The dark side of entrepreneurship - 7 struggles & 7 ways to prepare

As I’m drafting out this post, I’m also getting ready for a trip 870 miles from home. (Yay road trips!) And it was this very trip that made me want to touch on today’s topic. Because instead of continuing on with the biz as usual and writing while on my mini vacay, I chose not to. I needed a break. A REAL break.

But… because I’ve committed to doing the damn thing, that meant I needed to front-load my work so I could take the time away. Which meant double-duty and less sleep for a bit 😅

This whole situation made me think about how being my own boss is great! Until it’s not. Sure, I get to take a vacation whenever I want! …but I also have to plan ahead, work ahead, and schedule ahead if I want to make it truly a work-free trip.

Why? Because it’s just me, myself, and I here… and these things aren’t going to get done unless *I* do them.

So I want to talk about the dark side of entrepreneurship. The things no one talks about. The things naïve little go-getters (like I was) don’t realize before getting themselves into this wild ride.

Because I don’t care how many people you see on social media on their private yachts, wearing designer clothes, driving fancy cars, and making millions each year… they’re the outlier. 

I’m NOT saying it’s not possible to get to that point. I AM saying there’s a lot of hustle and struggle and shit to dig through to get there. And we never get to see that side of it.

So in my little baby entrepreneur phase where I’m hustling, staying on my computer until bedtime (which is like 8:30 🤭), crying, stressing, and sometimes riding the struggle bus… I want to talk about the cons. The things that are hard. The things that test you and challenge you and make you wonder if it’s all worth it. 

Because yes, it’s good to be optimistic but it’s also important to be realistic. And when you truly know what you’re getting yourself into (or what you’ve already gotten into!), you can enjoy the journey more prepared and not only define what success looks like for you… but reach it. 

So… let’s dig in to 7 struggles and 7 ways you can prepare yourself in this exciting thing called entrepreneurship 😎

(Stick with me here, I’m not just a Debby Downer for this whole post, promise!)

The dark side

One. Loneliness and isolation

I actually think of this in two different ways.

First - Chances are, you’re physically working from home alone. While society wakes up, drives to work, spends the day in the presence of other humans, then drives home… you never leave home. Sure, you have your dog to hang out with while you work… and sure, you connect with people via email, Slack, or Zoom… but truly, it’s not the same as that in-person connection you used to get from the 9 to 5.

Second - as you’re changing, shifting, and growing into your new role… your existing relationships might be affected. You lose common interests with friends or they don’t understand why you would go through the struggle of starting your own biz. Whether it’s your intention or not, you soon find yourself feeling isolated from the people who once gave you support. It’s not that they’re doing it on purpose! They just don’t get it. They don’t know the things you’re going through anymore because it’s a world they’re not familiar with or a part of. 

Two. No more boss

Yup, you’re your own boss now! No one tells YOU what to do! 💪🏻

Which sounds amazing at first, and it is, but you now have a LOT of extra responsibility that you didn’t have before. Literally everything depends on you. No one but yourself is going to hold you accountable anymore.

You make your schedule. Want time off? You have to plan ahead and front-load your work (unless you’re at the point where you’ve got things running on evergreen or have a small team. #lifegoals)

You make all the critical decisions regarding the direction of your biz - your purpose, your mission, your goals, your services, your target audience… finances, communication, marketing, sales, customer service… See what I mean? No one from another department is going to email you telling you what you need to do anymore. It’s all on you now.

Three. Endless shifts and challenges 

The digital world we live in has benefited us in so many ways, but it’s also created a volatile space for entrepreneurs. If you’re looking for consistency, stability, and comfort… this ain’t it. Think about how quickly things change now. It’s like we can’t even get used to the way things are before there’s another “upgrade.” Social media algorithms change, AI threatens to take over, consumers are sick of being sold to… there are a number of factors that are going to affect what you do and how you do it. And the things you’re planning on doing now may not work or be relevant in a year. Or less 😬

You’re going to face challenges and have obstacles thrown in your path. You’re probably going to have to pivot a few times too. But as long as you know this ahead of time, you’re solid. When entrepreneurs get started with their mind set on one thing and one way of doing it and are unwilling to shift when the world shifts around them… that is when problems arise. You need to be ready, and willing, to adapt.

Four. Mental health, stress, and anxiety

Check out this powerful stat from the National Institute of Mental Health: 72% of entrepreneurs are directly or indirectly affected by mental health issues compared to just 48% of non-entrepreneurs. That’s not a small number.

Entrepreneurship can be the perfect recipe for high levels of stress. Being your own boss comes with a looming responsibility and pressure to get everything figured out and done the right way, and hopefully, on the first try. Your income might become unstable, you may work prolonged hours trying to get things done, and your relationships and personal wellbeing might start to suffer. Multitasking, juggling deadlines, working through finances, managing the workload, and trying to keep your head above water during new or challenging situations can cause a lot of stress and worry. 

Five. Work-Life balance

Oh, my friend, the struggle is real with this one!!! With a 9-5, you clock out and your day is done. With entrepreneurship… it SHOULD be the same concept, in theory. But so many of us have a haaaard time creating that hard stop at the end of the day. A never ending to-do list, lack of vacations, multitasking, and being responsible for too many things create constant pressure and make it easy to just keep working until things get done. But they never get done 😅

You might find yourself answering emails in the evenings or on weekends, opening up your laptop just to do “a few more things,” or taking phone calls during family time. You have even put boundaries in place, but keeping to them is a whole different challenge. This especially becomes hard when you don’t leave home for work and don’t have that physical transition from one part of your day to the next. The lack of balance here can lead to burnout, exhaustion, and a lingering sense of overwhelm.

