How I Manage the Dark Side of Entrepreneurship


Alright my friends, today I want to get REAL real. I'm writing about some of the cons of entrepreneurship that not many are willing to open up about. Sure, there are a lot of pros and 50% of the time I do feel like I’m “living the dream,” but the other fiddy? Yeaaaaah, that other 50% can be ROUGH. There are a lot of struggles entrepreneurs face daily that we keep quiet about. Mostly because we’re exhausted but also because we’re trying to keep up appearances that we have our shit together. 

Here’s what I have under my belt so far. 

+ Over 6 years of experience consulting entrepreneurs and business owners 

+ Raised over 2 million in revenue for a local media/technology company 

+ Created a profitable online jewelry collection and outdoor yoga company

+ 1 failed business venture

+ Co-created and launched a successful start-up, and made an exit from said company 

+ Created and launched a successful Marketing/Consulting firm [this one]

I became my very own business owner last year. When talking about what I do with most people, I get reactions like I’m living some financially abundant lifestyle with lots of leaf-foamed lattes. In reality, my french press is less luxurious but saves me over $50 a month in coffee shop expenditures. I’m constantly projecting revenue and wondering when it’ll all come crashing down. I question my sanity and curse in my office a lot. I try to make time for an epsom salt bath everyday because my muscle tension is slowly turning me into Quasimodo. Sexy.


While most people navigate the waters of the good ol’ 9-5, socially engaged and stimulated, I spend a considerable amount of time alone. I’m the kind of person who loves short periods of alone time, but prefers to be surrounded by others. I’m not a loner, never have been. Unfortunately, I work out of a home office and building a business drains ALL of my time. There’s no such thing as “free time” anymore. Working so much has adversely effected my personal relationships. I’m not to able to spend as much time with my best friends and because I work from home, the lines between real life and work life are so blurred that I never really know when to turn off. 

Then there’s the problem of having to answer small talk questions like, “What do you do?” For entrepreneurs, explaining what you do for a living can be exhausting. The question is often avoided because, when answered, people have a tendency to make unfair comparisons about their own lives. I NEVER want to make someone else feel small, and quite honestly that tends to happen when people ask about my work. We have a tendency to unfairly compare ourselves to others and feel inadequate without understanding the full story. It’s uncomfortable for me. 

It’s easy to talk about what I do if I’m networking or in a meeting. It’s another story when friends or acquaintances ask in social settings. I find myself not wanting to talk about it, dulling my accomplishments, and being vague in general. My standard “elevator pitch,” means nothing to the squad. To avoid coming across as an arrogant prick, or mindlessly chattering a mouthful of jargon, I try to quickly explain and then change the subject. This inadvertently creates feelings of detachment from most working adults in the standard 9-5 realm, and has caused me to gravitate towards only spending time with other entrepreneurs who “understand.” 

Tip: I overcome feelings of loneliness by confiding 1-2 friends who I know I can vent to or even celebrate successes with. When I’m feeling overwhelmed or frustrated, I rely on a few older and wiser mentors to talk me off the ledge. And lastly, when I feel lonely I’ll step away from work and join the public for a while. Sometimes just being in a coffee shop or restaurant full of people is enough to make me feel like I’m a part of society.

Control Issues. 

My issues with control likely stem from being the middle child raised in a strict Marine Corps family. I didn’t have control over DIDDLY SQUAT I’LL TELL YA. There was an endless sea scroll of rules that made me adversarial to any form of authority. Sorry mom/dad… you had the best intentions, but being strict just inspires some of us to retaliate. I was never allowed to be in trouble so I CRAVED IT. But don't be mad Ma, it’s working out in my favor now.

It's not just me. A common denominator I’ve seen amongst entrepreneurs is the need to have absolute control over their environment and business. Most of us can say that we’ve been described as “difficult,” either from parents, teachers, or managers. I remember one high school teacher in particular constantly chastised me for my "apathy." Never really had a passion for Geometry and only did well in the subjects I enjoyed. I digress. A couple of managers throughout the last 10 years have scolded me for an inability to “take criticisms.” I will retort by saying that I can learn from most criticisms, I just can't always hide the reactions on my face when they're given to me. LOL. 

And again, I’m not alone. Every entrepreneur I have ever met has agreed that they have been described as a “difficult employee” and often times felt like a misfit in typical work environments. We feel suffocated by imposing structures, processes, and guidelines - as if an authoritarian is holding us hostage. There is one exception to this… we don’t feel stifled by the guidelines that WE create. Now that would just be silly. ;) 

In terms of letting go of control, I have personally found that removing tasks and projects from my plate is a terrifying thought. I am unable to trust and let go because of the fear that it won’t get completed, but mostly because it won’t get done “right.” This can stifle growth and limit creativity - and it is something that I am actively working on. I realize I am cursed with a high-strung, Type A personality, and if I could find a tiny bit of balance perhaps life would be a little bit easier. 

Tip: Something that helps me to let go of control is asking myself, “what am I worried will happen if I don’t have control over this project/event/situation?” If I’m in a position where I need to be the “subordinate”, I choke down my vomit, bite my tongue until it bleeds and ask myself, “what can I learn from this experience?" That way, it doesn’t feel like an authority figure domineering my every move - and more like a lesson that will help me become more successful in the future [which, honestly, is often the case].

