When Entrepreneurship Stops Feeling Like Winning 5 tips to Anchor You During Your Toughest Days

What if I can’t fix this?

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Just a few weeks ago, I found myself shame-spiraling, heart in my throat, fear overriding my typical ability to think straight.

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My 7.5-year-old company Shoott has been (and still is as of this writing) facing unprecedented digital marketing challenges, resulting in a 35% year-over-year drop in demand for 1Q26. As a business with incredibly tight margins, this kind of performance raises all the existential questions: 

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What if we can’t figure this out? 

What if we run out of money?

What if we lose our business? 

We support 15 full time employees and ~1000 freelance photographers - what will happen to them?

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Running a company means you don’t get the luxury of spiraling for long. People are relying on you. The business still needs decisions.

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In the journey of entrepreneurship, there are so many wins: each new client, hitting new revenue milestones, awards and press mentions. Those moments are amazing, but they’re also just the LinkedIn highlight reel.

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Because if you’re an entrepreneur long enough, there will be some hard phases or as my therapist calls it: “near-death experiences.”

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I have yet to figure out if I’m having the near-death experience or whether I’m actually dying (it feels like I’m dying); so while I’m still in the middle of this chapter, I feel compelled to share my 5 “survival kit” mental health habits that enable me to still show up each day despite the fear and the tears in the hopes that it will help a fellow entrepreneur in the future:

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1. Practice what keeps you regulated

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When things are truly stressful, the idea of taking a mental health break isn’t always realistic.

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Your company still needs leadership, so your goal must be regulation because you and your company need your nervous system functional enough so your brain can do what it does best.

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So, I make sure to commit to these 3 areas regularly no matter how I’m feeling:

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Physical Habits

When the day is chaos, find a way to consistently get out of your head. Stress hormones need somewhere to go and the best practices that have helped me are exercise (yoga, HIIT, pilates, walking) and breathing and meditation exercises to calm the noise - whatever it is, give your anxiety a break and let your body support you.

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Food

Under pressure, founders can either undereat or stress eat. Try to commit to eating real food (whole foods, fruits, vegetables, etc) and meal prep if that helps. But giving your body proper nutrition is one less thing to stress over when everything feels like it’s falling apart. 

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Sleep

Aim for at least 6-7 hours to give your brain enough time to flush out all the stress hormones so you have all the mental energy the next day to tackle what’s ahead. 

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These things sound basic but when you're under intense stress, they’re easily neglected. Taking care of your own body and brain can be the difference between spiraling and thinking clearly, so do not compromise on these!

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2. Know your people

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In hard seasons, your people matter more than ever. They’re the ones who cheer for you and keep you straight:

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Close friends and family

Other founders who “get it”

Your therapist if you have one (highly recommend you find a good one ahead of time!)

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When things get scary, you need people who can remind you of what you are capable of and that you are more than whether your business succeeds or fails.

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Sometimes you just need someone to listen while you crash out for a minute and then get you back to a place where you can lock in.

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Community doesn’t solve the business problem, but it helps you survive the emotional weight of it so you can be your best self for your business.

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3. Know who to avoid

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This one is underrated - but when you’re in the middle of the storm, be careful who you take advice from.

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A lot of people structure their lives around avoiding risk, pain, and failure, which is totally reasonable for the average person, but is unhelpful when you’re on the journey of entrepreneurship.

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It’s the voices that say things like:

Maybe you’re not cut out for this…

Yeah I never thought your business would go anywhere…

It’s so much responsibility - are you sure you won’t disappoint everyone?

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“Advice” from someone who doesn’t understand the inherent level of risk to entrepreneurship can make you feel worse, not better. And the last thing you need is someone unintentionally amplifying your anxiety instead of helping you think clearly.

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So just be careful which “voices of reason” you let in - if someone tends to trigger you when you’re already unregulated, it’s okay to step back and talk to them later when things stabilize.

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4. Process Your Emotions

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You cannot just repress fear and expect it to disappear because it will always end up biting you via burnout, irritability, or decision paralysis - just to name a few.

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You have to process things.

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For some people that’s journaling.

For others it’s talking it out.

For others it’s a long run or a good cry.

Whatever it is, let the emotion move through you.

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Entrepreneurs are often expected to be endlessly strong, but strength isn’t pretending you’re fine.

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It’s you letting yourself look fear in the face and continuing anyway. The vulnerability and bravery is excruciating in the moment but this is where you build capacity and that founder “grit.”

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5. Be kind and patient with yourself

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Running a company means carrying an extraordinary amount of responsibility.

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Jobs.

Revenue.

Customers.

Your team.

Your own financial future.

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For high-achievers, the instinct is often to manage that responsibility by being brutally hard on yourself. But that strategy has limits.

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When the pressure builds, the weight of everything can start to feel crushing. It’s easy for your brain to start catastrophizing all the worst case scenarios all at once, which is simply too much for any human nervous system to hold.

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So be kind and patient with yourself.

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You’ve already survived every hard day you’ve ever had. You’ll survive this one too, even if you don’t yet know how.

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And the reality is, none of us actually knows how things will turn out. The future you’re fearing might unfold very differently than you imagine. It might even lead somewhere unexpectedly good. So be gentle with yourself as you figure things out.

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So many of us chose entrepreneurship because there’s excitement in not knowing what the next day will bring. But the flip side of that freedom is that some days are genuinely scary.

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Over time, part of becoming a founder is expanding your capacity to sit with that uncertainty.

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If you’re in the middle of one of those storms, know you’re not alone. Nearly every entrepreneur who has built something meaningful has been there.

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Not everything is solvable.

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But most things are survivable.

And tomorrow is another chance to try again.

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