Confessions of an Entrepreneur - The Emotional Grind


Being an entrepreneur, though extremely rewarding, is not for everyone. It is emotionally taxing and consistently challenging. Having been an entrepreneur since I was in high school I can tell you, starting earlier in your career definitely helps a lot. Your world is less bombarded with the usual priorities and social expectations of fulfilling some unspoken checklist of life milestones by a certain “proper” time.  Once you hit your 30s, the world seems to try at every opportunity to test your resilience.

For me, these are the top 3 issues that I deal with daily as an entrepreneur and what I have learned to combat them.

  1. Social Pressure
  2. Self-Doubt
  3. Unpredictability



Relationships Status

As a female, social pressure is for me the number one test of my strength as an entrepreneur. Especially if you come from a culture with a traditionally patriarchal mindset, expect to be bombarded with concerns for your social well-being, specifically your relationship status ALL THE TIME.

At every holiday, birthday, family gathering, and really anytime you are with a group of people who care about you, if you are single… you will be reminded that your eggs are going to shrivel up and die. Though, a very important issue sometimes I just want to yell out to the crowd that it is my body and I am quite aware of my own biological clock and relationships status. Yes, eventually I do want to get married and have kids, but I KNOW about these issues. Telling me all the time does not make me feel better or encourage me to change my priorities. Believe me, I do not want to die alone either.



Economic Status

Because you’re constantly saving up and reinvesting back into your business, your financial priorities are different from most people. You have to make a lot of financial sacrifices. To most people, you just look poor. Unfortunately, a lot of people associate poor with unsuccessful. You will consistently be bombarded by concerned parties about whether you are on the right path or “maybe you should try something else” or “maybe it’s time to re-evaluate your career choices.”

Though all of these concerns are definitely valid, it ends up being a lot of noise that feeds into your self-doubt and it is an immense amount of pressure.




Hang with other entrepreneuers 

One of the ways I have found helpful has been surrounding myself with other entrepreneurs. Chances are, they are dealing with the exact same things too so it is nice to be reminded that what you are going through is perfectly normal and to get tips or just a sounding board.


Work in Public

I’ve found that forcing myself to work in public places too also helps. Though it is nice to roll out of bed and start working, being in public definitely helps to fight loneliness and can also be a good way to meet people. I am always working at various coffee places or bars. Some people work at co-working places and kill two birds with one stone as well.


Positive Reinforcements

You need to learn to consistently be honest with yourself about how you feel. Make sure you DO make time for yourself and life goals (besides work). Honestly, I am very bad at this, so I have had to treat “relaxing me time” like I would for any task, I schedule it in. Telling people to hold you accountable is important too. Remind people that you want to be a part of fun events even if our schedule is unpredictable and you cannot make most things. Joining a workout group or community is a fantastic way to keep in touch with different people on a semi-structured basis and to meet new people as well.


Crippling Self Doubt



Self-doubt is the worst. It can be utterly debilitating. And you will experience it ALL THE TIME. My life oscillates between extreme highs when I feel like I can conquer and solve any problem to self-crippling doubt when I think I am an absolute failure and have no clue what I am doing. Again, awareness that this is natural is often all it takes to snap you out of it.


Take a break...

Sometimes self-doubt is also your body telling you that you need to take a break. I find that when I run into writer’s block or it takes a lot of energy for me to do work that would normally take me less time, I need to just leave and walk away.  A shift in environment, new sounds, stimulation, people, can help to jump start those creative juices again.


Reconnect with other people...

Finding other people and reconnecting with old friends or simply co-working with someone can also help out. Self-doubt, in my experience, usually creeps up when we are at our loneliest. It happens because you are alone with your negative thoughts and negative thoughts tend to grow and fester.


Revisit Past Accomplishments...

Sometimes I like to revisit past accomplishments. I take time to update a resume, reel, or website portfolio, and I realize everything I have succeeded at and I’m reminded that I am moving forward, even if I may mentally not feel that way at that moment.


Revisit Goals...

Finally, writing down new goals and a to-do list may help to re-motivate yourself because you are visualizing yourself on your path to greatness!  




This doesn’t really get better. When you are an entrepreneur, things are always unpredictable. Clients are unpredictable, when you will get your next project or contract is unpredictable, etc. With time, you just learn how to better prepare for unpredictability. You save up cash for the bad times, you learn to use the downtime productively when you’re not busy, updating your website, creating marketing content, or organizing. It is always going to be unpredictable but I think you just learn to deal with it more effectively with experience and you don’t stress/fret about it as much.  

You hedge the unpredictability with side hustles. Sometimes I freelance on other people’s projects or I pick up a random task here and there, whether dog sitting or coaching a client. The beauty of unpredictability is that it throws you out of a state of comfort. As we know comfort breeds complacency. When you have to survive because you are out of your comfort zone, some of the best ideas come into light. I’ve picked up and revisited old projects that I had to put a pause on because work became too busy. I recently started a meetup/event for women entrepreneurs called Girl Boss Mafia.

As an entrepreneur the best way to deal with unpredictability is to embrace and go with it.

Final Words

Being an entrepreneur is rarely rainbows and sunshine. It is A LOT of hard work and sacrifice, but you do it because there is nothing compared to creating and building something you believe in. So embrace these turmoil of feelings you are going to face. It is perfectly normal. 


If you have any questions and want to learn more about turning your passion into a full blown career, find out here below: