Why It’s Harder To Work For Yourself Than Someone Else

Are you dreaming about leaving a traditional job to work for yourself? Some people excel at self-employed entrepreneurship. They inspire us and make it look so easy. Yet others quickly crash and burn even with great ideas and the best intentions. Let’s find out why it’s harder to work for yourself than someone else sometimes.

As alluring as breaking away from the traditional workforce may seem, working for an established company as a W2 employee has its perks compared to being self-employed or part of a family business.

Is entrepreneurship worth it? While offers freedom and control, it also involves major risk and effort.

Benefits of Working For Someone Else Vs Yourself

Reduced Financial Risk

With a traditional job, you earn reliable income without really worrying whether the business will succeed or fail. Established companies with solid track records for profits and longevity provide far more stability as well.

Every two weeks, your paycheck hits your bank account automatically like clockwork. Even if you make a costly mistake at work that loses the business money, as long as you don’t get fired, you’ll still get paid just for “showing up.”

On the other hand, entrepreneurs often face years without profits. It’s no wonder there are such high failure rates.

Even family businesses see fluctuating results based on economic factors. But large corporations or public sector jobs offer less volatility.

More Focused Responsibilities

Traditional jobs enable specialization. Employees focus on simply fulfilling their individual role’s duties versus tackling a huge range of essential business functions. The workload can still be high, but it’s typically more streamlined. This allows workers to develop and apply specialized, niche skill sets to their jobs. It’s an efficient way to run a business when you have lot of employees to fill specific roles.

On the other hand, working for yourself or a family business can be very overwhelming. With only yourself, maybe a spouse, or a few other family members to do all the work of an entire company, there are a ton of “shoes” to fill without a lot of feet!

Entrepreneurs have to juggle everything from the product(s)/trade/service itself, strategy, marketing, analytics, financing, operations, PR, customer service, and more. It takes a mastery of specifics to have a smooth oiled machine. A day job is so much easier than entrepreneurship!

Family enterprises also involve wearing many hats and answering to relatives. And we all know how complex family dynamics can be. If you don’t believe me, just watch any old episode of Gordon Ramsey’s reality show Kitchen Nightmares where he steps in to help many family-run restaurants that are in a crisis. Talk about stress, dysfunction, high emotions, and lots of screaming matches.

Sure, you can outsource certain tasks, but that’s not always as easy as it seems.

Less Personal Sacrifice

In order to launch or keep their businesses afloat, entrepreneurs may have to take a cash-out refinance on their homes, drain savings, and sacrifice family time getting ventures off the ground.

Imagine putting so much of your own money into your own business just to launch, then having to pay even more money to keep the lights on, only to end up with a failed business and no money left to your name – or even worse to be broke and buried in debt.

As an employee, however, if the company you work for has a bad quarter or loses a big client, you don’t have to make any personal sacrifices to your own finances to make up for the losses.

Sure, if business gets really bad you could lose your job altogether, but at least you can still collect your salary the entire time you’re employed. And you could also try and negotiate a severance to get paid to leave and find something better.

Better Work-Life Balance

The demands of self-employment or managing a family business also create stress. But with a typical job, you can typically clock in and out without business tasks overtaking your personal life.

Don’t get me wrong, work-life balance can still be a huge challenge when you work for someone else. I certainly had my share of sleepless nights and an eventual mental break down when I worked a traditional office job.

But the boundaries between work and home are a lot clearer when you work for someone else’s company. Less overlap means it’s easier to compartmentalize your life work and at home.

Built-In Infrastructure

Self-employed rockstar freelancers and startups require building systems, processes, and infrastructure from scratch. Family ventures can do the same or cling to outdated technology and workflows.

But most major corporations and public agencies invest heavily into new technologies and frameworks for success. So as an employee, you simply plug into efficient settings that are put into place for you. Infrastructure liftoff responsibilities are usually absent and taking place behind the scenes.

My Own Challenges Working For Myself Versus Someone Else

While I wish I could say I’m a huge success and the type of person who makes self-employment look like a breeze, I can’t. I’ve had some great moments, and a lot of ok ones, but I’ve had more bad times than I would like to admit.

Here are just a few examples of why self-employment and working for a small family business has been harder for me than working for someone else sometimes.

Distractibility

It wouldn’t surprise me if I have some degree of ADHD. Although I do have the ability to focus on a task, my mind is often cluttered which can impede me from staying focused for long periods, and I get distracted very easily. Advertisers would love me as a consumer because one glimpse of a commercial or ad out of the corner of my eye and I can’t help but stop what I’m doing to watch it.

