Top solopreneur challenges and how to fix them

Let’s first tip our metaphorical hats to the elephant in the room.

Solopreneuring is hard.

I know that’s not what the floppy-hat wearing, hammock-lounging, margarita-sipping boss babes on Instagram want you to believe, but you and I both know better.

We know about launches that flop, servers that crash, and designers who ghost you mid-project. We know that what we’re passionate about is 5% of what we do, and the other 95% is bookkeeping and trying to figure out why the contact form on your website still isn’t working.

We also know it’s better than any job we’ve ever had. That’s why we keep showing up, even when it’s hard.

I see that some of you are struggling though.

I looked into my crystal ball (a.k.a. my gmail account and the Six-Figure Systems community) and I see that solopreneuring is, in some cases, starting to wear thinner than Uncle Bob’s combover. I also see that there are four primary causes for your frustrations.

Here’s how to fix them.

Overthinking

Overthinking is the mental equivalent of Bill Murray in Groundhog Day. Every day, you wake up in the same place, ruminating over the same choices, and making no progress toward your goals.

Here’s what overthinking can look like for solopreneurs:

• You’ve rebranded three times in the past year, and this one doesn’t feel quite right either. You’re thisclose to going back to your original idea.
• You’ve spent months learning, and every book and course and webinar seems to contradict the one that came before it. You’re constantly in search of the one that will finally make everything clear.
• You’ve changed course platforms multiple times, investing $$$ and time in learning the ins and outs of each one, yet they all fall short.
• You’ve recorded your course videos six times, and each time something isn’t quite right. The lighting is weird, the volume is too low or too high, your shirt clashes with your background, one of your slides has a typo… you get the idea.

The solution to overthinking: Take the next step.

The problem with high-achieving, overly-ambitious entrepreneurs like us is that we don’t allow ourselves to ever get it wrong. Mistakes are something we can forgive in others, but never in ourselves.

That kind of perfectionism leads to overthinking. The only way out is to accept that the next step might be (probably will be) the wrong one, and to take it anyway.

Tell yourself, “It’s good enough for right now,” and then keep moving.

Your branding is good enough. It’s time to stop messing with your messaging and start putting yourself in front of potential clients. Are they your perfect client? No. But you can’t know who your perfect client is until you work with a few less-than-perfect customers.

You’ve learned enough for now. It’s time to pick one path and start implementing. All of those contradictory bits of advice you’re hearing will begin to make more sense once you start moving and can see the bigger picture.

Your course platform (and that recording) is good enough. Finish creating your course, get it uploaded, and start selling it. Your community will care less about the quirkiness of the platform than they will about the results you provide, so start providing them.

Bottom line: All platforms, strategies, and brands work if you stick with them. What’s keeping you stuck here isn’t substandard resources or imperfect branding, it’s a lack of implementation.

Take the next step.

Meaningful feedback

Showing up and getting to work is great advice. But how do you know the work you’re doing is the right work, or good work, or payment-worthy work?

That’s where meaningful feedback becomes more valuable than a couple dozen eggs.

Feedback helps keeps you from leaping before you’re ready—or worse, putting off your launch when you are. Feedback helps you fill in the gaps to make your course or membership more useful. Feedback can even help you come up with attention-grabbing titles.

Yet so many of us work in a digital vacuum, with no one to offer advice but the cat.

The solution to not enough meaningful feedback: Cultivate a circle of business besties.

Even better, cultivate a circle of business besties who will actively poke holes in the ideas you love the most. Any friend who can look you in the eye and say that your idea for hop-through toad wash franchise is “Brilliant!” is not qualified for this important job.

Look for those who will tell you the truth, and invite you to stretch your imagination and comfort zone a little bit.

No business besties to call on? Consider joining a mastermind group, a paid forum, or hiring a coach.

Right now, you may be thinking, “But Cindy, I can’t possibly share my toad wash plan with anyone! What if they steal it?”

First thing you need to know is that ideas are about as useless (and abundant) as grains of sand. It’s not the idea that matters, it’s the implementation of it that counts. Anyone who would steal an idea (if that’s even possible; see my next point) is unlikely to do anything grand with it. Even if they do, your implementation will be different and better.

Ideas are also everywhere, and with very few exceptions (the iPhone comes to mind) they have mostly all been done before. That’s a good thing, BTW. It proves viability. It’s when no one has done a thing that you need to be concerned. There’s a reason hop-through toad wash franchises are not a thing.

Stop worrying about someone stealing your ideas, and get to work implementing them. If you need feedback (and you do), cultivate your circle of business besties to support one another.

