving inclement weather on the entrepreneurial road.

Name and Claim What You’re Feeling

One of the worst feelings is the uncertainty of what you’re actually feeling. To alleviate this uncertainty, the best thing you can do is to “name and claim” your emotions. Give yourself some space to process what you’re really feeling. We get so busy in life that often our minds can’t fully process our emotions and correctly correlate them to the experience that’s causing them. This may lead us to believe that we’re feeling a certain way due to something that is not at all the cause. Pause, breathe, and process the thoughts and emotions swirling in your head. Are you anxious, stressed, hurt, feeling unappreciated, overwhelmed, or something else? Now really try to link the root cause of these feelings to the moment that caused them. Did you receive unfavorable news? Is there a strain on a relationship? Is there a deadline or a big decision looming? By naming and claiming your emotions, and properly compartmentalizing them with their cause, you can begin to create breaks of blue skies among the dark clouds hanging overhead.

Reset Your Reality

One bad interaction, negative conversation, or stressful situation does not need to paint your whole day gray. I’ve found a lot of value in resetting my reality by focusing on what’s going well. Start by listing everything you can that’s working in your favor – both big and small. You’ll always be surprised by everything you take for granted. And in listing all of these little “wins” you’ll see that they far outweigh whatever reasons you feel you have to be gloomy. All is not wrong in the world. In fact, a whole lot is going right. This doesn’t mean you should dismiss your sad, mad, or anxious emotions, but it does help to bring you back to the reality that what you’re feeling is only a reflection of a small piece of the larger image. And you can take heart in knowing that once you’ve worked through these emotions, the clouds will clear.

Be Honest About What You Need in this Moment

Once you’ve gotten in touch with what you’re feeling and why you’re feeling this way, what do you really need in this moment? Be kind with yourself and give lots of grace. For me, I often need solitude, time spent in nature, and more sleep. I need to do something “nice” for myself rather than cracking the whip harder. So often we are own hardest boss and toughest critic. This is an opportunity to be gentle and understand that right now you’re a bit delicate. It may even be appropriate to share this with people around you – a spouse or coworker who may take notice that you’re not quite on your A game. Simply saying, “Hey, I’m having a “gray day” today. I’m not quite feeling myself, so I might be taking some extra time to myself. I’ll let you know if there is anything you can do to help.” This helps bring them into the fold so they can also extend you the grace and space you need to get to the other side of the clouds.

Play It Forward

And finally, we can further reset our reality by playing forward our worst-case scenarios. There have been weeks where I felt like the sky was falling because of a bunch of projects, events, and deadlines coming to a head at once. I felt like there weren’t enough hours in the day to meet everyone’s demands and to also protect time for myself. What helps me is to play it forward. Usually, it’s only a hump of a day or two I need to get through and then there are clear skies ahead. If I’m nervous or frustrated about something, I can play forward what will happen if my worst fears are realized. I’ve yet to encounter a worst-case work scenario that’s life-threatening or that truly risks ruining my entire business. More often it’s a mild inconvenience or disappointment. I can live with that! The most important thing to remember is to remain calm and confident in your identity. Whatever storms blow your way will pass – they have to eventually – and so long as you’re deeply rooted in your passion and purpose, you’ll emerge on the other side with your values in tact.

Whether as part of business ownership and entrepreneurship, or simply part of life, how have you had to face your “gray days” and what have you found to be most helpful? Join the conversation in the comments!

4 thoughts on “It’s Not All Sunshine: How to work through the “gray days”

  1. Welcome insights. Re. “One bad interaction, negative conversation, or stressful situation does not need to paint your whole day gray”: one productivity book I read (Ed Bliss, Getting Things Done) suggested at the end of each working day asking yourself, “What’s the biggest thing that’s happened today?” Often I have days where, say, half a dozen things don’t go well and I think, “This has been a bad day” – but when I take Bliss’s advice I find the biggest thing that’s happened has actually been positive – I met a deadline, received a new commission, or whatever.

    1. I really appreciate the comment, and this is great advice. If we end our day by reflecting on the “biggest” thing, it should really help to keep our perspective on what matters most. The wins, the things that could have gone wrong, but went right, the moments spent in relationship with those who mean the most to us. In doing so, those “papercut” wounds will seem less important in comparison.

    1. Absolutely! It would make sense to lean into that fact, yet human nature can cause us to fight it with everything we’ve got. Maybe someday I’ll embrace my own words of wisdom enough that they’ll “stick” but for now I write and repeat them often 🙂

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