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Six ways to help struggling entrepreneurs get through the grind

Editor’s Note: The following series New Orleanial Tech Entrepreneurship is a week-long series curated by Mary Pwint as part of the Digital Research Internship Program in partnership with ViaNolaVie. The DRI Program is a Newcomb Institute technology initiative for undergraduate students combining technology skillsets, feminist leadership, and the digital humanities.

As technology advances and New Orleans joins the movement to innovate for a better future, let us appreciate the tech entrepreneurial spirit and energy that New Orleanians share. This grouping of articles explores and appreciates tech entrepreneurship in New Orleans as it relates to tech celebrations, gatherings, startups, and inspiration. For the final day of our “New Orleanial Tech Entrepreneurship” series, here is some motivation struggling entrepreneurs get through the grind. This article was originally published on Apr 13, 2017.

Big Ideas for the entrepreneurial spirit.

Being a startup founder has a built-in, perceived image of glamour: the wild, overnight success that leads to dream houses, foreign cars, exotic vacations with superyachts and landing on the cover of Forbes.

While it might be natural to aspire for those things as entrepreneurs, the reality is that most of us are not overnight successes. We are starting our companies with our own money (which is often very little) under conditions that are anything but glamorous. We’re sacrificing a lot for hopeful success. Contrary to popular belief, it can be embarrassing, isolating, and at times just plain miserable.

I started my company, DreamStarter, with just an idea a year and a half ago. At that point, I was working part-time as I pursued my MFA in Advertising. Things were already rough as a “poor art student” so adding “self-funded entrepreneur” to the mix really thrust me into the unglamorous startup life. Yes, dinner often consists of a can of Chef Boyardee ravioli. I rarely go out because I can’t afford to, so I don’t see my friends as much as I used to. I rent in a low-income neighborhood where I’ve found a homeless man passed out in front of my doorstep more than once. A few months ago I was mugged at gunpoint several blocks from home.The struggle is realer than real.

While not everyone may experience this level of hardship when starting their companies, there is always some form of struggle we face in pursuit of our endeavors. These shadows can certainly take a toll on our mental, physical and emotional health. They’re often the unspoken doubts, fears, and obstacles that make us pause and think “should I even keep doing this?” “maybe I should give up” “this isn’t worth it anymore” “I’ll never be successful.” It’s easy to run out of positive counter-arguments to thoughts like these and even easier to let them eat you up inside.

So how do you press on, even in the face of all of the adversity? Keep your head up when you have your head down.

  1. Reconnect with your second reason for becoming an entrepreneur. We all know that reason number one is “I’m going to change the world” but on bad days, that can be overwhelming. So, ask yourself, what was your second reason? Maybe you wanted to build something your kids would be proud of, or you had a personal goal to never work for anyone else again. Maybe you wanted to be able to buy a new pair of designer shoes every month or splurge on that superyacht one day. My “second reason” is actually giving my dogs a better life! I want to live in a bigger space with a real back yard for them to be able to run around play in one day. Whatever your reason is, keep it front of mind. Put up a picture of it. Keep it out at all times or take it out when you’re on the verge of an entrepreneurial “ugly-cry” moment. Put your focus there for a few minutes and then get right back to your grind.
  1. Put YOU on your calendar (and don’t stand yourself up)! I live by my Google calendar and some days I put events on it that are not work-related, but “me-related” like “6 PM: LONG, LUXURIOUS BATH AND WATCH TV!!!” It’s just nice to see something fun or relaxing listed at the end of a day filled with meetings, phone calls, and other mundane business tasks.
  1. Change the subject. As a struggling entrepreneur, it’s normal to be constantly asked that dreaded question at every party or gathering, by every friend or family member: “how’s your new business coming along?” What a lot of non-entrepreneurs don’t realize is that sometimes very little “milestone” progress is made on a startup between now and the last time they asked, despite how hard you’ve been working. It can feel sucky not having much of anything “new or cool” to say on the topic, and it’s particularly hard if things have hit a rough patch. Do what I do to avoid the downward spiral of entrepreneurial shame: give a short, polite answer and change the subject, “I’m still plugging away at some issues, but overall things are moving forward. How’s your new house coming along?” Works every time.

“Struggle is just the unglamorous form of progress.”

  1. Make friends with other entrepreneurs. You’ve probably already figured out that as much as you love them, your significant other, best friend, grandmother, cat, etc. don’t really know how hard being an entrepreneur is. To them it may seem like whining when you express your struggles but other entrepreneurs know what’s up. Try to join or organize a monthly get together with them through or your local accelerator. I actually created DreamStarter for this reason. For all the lonely and confusing moments, when you just want to anonymously connect with other people going through the same thing – whatever that may be. Venting can be good for the soul. Inspiration and encouragement from peers and experts is crucial to keeping your dreams alive.
  1. Make peace with the idea of possibly changing your idea or approach. If things are not working out and/or continually making you feel bad, at some point you’ll need to cut your losses. That could mean switching your startup’s direction, or even just starting over all together. That’s scary, right? No one wants to be a quitter or lose everything they’ve worked so hard for. But if it’s really taking a toll on you, there’s no sense in both you and your idea suffering long-term. Find comfort in the notion that, out of the ashes, a better idea can be born, or it could lead to a new plan, path, or venture.
  1. Give yourself a deadline. Amidst my own struggles, I’m giving myself until March 2017 to figure out my next major move with DreamStarter. At that time, if nothing significant has happened, I plan on letting it go and moving forward with a couple of other completely different ideas. I no longer look at the possibility of a DreamStarter “death” as a failure, but rather the rebirth of something else. Give yourself a deadline, and then move forward. Have faith, but don’t get stuck on “one and only one” outcome. Don’t let your ego get in the way of your success – or your health and happiness.

The main thing to remember as a struggling entrepreneur is that you’re not alone. Plenty of us aren’t “there” yet. It doesn’t mean we’re incapable, wasting our time, or failing. Struggle is just the unglamorous form of progress.

Arielle Jordan is a native New Orleanian and the founder of DreamStarter, a new “social chat-work” that allows users and experts to connect in real-time chat rooms around specific problems, topics, and goals. Learn more at


This article was originally published on The Distillery, a NolaVie content partner. 


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