Six. Constant learning and adaptation

Okay, so as an ex-teacher, I’m actually used to this and personally love it. I hate sitting still and I love learning new things. BUT I know this is not the case for many people, so I’m including it. Because this isn’t about me!

We already touched on how the digital world and the way society works is always changing, which means to stay competitive and relevant in your field, you have to make sure you’re keeping up with the times. Trends change, technology advances (and rapidly, it seems!), and consumers don’t buy the same ways they used to. This often means you’ll be seeking professional development, learning new skills, gaining insights and knowledge related to your target audience… and the work is truly never done.

Seven. Uncertainty and financial risks

I’m not really huge into finances and all that money stuff, but as an entrepreneur, it’s soooo damn important to have your money straight. There’s no more security of the 9-5 paycheck and  your biz isn’t guaranteed to succeed.

Entrepreneurs face the reality of limited security and stability compared to traditional employment. The success of their business is not guaranteed, and they may face financial instability or even business failure. This lack of stability can create anxiety and fear, especially when it comes to long-term planning and financial security.

…not me low-key freaking out at all the stuff I just wrote because it pertains to me too.

Can there please be a bright side?

Yup 😉

The bright side

But let’s not make this all doom and gloom, yea? I’m not bringing all this up just to poo on your entrepreneurial parade. Not at all!!! 

This is about being informed, so you (...we) can be prepared.

So along with highlighting some of the dark things in this journey, here are some ways to make sure you get through the struggles… because you’ve got big ideas and the world needs YOU.

One. Build a strong support network

Having people in your circle who get you is so important. Surround yourself with other entrepreneurs who know what you’re going through and who you can learn from. The guidance, advice, and encouragement is going to be SO damn important for helping you get through the tough times!

Join communities and Facebook groups, attend in-person and virtual events, and find a mentor or two. Networking, building a strong support system, and even making new entrepreneur friends can help you stay motivated and feel seen and supported. 

Two. Create a solid business plan

Make sure you understand what it is you want to do and how you’re going to do it… with the understanding that you might have to be open to change. Set goals (yearly, quarterly, and hell, weekly!), decide on your strategies, identify the skills you have and will need, create your offerings, decide your target audience, and figure out your budget. Having all of these things in mind will make getting started easier and help guide you during challenging moments.

Three. Manage finances wisely

Don’t just quit your job and start a business without planning ahead and saving up some money!!! Before even beginning, it’s often advised you have 3-6 month’s worth of living expenses saved up before you leave your 9-5. Once you begin, you’ll have other finances to keep in mind, you know, all the costs that come with running your biz. Make sure you keep track of all expenses and keep to the budget you made in your business plan. If things are a little overwhelming (especially during tax time 😪), get professional advice instead of trying to figure it out yourself. It’s worth it.

Four. Seek and appreciate feedback

Accepting feedback is such a necessary part of being a successful entrepreneur! Make sure you’re always asking for feedback from your community, and then actually listen and implement what you’re hearing. Caring about what your clients/customers have to say helps you improve your services and create offers they actually want AND need. It helps you understand what you’re doing amazingly and what you need to give a little more love and attention to. And when your community sees how you care and actually take their thoughts into consideration, you’re just building more trust and loyalty with them!

Five. Develop resilience 

Resilience is the ability to bounce back from failure… and you, my friend, see failure as a GOOD thing. Failure means you’re innovating, trying new things, and growing, and best of all, they’re the most valuable learning opportunity you’ll ever experience. Nothing teaches us better than when we learn from our own failures, right? 

Don’t let fear of failure set you back, cause you to procrastinate, or keep you playing small. Be willing to step outside your comfort zone knowing damn well that you might not succeed the first time. But the next time you try? You’ll be a hell of a lot better! 

Six. Prioritize self-care

No, I’m not talking about cucumber slices on the eyes during a bubble bath here… unless, that’s what you’re into. Self-care is much more involved than that. It’s making time for exercise, eating healthy, getting enough sleep, managing stress, engaging in hobbies for FUN (not for your biz!), and taking time for rest and relaxation. 

Start scheduling regular breaks for yourself, both small ones during your work day AND larger breaks away from everything. Even if it’s just for a day. Make it a priority to give yourself a vacation. Make time to connect with friends and family. This whole biz thing will never succeed if you’re not taking time to focus on YOU and the things you need first.

Seven. Celebrate small wins and milestones

You deserve to be recognized and celebrated! No matter how small an achievement might seem, you better start celebrating it! If you’re only focusing on the end goal, it’ll seem like you’re never making progress and you still have so much to accomplish. Break your goal down into little baby goals. Acknowledge your progress, celebrate the steps you’ve taken, and give yourself some praise for all the great things you’ve already succeeded at! Your mindset is huge, and this will help keep you on track to meeting ALL those amazing goals you set for yourself.

Despite all the negative aspects of entrepreneurship lurking in dark corners, something pulled you into this new world. Something convinced you that this was your path. Maybe it was the promise of freedom (financial, location, schedule, whatever). Maybe it was the opportunity to reach more people and make a difference in more lives.

Don’t let the challenges prevent you from even starting. Familiarize yourself with the struggles that are likely to come and go at it prepared. You’re strong, you’re determined, and you’ve got a gift that the world needs! 

And if you haven’t grabbed this yet, this free guide helps you get started with writing story-driven emails to your community… the kind of emails that build trust, create genuine connection, and grow your biz 😉

Now, I’m curious… What part of entrepreneurship is the hardest for you?