I also have a weakness of not following all the way through on tasks because I have too many things going on at once and start doing something else before I finish what I started, which often isn’t intentional. I can’t count how many times a day I’ll ask myself, “wait what was I trying to do just now?”

Fewer deadlines

When you work for yourself, you often must be disciplined enough to set your own deadlines. Due to my tendency to get easily distracted, I’m really bad at setting clear, consistent deadlines for myself. When I had a regular office job, my work was filled with deadlines. I hated them, but I didn’t have a choice. I was under pressure to meet if not beat them.

The autonomy and flexibility that come with self-employment are priceless. But without enough self-discipline to create my own deadlines consistently and stick to a regular structured routine, it’s no wonder my progress is terrible.

Related reading: Freelancing exposed: the pros and cons of self-employment

Less efficient

When it comes to work that I partner on with my spouse, my level of efficiency is ridiculously lower. Even though he doesn’t like to admit that he’s well above average in terms of productivity and focus, he is. Meanwhile, I think my efficiency is average at best, but probably below average. That dichotomy can be quite frustrating for us both.

When I worked at my last traditional day job, the deadlines forced me to work on my productivity. And with client work, I have to demonstrate that the hours I bill are producing enough substance and value for them to stay in business with me.

Conflicts of interest

Remember how I mentioned above that family dynamics can cause all hell to break loose when emotions and different intentions get in the way? Anyone who works with a family member, or a best friend, can tell you these dynamics are much harder to juggle than working with coworkers you have no emotional “baggage” with.

Most coworkers in a corporate environment will stay civil and respectful with their communication. It’s much less emotional, way less heated. Yes, there are plenty of things that may annoy, frustrate, or piss you off at a corporate job, but you have to stifle those emotions to save face. Otherwise nobody will want to work with you and you’ll be put on the chopping block.

When your colleague(s) include the closest people in your life, however, those filters tend to get thrown out the window.

Fewer resources

I wear so many hats now in the work that I do, I can’t even write them all down. There are no other departments I can go to for help or subordinates I can assign tasks to when I’m sick, my kids need me, or I’m snowed under. I have to troubleshoot endless things solo without help.

Payroll’s messed up? That’s on me to fix. Vendor suddenly charging us double? I have to make calls and sort it out. Customer wants a refund? I have to review their case and process it myself. Audio file needs editing? I have to splice it and stitch it together myself. Broken plugin? I have to research and troubleshoot, etc. etc. etc.

My Journey In Self-Employment Continues

Even though I constantly feel spread too thin, have a frequent overlap of work and family, and must push through intense emotional tensions sometimes, I still prefer self-employment to traditional work.

Am I better at working for someone else? Yes. Am I too stubborn to change? Probably. Can I mirror the self-discipline I have with meeting someone else’s deadlines in my own business? I must!

This has been a bumpy year for me. I’ve had to help my mom with some international family matters that are still ongoing. This has taken months out of my life that I could have put toward my business and spent on so many better things. Emotional stress from my mother, our complex relationship, and endless added responsibilities thrown onto my shoulders really negatively affected my mental health this year.

I also had to juggle a lot of uncertainty, home maintenance and repair stress, and squeeze in a relocation which is very time consuming with two young kids. Plus our childcare situation changed a lot this year, so I’ve been juggling a lot more things in general with less help.

Nevertheless, I do feel really grateful despite all of life’s challenges. I expect there will be a lot of long hard days and nights in store until the end of the year and throughout 2024, but I’ll be pushing on through.

And as I like to say, sometimes you just have to pause and give thanks. Who knows, you may just lookup and see a rainbow.

Working For Someone Else Is Easier Than Working For Yourself

To wrap this up, traditional employment lets workers focus on their individual contributions without really worrying if there’s enough money for the company to pay the electricity bill or if the business can stay afloat.

Having access to established and improving infrastructures and new technologies also make it easier for employees to focus on their tasks at hand without all that “background noise.”

Having a focused and limited scope of responsibilities also reduces risk and sacrifice compared to the all-in nature of self-employment, entrepreneurship, or family dynamism.

While a lot of corporate jobs may lack glamour and the benefits of ownership (equity), they offer stability, simplicity, and better work-life balance. Which a lot of people would agree is a great trade-off!

Related reading:

Financial Advice For Self Employed Solopreneurs And Side Hustlers

10 Best Reasons Why You Should Start An Online Business