Mood swings. 

Being overworked, neglecting personal relationships and health, and the fear of failure all contribute to mood swings that entrepreneurs can frequently feel. Spinning so many things in the air, there is a gnawing feeling in our stomachs that at any point it can all come crashing down. Pressure to reach an ever-raising bar, to maintain appearances, and the general pressure of running a business in its early years causes bouts of depression and anxiety like you wouldn’t believe. Every 1 in 4 people suffer from these conditions, so it’s no shock that even the most successful entrepreneurs and business owners can feel this way too. 

I’m genetically predisposed to anxiety and depression because, family. Ever since I was a child I’ve dealt with both. And this is probably the least discussed challenge of running a business because these conditions are so taboo that no one talks about it. I'm not ashamed of my anxiety and depression and in fact, I'm proud of my ability to manage both via natural means (although there is NOTHING wrong with using medication).

 During the first few months of running my business I started to feel isolated. I went from a  fast-paced corporate lifestyle where I was constantly socialized, to spending by my lonesome. I didn't feel successful because there was no one to applaud my successes. The stark contrast in my daily routine took a while to adjust to, and I found myself feeling desperately hopeless. Some mornings I would wake up and feel completely useless. I could hardly see the difference between myself and a homeless man peeing on the street. A slight over exaggeration, but I felt like a BUM you guys! I'd have to fight through my day working with this thick & evil brain fog. To compliment my feelings of hopelessness, the uncertainty of where my life was headed caused ripples of anxiety. So I felt like a homeless man AND a nervous hampster. Cute. Truth be told, spending so much time alone made the voice in my head so much louder...and the voice in mine is not always pleasant. 

Tip: First and foremost, be patient with yourself. Be nice to yourself for god sakes. Take frequent breaks throughout the day to clear your mind and get away from work. Spend time outdoors and, sunshine permitting, soak up some rays to make sure you are getting enough vitamin D. Exercise every day - no excuses. Rely on 1-2 trusted friends or family members who you feel comfortable being honest with if you are feeling depressed or anxious. Mediation. Cashews. Lots of water. 

Neglect of Physical Health.

I was crunchy granola before it was cool. In 2009 I was teaching upper-middle class white people what green smoothies were. SPINACH IN A SMOOTHIE?!?! WAIT WHAT'S KALE?! You should have seen the looks I got. I was diagnosed celiac before gluten-free was a fad. I won’t go on - you get the point. 

 It goes without saying but I'll say it anyway- I try my hardest to eat as naturally as possible and limit my exposure to harmful toxins and chemicals. But alas...I be runnin' a bidniss. It’s amazing how a decade of self-discipline deteriorates the minute you’re forming an S-corp. I find myself shorting my body of nutrients and eating for convenience vs taking the time to feed myself properly. I’ve never EVER been one to “forget to eat,” but sometimes there is literally NO TIME to stop and get something. This effects my already delicate mental state. 

Then there’s the stress that compounds from never knowing when the next contract is going to land, to working 18 hour days for months straight. I have such extreme muscle tension in my neck and shoulders that I can’t even FEEL deep tissue massages. My acupuncturist tells me to relax my head while she holds it in her hands, and while I swear I’m relaxed, she tells me otherwise. To add insult to injury, stress has gifted me with a relentless 8-week bout of bronchitis and 3 zits with their own pulses have harbored on my face. I haven't had bronchitis in 6 years and my skin has been clear since I was 20. COMPLETE AND UTTER BULL SHIZZ.

Many entrepreneurs I have met end up abusing substances and alcohol to manage the stress of their daily lives. I am no stranger to this. I rely on a full french press to power me through mornings. I used to only drink one cup. Often times unwinding at the end of the day means sharing wine with friends. Sales people, entrepreneurs, and business owners are no stranger to the sauce, either - because many times meetings are held at happy hours or schmoozy dinners. Being "on" constantly leads to the desire to "turn off," and we often times don't know how to do that in a way that's natural or healthy. It's a slippery, dippery, slope I'll tell ya.

Tip: When I recognize that I’m neglecting my health I try to halt immediately. I monitor my water intake to make sure I am drinking 8 glasses per day. I take the time to make myself something “green,” i.e.: full of plant based nutrients. I’ve never had an issue with sleep (thank god), but I would advise entrepreneurs who struggle with this to buy some melatonin and a good book. Limit exposure to light an hour before bed. Keep your phone across the room.

On a positive note, I absolutely love being an entrepreneur and running my own business. I have grown as an individual and professional in ways that I never would have if I had stayed where I was. The power of being able to manage my own day and decide what I will and will not invest my time and energy in is liberating. My #1 passion and hobby in life is travel, and I am able to go anywhere at a moments notice. I wouldn't trade much to give up the lifestyle I've created for myself and I am very proud of it. However, it doesn't come easily and it doesn't come without a price. I hope that by being open and sharing such personal information with you all, you can relate and not feel alone. I know that there are so many of you out there who feel this way and don't feel comfortable opening up about it. There is nothin to be ashamed of and in our struggles we learn, develop and grow. 

I'm curious to hear if you experience the same challenges I've mentioned above. Also curious to hear challenges that I haven't mentioned. Let's hear it!! :)