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Why You Hate Your Business (Advice for Freelancers & Entrepreneurs)

JessieUncategorized 2 Comments

There’s something we don’t talk a lot about in the online business space.

And it’s weird, because this thing is making our lives miserable. (Some of us, at least.)

What I’m talking about is the idea that “being your own boss” is inherently the best job in the world. That owning a business is freedom, and that anything short of entrepreneurship is laziness.

An incredible number of people assume quitting their day job will solve all their problems. But what do you do when the independent job you’ve created is actually worse than the traditional job you left?

In the 5 or so years that I’ve been working independently on and off, I’ve done a lot of things that sounded so good on paper but that I ended up… um, hating. ? And only now, with hindsight 20/20, am I able to see what had been going wrong and how I could have fixed it.

I asked some of my email subscribers, too, what they struggled with in their businesses. Their responses, combined with my own experiences, led to the article you’re reading here.

Today, we’re diving into how to create a career that fits you, and why so many freelancers and independent business owners suck at finding joy in their work.

Why you hate your business

Welcome to my office. I’m Dr. Jessie*, and I’m here to diagnose some of the most common business issues that make us feel disillusioned and desperate for a change.

So, what seems to be the problem?

* I am not a doctor. I know, shocking.

Problem 1: You’ve lost the work/home life boundary

Let’s start with the modern worker’s dilemma: not knowing how to leave work at work.

“Flexible” sounds so nice at first. Until you realize that it usually means “always working.”

If you don’t have a family pulling you away from your computer (or even if you do), it’s easy to find yourself working through lunch. Checking your phone through dinner. Getting that last task done in the evening.

I have to hustle to get this business off the ground, you tell yourself. Or, it’s the busy season.

And yet it seems like your business is always trying to get off the ground. It’s always the busy season.

Having a strong work ethic is great. But if your business isn’t keeping within normal working hours at least 90% of the time, there’s a huge opportunity here! I’m about to give you your life back.

Let this sink in: You don’t need to work nights and weekends to have a profitable business.

(Assuming you’re doing your business full-time.)

It’s absolutely possible to run a solid business in 8 hours a day—even if you just started it a few months ago.

I see a lot of folks finally hit a big monthly income milestone, only to realize that they can never do it again because that month absolutely killed them.

So how do you cut down your working hours without cutting down your profits?

Most people approach the issue from the wrong direction. They look at their tasks, try to cut out the fluff, and hope that their efforts will somehow shorten their day. (And then they’re flustered when a week later they’re up at midnight still answering emails.)

I like the Tim Ferris approach. In The 4-Hour Workweek, he recommends doing the opposite: Choose how long you want your workday to be, and stick to it. You’ll automatically be forced to get a lot smarter about your work.

Your brain is a problem-solving machine. Give it hard parameters, and it’ll find a way to work within them.

So I challenge you to log out at 5 every day. Close your computer. Or if you like to use your computer during your personal time, log out of your email. Turn off email notifications on your phone, and seriously consider deleting the email app entirely.

And just as important: Get serious about nurturing hobbies and activities that make you feel like a happy human, so those newfound free hours don’t feel like empty, wasted time.

Note that this cozy, Instagram-worthy scene couldn’t be possible without a CLOSED LAPTOP

And guess what? When you cut down your working hours, you may very well find that your work is totally unaffected. You’ll prioritize tasks automatically and still get the necessary things done every day.

But if things are falling through the cracks? Then that’s a sign you need to rethink your business model and/or prices. A business that makes you work longer than 8 hours a day to make a living isn’t a good deal, and you’d likely be better off getting a regular job. So, ask yourself:

  • What business activities bring in the most income for the least amount of time/effort?
  • How can you cut out the excess so you can focus all of your energy on those specific tasks?

Here’s an article I’ve written on this topic if you’d like to dig deeper: 5 Steps to Simplify Your Marketing (and Save Your Sanity)

But if you want to really dive into methods for streamlining your business, you should check out Ashley Gartland. She’s a business coach for busy entrepreneurs. To learn about her core ideas, I recommend looking her up on your favorite podcasts app. She’s done some great interviews over the years where she spills a ton of helpful knowledge.

Personally, I made my work my life for a long time. Oh, I took plenty of time away from the computer, but I always felt guilty about it. I’d forgo spending time with my husband or friends because I felt I needed to get more things done.

And then one day I looked up and realized that although I say my priorities are family, friends, and work in that order, I definitely hadn’t been living that way.

To be real with you—it’s still something I’m figuring out. I’ll probably share more about that in the future. But logging out at the same time every day and setting rules for the weekend has forced me to get smarter about my working hours and helped me develop a much more meaningful life outside of earning an income.

