How to Be Happier by NOT Working For Yourself, at Home, in your Pajamas

A lot of people will say you’ll be much happier quitting your job and going to work for yourself.quitting your job

This is the great American Dream, right? To quit your job and go and work for yourself. No boss to boss you around.

I think that’s all absolutely dead wrong.

Many people are more miserable working for themselves than they ever were working for someone else.

They may not like their job, and the pay may suck, but working from home may also be lonely, have low-pay and be completely unfulfilling.

It may be more dead-end than that dead-end job you just quit.

Don’t get me wrong. I’m actually not saying you should stay working in a job you hate.

What I am saying is if you want to quit your job to start a business or to go work for yourself, you should have a plan to grow into a real, fully-formed, larger business as fast as you can.

Your goal shouldn’t be to work by yourself, in your pajamas, in your bedroom for the rest of your life.

The Plan for Happiness


Your goal should be to apply principles that will grow your business from just you … to you + people working for you as fast as possible.

Of course, growing a small business into a medium sized business or larger is no easy task. It takes hard work, discipline, and a plan you implement strategically.

I know my opinion here runs counter to many other very vocal advocates of working for yourself. They say if you only will quit your job, you’ll be happier, make more money, control your schedule, and be able to explore new business opportunities.

Much of that is true. After all, I quit my job to start my own law firm.

However, I’ve never been truly alone. I work from an office with a dozen other professionals in my office suite, and I use a number of contract attorneys, virtual assistants, and other support professionals so I haven’t felt “alone” at all.  I also have plans to grow my business.

But let’s examine the benefits and drawbacks of each various option: (1) working for yourself by yourself, vs. (2) working for a company vs. (3) working for your own medium or larger company that you own.

1. Working for yourself by yourself

Pro’s: all risk is yours and all reward is yours; don’t have to deal with bad bosses and annoying coworkers; can keep overhead low to pocket profit; fewer distractions.

Con’s: can be lonely; low pay; lack of camaraderie; fewer opportunities for advancement; difficult to take a vacation or day off of work because no one else is available to handle the work while you are gone.

2. Working for a company

Pro’s: more stable, regular paycheck; greater camaraderie if you like your co-workers; more opportunities for teamwork; don’t have to deal with headaches like payroll, going out and getting clients.

Con’s: you’re working for The Man! low pay; bad bosses; annoying co-workers; risk of layoffs when economy turns down; fewer opportunities for pursuing opportunities.

3. Working for your own medium or larger company that you own

Pro’s: greater chances to scale the business; higher profit potential; possibility of building a “sellable” business one day when you are ready to sell.

Con’s: could be just as lonely; higher overhead could lead to low overall profits; could be just as difficult to take a vacation day if you don’t have a strong team in place.

Of course, a lot of your happiness is dependent on your personality. You need to know your personal profile to know whether you will be happier working by yourself, in solitude, or if you so crave being around people, you’d be better off working in a job.

Am I totally off on this? Am I crazy? Or do you agree small solopreneurs should set as a goal for themselves to grow larger?

Let me know your opinion in the comments below.