Time management

Call it a lack of motivation, or discipline, or procrastination, or whatever. The fact is, time slips away from you. One YouTube short turns into 30, and before you know it, an hour is gone and you still haven’t written that email. (It’s not just me, right? Right?)

It’s not only YouTube though. It’s the laundry, the grandkids, lunch with your sister, a doctor appointment, or just a lazy kind of day.

The problem with time management and entrepreneurship is simple: There’s no accountability.

Sure, you want to create a course or write a blog post or launch a podcast, but there’s no real deadline. No one is waiting on you to get it done. It won’t hurt to wait until tomorrow to start. Or next week, or next month, or, heck, why not wait until fall? I mean it’s practically summer and the kids are going to want to go to the beach, so why start now?

Sound familiar? I’ve worked with clients who have been letting themselves get away with this kind of loosey-goosey time management for years, and you know what? They eventually give up on business completely.

Now listen. There’s nothing wrong with deciding entrepreneurship just isn’t for you, and hanging up your “boss babe” floppy sunhat once and for all. Kudos to you for recognizing you’re just not that into running a business.

But if you are that into it, there’s only one thing to do.

The solution to time-management struggles: Treat your business like a job.

I know, I know. Your business dream exists because you don’t want a job, but hear me out.

As I write this, it’s 5:49 PM on Saturday evening. Do I want to be writing this post on a Saturday evening, or would I rather be sitting out on the patio enjoying another beautiful Arizona sunset and sipping a glass of wine?

I’ll give you a hint: 🍷 + 🌅

But it’s my job to publish content about online business building. That’s how I get paid. Instead of waiting to feel inspired or letting every little thing distract me from doing what I’m paid to do, I am treating my business like the job it is, and I’m sitting my butt in the chair until this draft is done.

As someone famous once said, “Inspiration is for amateurs. The rest of us just show up and get to work.”

Some of the ways you can treat your business like a job include:

• Have set working hours. Yes, I totally failed at this one today, and that’s ok. I am a work in process, too.
• Create a regular publishing schedule. This post is due on Monday, which is why I’m working on Saturday evening.
• Have a dedicated office space. Working from the patio sounds great to me, but the reality is I get nothing done. If I’m out on the patio with my laptop, know I’m scrolling Facebook, not actually working.
• Set implementation intentions for yourself. A simple way to do this is to time-block your calendar.
• Create and stick to your deadlines. If you have trouble with that, work with an accountability partner or coach.

But maybe it’s not that you don’t manage your time well. Maybe it’s simply that you don’t know what to actually do with your time.

Lack of Direction

Back in 2009 or so, I had the idea that I was going to start an online business. I had zero money (recession, remember?) so I watched every free webinar I found. I read blogs and signed up for email lists and soaked up all the knowledge I could find.

Every day, I’d sit down at my computer and “work on my business.”

And every day, I’d do exactly nothing. Not because I wasn’t motivated. Not because I didn’t have the time. Not because I didn’t want it badly enough.

I simply didn’t know what direction to go. For all the information I’d consumed, I still didn’t have a clear path.

The solution to a lack of direction: Start with your why.

I’m not talking about a Simon Sinek, change-the-world level of why, but rather your personal reason for starting a business. Typically, it comes down to one of four things:

1. Money, as in, you need some. I certainly did.
2. Autonomy and time freedom because you’re sick to death of your nosy boss peering over the top of your cubicle wall.
3. Service to others who need your expertise.
4. A creative outlet—or in other words, a self-supporting hobby.

Each of those reasons dictates the direction you should go, and can even eliminate the overthinking that comes from having too many options.

If your why is that the car needs a new set of tires and the bank wants their mortgage payment and you can’t cover both, the direction you take will be very different than if you simply enjoy creating pretty designs in Canva and have discovered it’s possible to get paid for them.

I used to think I needed a “hero’s journey” style why. I was embarrassed to admit I started a business for the money, but that’s exactly where I was in the beginning. I needed to pay the mortgage, and I was concerned about the security of my day job.

Once I figured that out, direction was easy. I needed money, and the fastest way to get it is to work for other people, so that’s what I did. The direction I needed to go? Outreach to potential clients and networking with others who could refer me.

If you’re struggling with direction, consider your why. Be honest with yourself about what’s driving you, then forge your path based on that reality.

Frustration is part of the process

I wish I could tell you that running a solo business is all beaches and blue skies, but honestly, you’re going to run into plenty of frustrations on whatever path you choose. Contrary to popular belief, the struggles don’t make the journey less appealing. They make it better.

Hit me up in the comments and tell me what you’re struggling with right now. Not only would I love to hear from you, but I’d also like to understand what’s most frustrating for you, so I can create better resources to help.

If you’d prefer not to share publicly, feel free to email me at cindy@cindybidar.com.