Problem 2: You’re not making enough money

Aside from flexibility, many of us start businesses because we hear how profitable it can be. When you’re in charge, there’s no limit to your earning potential. You can make as much money as you’re smart enough to bring in.

So we’re a bit shocked when, after months of exhausting work weeks, we’re bringing in less than we were before we took the leap.

What do you mean owning my own business isn’t an automatic path to riches?

As I just mentioned, stopping at 5pm can help. Not only will it force you to work smarter and get more creative, but it’ll also give your brain some real rest. And you’ll be much more likely to come up with fresh ideas and make smart business decisions.

But the money issue is multifaceted. Here are some more things to explore:

Changing up your sales and marketing. Let me be clear: If your efforts aren’t bringing in clients, then you’re not actually running a business. You’re running a dream.

(I say this lovingly, as I too have run some beautiful dreams.)

Every business needs two systems: 1) A process for getting in touch with people and 2) A process for convincing those people to give you money. (In an ethical way.)

If you don’t know how to get reliable results from these activities, then this is the area you need to spend some good time researching. When you’re done with this article, get Googling.

Raising your prices. If you’re a service provider, a good rule of thumb is to increase your prices every 3 projects or so. If that sounds impossible, then I’m guessing you’re not collecting testimonials.

Testimonials allow you to convince future clients that you’re worth the investment. Here’s a guide on how to ask for them: How to Ask Your Clients for Testimonials without Feeling Icky.

If you don’t know what kind of pricing is standard for someone with your experience and you’re afraid of overcharging—go find out! A lot of folks post their prices on their websites. Snoop on your peers. Join a Facebook group of others in your industry and ask the members (or just search for it in the group—I guarantee that “How much should I charge for ____?” has been asked a million times).

Changing up your offerings. Some offerings are more valuable than others. And this applies to both service and product businesses.

For example, if you love painting pictures of animals, it’s generally more profitable to sell custom pet paintings than to sell portraits of random dogs—and yet they both take the same amount of work.

But this all depends on your business and how you’re perceived. One person will make a lot more money by offering an all-in-one service, while another will be more profitable when they specialize. (And yes, this is a narrative that YOU can control.)

Two recommendations:

  1. Read up on “positioning” and “differentiation.” Again, get Googling. You might also check out the book Blue Ocean Strategy.
  2. Challenge yourself: Every morning, come up with 10 ideas on ways you could make more money. It’ll get hard fast. A lot of ideas will be crap. But I guarantee you that in forcing your brain to get creative, you’ll come up with some brilliant ones that’ll make your heart pound.

Problem 3: You’re caught up in things you think you’re “supposed” to do

I probably should’ve put this one first, because I get emails about this topic regularly.

The email typically goes like this: The sender started a business. They put a ton of effort (and/or $$$) into building a website. They’ve launched, the doors are wide open…

But they have no clients.

Usually, they’re asking me to help them improve their site to bring in more sales. And I get it! We’re told that websites are important.

But as someone who’s been in this game for a while, let me tell you now: Your website is not as important as it seems. Not at first, at least.

A website can enhance your outreach efforts. But it’s not going to bring in clients for you. In other words, the internet is not automatically directing people to your website. You have to take action every day to put yourself out there. It’s the networking, social engagement, relationships, and emails that actually win people over. (I’ve known many people who have built high-income businesses without a website at all! Though I admit it is good to have a simple site to give yourself a bit of credibility.)

Other things people get caught up in instead of actually going out and getting clients:

  • Taking online courses… and another one… and another one…
  • Blogging (this is an optional, long-term marketing effort that should go alongside your relationship-building sales efforts)
  • Starting a podcast (see “blogging”)
  • Taking on free clients more than 3 times (That’s my limit. Start charging something, even if it’s heavily discounted!)

There is a time and a place for each of these activities. But if you’re not bringing in enough money to keep the bills paid, they’re all just distractions. Your only task right now is to go make a sale.

Not to say this is all that matters. But uh, right now, this is all that matters.

Don’t know how to get clients? Find a Facebook group with other people in your industry doing work that’s identical or very, very similar to yours. Go to the side search bar and type in “get clients.” If the group is big enough, this will have been asked before, and others will have spilled their methods. Find a few techniques that sound appealing, then do more research on how to do those techniques well. Choose 1-3 to try. And really commit to them! It’ll be tempting to give up after a few no‘s, but most sales activities are just a numbers game.

If you’re a freelancer, you might get some benefit from my piece on 8 Ways to Get Your First Freelancing Client.

Get clients first. Then you can worry about your website and all the rest.

