How to Cope With the Psychological Demands of Being an Entrepreneur


The “side hustle” is becoming more mainstream and popular, meaning the average person is likely to be on an entrepreneurial track without realizing it. If you sell goods on Etsy, do freelance design work, coach the women alumni from your alma mater, or write a blog about your dating adventures then you are cultivating a side hustle with the potential to be your full-time bread and butter.

If you’re living the entrepreneur life or know people who do, chances are you’ve seen the many challenges that come with this lifestyle: the sleepless nights, financial uncertainty, etc. What no one tells you about entrepreneurship is the psychological cost people also pay. There are those individuals who are fine. They don’t stress and they don’t internalize the chaos of living an uncertain professional life. For others, sanity becomes that thing we put on a layaway plan, with the hopes of paying in full, eventually. I have lived through both versions and I have the battle scars to prove it. 

Over the last five years I’ve learned some strategies that helped me cope with the emotional roller coaster of pursuing a professional life rooted in uncertainty, here are my tips.

**Full disclaimer: I am not a clinical psychologist but I am a seasoned entrepreneur who lives with chronic depression and varying degrees of anxiety (generalized and social). Such “challenges” have empowered me with amazing insight. 

All feelings have a shelf life.

“This too shall pass” is something I remind myself when things are going great just as much as when things are going not so great. Life is all about ebbs and flow and learning to respect the low moments and not feel ashamed of them has given me the courage to keep moving.

Don’t wait until you need help.

My moods are very cyclical and with that comes a certain level of predictability. I leverage that insight to create a support system so that I have help nearby when my energies shift towards a downward spiral. No one knows you better than you so identify your patterns and use them to your advantage.

Plan for everything, literally.

Prepare for “WTF moments” which are usually the perfect storm of a website going down, clients bailing and personal life turmoil all at once. I have an alarming affinity towards spreadsheets because I will plan out every single detail of a launch, sales funnel, sitemap, etc. Yes, I am a control freak and yes there is Virgo somewhere hidden in my natal chart but above all things I hate surprises, so I plan for them.

Remember your why.

Entrepreneurs who are so focused on the goal risk losing track of their why. Your goal is a destination point. Your why is the fuel that allows you to get from point A to point B. Figure out your why before others determine it for you.

There is no right or wrong way to approach entrepreneurship. There is only the way that works for you. There’s an amazing sense of empowerment and magic with entrepreneurship, even if it’s just a side hustle. Just make sure to prepare yourself for the journey because it’s more than just reaching a goal, it’s realizing your authentic self and purpose, while nurturing yourself along the way.

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