Problem 4: You’ve chosen the wrong business model

Working for yourself can look like a lot of different things. I mean, there are so many options regarding how you work and what you sell:

  • Products vs. digital products vs. services vs. affiliate sales
  • Subscriptions vs. one-time fees
  • Retainers vs. projects
  • Custom solutions vs. productized services
  • One big offering vs. lots of small ones
  • Marketing through direct outreach vs. content marketing vs. podcast appearances vs. just about anything

…Or any combination thereof.

I have this theory that a lot of us get introduced to the world of online business or freelancing by a certain person—whether it’s a friend or someone we see online—and we subconsciously assume that their way is the best way. So we try to follow in their footsteps… until one day we realize that their business model doesn’t work quite as well for us.

In this case, the only solution is to try out new business ideas. Experiment as widely as you need to—whether that means fiddling with your marketing process or trying out an entirely different career.

But experiment before committing whenever you can.

For example, I tried writing on Medium for 3 weeks to see if I wanted to be a full-time independent writer. (I didn’t, but I learned it was a great marketing channel.) I once took on a coaching client when I was still working full-time. I’ve experimented with selling different kinds of writing, selling my skills as an editor, being an artist, making videos, and promoting myself with cold emails. A lot of my experiments have been flops, but I always learned something.

Don’t limit yourself to the business that your favorite ✨business idol✨ has. They already made that business. And they did it because they figured out what works for them.

You’re only going to create a satisfying business if you keep digging inward and noticing what works for you.

Problem 5: You’ve sucked the joy out of what you love

This is the biggie.

How many of us started businesses around something we loved?

Maybe you wanted to spend more time doing graphic design, or cooking, or writing. So you started a business around your passion… only to find that now you’re stressed out of your mind.

Somewhere along the way, we all hear sayings like “find what you love and you’ll never work a day in your life” and “just follow your passion.” And we assume they mean “turn what you love into money.”

I’m all for finding work that doesn’t feel like work. You shouldn’t be dreading the work week. However, that doesn’t necessarily mean that you should be monetizing the thing you’re most passionate about.

Because monetizing your passion only works if you can continue doing that passion in the exact same way. (And even then, it can be tough.)

Take a hobby photographer, for example. She loves hiking on the weekends and photographing magnificent landscapes. She wishes she could do more of it, and has the idea to quit her job and start working as a professional photographer.

Cool! And when she tells her friends that she’s starting a photography business, they start sending her referrals. Except the referrals are for weddings, corporate portraits, and family photos.

But at least it’s photography, right?

So she takes the work, even though it’s not what she really enjoys. And one day she realizes that she’s just replaced her day job with a different one—and now she’s too tired of being behind the camera and editing photos that she rarely takes her camera along on her hikes anymore.

I searched “sad camera” to find this photo, and I wasn’t disappointed.

It sounds silly when it’s laid out like this, but it happens constantly. It happened to me with writing. I’ve always loved writing blog articles like this one. I’ve been doing it since college. So I assumed that since I loved writing so much, I’d enjoy writing blog posts for clients, too.

But I didn’t! Because I don’t have some endless love for writing content; I love writing primarily for personal expression. So instead of building a career around what I love, I built a career that sucked up all my writing energy.

So if you’ve turned your passion into your work and your passion is actually starting to feel like work (shocker), I’d prescribe one of these three solutions:

1) Streamline your business so that you can spend more time doing the activity you love and less time on admin, sales, etc. (This may require hiring an assistant, getting set up with a new business management software, etc.)

2) Get a job that lets you use your passion every day while someone else manages all of the other parts of running a business

3) Get a job unrelated to your passion, so you can do what you love in your free time without pressure

I go deeper into the topic of passion and finding work you love in my latest video:

It’s okay to admit that you hate your business

It can be incredibly difficult to realize that the thing you built yourself—the thing that was supposed to be your salvation—is making you miserable.

I was scared for a long time to tell you guys that I was no longer writing website copy.

But honesty is the only path forward. Running a business—or not!—can be a wonderful experience. Once you let go of the expectations from yourself and others (which are often just imagined, anyway), and you get real about what’s not working, you’ll be able to rework your path and create a career that’s actually satisfying.

Here’s to pleasant workdays and restful weekends.

– Jessie

Comments 2

  1. Thank you. Gave me some things to think about. I have grown to despise my very successful online industrial parts business and have thought about selling if I could get what it’s worth. Cutting hours wasted in the office and finding something constructive to do with the money will help I think.

  2. On paper I should love my advertising agency. I make over $240k a year working from home, only have one part time employee, only work 3-5 hours a day 5 days a week, and can dictate my own schedule inside of those hours. But the simple fact that everything is always on my shoulders, and I can NEVER take more than 2 days off in a row has drained me to the point where I feel like my only option is to shut the business down.

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