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Moving to Self-Employment: More Fun or More Work?

The following is a guest post from Robert Farrington, who writes at The College Investor, a personal finance blog for young adults.  He is starting a new venture to Beat the Nine to Five, where he is chronicling his journey to make the jump to entrepreneurship.  You can get a free copy of his Quitters Checklist, the ultimate guide to quitting your job to become an entrepreneur. 

A lot of people dream of the day when they can call it quits at their job and head out on their own.  Crystal did it over a year ago.  In fact, a lot of bloggers have made the jump to self-employment.

However, one question always arises when moving to self-employment.  Is it more fun, or is it just going to be more work?  The answer isn’t an easy one, but here are some things to consider about leaving your nine to five job and moving out on your own.

The Pros of Self-Employment

The dream: all of the positives of self-employment.  Lifestyle engineering…  Working from a laptop on the beach…  No boss to answer to…  Whatever your dream is, there is no doubt there are a lot of positives that come with getting out of the rat race.  However, it also depends on what type of business you are in.

I believe the biggest perk is freedom.  It’s something that confines you in your day job.  You can’t sleep in late – you typically have to follow office time.  You have certain tasks you must do, and there is a strict order to operations.

Along the same lines, lack of freedom means rigidity in where you work.  You typically have to be in the office.  You have set meetings that require your presence.  All of these things can potentially disappear with self-employment.

It moves to you setting the terms.  Yes, you still have to earn an income, but you have more flexibility in your work hours, your work location, and even when setting up meetings.  And while the client comes first, they don’t need to know you’re taking that conference call in your pajamas from your coffee table while catching up on last night’s television shows.

Finally, that freedom of self-employment means that you only report to yourself (and possibly your family).  No more boss breathing down you next, no more annoying co-workers chewing gum loudly in the next cubicle.  No more decisions you disagree with.  It’s just you.  If you don’t like something, you can change it.

The Drawbacks of Self-Employment

However, that last part is also the biggest drawback of self-employment.  It is just you.  That can add a lot of stress to the mix, something that you might not have experienced before at your nine to five job.  The buck does stop with you, and your choices can have a profound effect on your success or failure.

And on that note, your freedom will slowly escape you.  You have to find clients, build relationships, and complete the work.  And while you can do it on your time, if you don’t, you will fail and be back working for a boss again in no time.

That means that you do need to put some structure in place to help you.  Not only will it allow you to get more work done, but it will also help your family distinguish between work and play time.  Suddenly, this self-employment thing is starting to feel more like a regular job after all.

Figuring Out What Matters to You

The key is figuring out what matters to you.  What aspects of your current job do you dislike, and what aspects do you love?

What’s not to say that your current job isn’t a lot of fun?  A “real” job can be hugely rewarding and entertaining.  It can also be mind-numbing and skull crushing.

When moving to self-employment, the goal is to find the balance – how can you make money, support yourself and your family, and still have fun.

Maybe you learn from your current employer, see what works and what doesn’t, and apply that to your business.  If you’re changing careers altogether, maybe the journey is going to be the key factor in deciding what matters and what doesn’t for you.

The fact is that self-employment is naturally more work. You’re suddenly going to be wearing every hat in the office: receptionist, salesman, accountant, tech support, and CEO.  Not only are you driven by your vision, but you have to do all the work to support yourself as a whole.

By figuring out what matters and finding a balance, self-employment can be fun, even though it is work.  But don’t forget that the same can be true about work itself.  There is no need to make a jump to self-employment unless that is your true calling.

What are your thoughts?  Do you need to be self-employed to have fun and be happy at work?

Crystal’s Comments:  I don’t think self employment means that you will automatically be happy.  It really depends on the person.  It makes me happy because I’m a stubborn redhead that hates being bossed around and wasting time…that was like the definition of my last job, lol.  What makes you happy?

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13 comments to Moving to Self-Employment: More Fun or More Work?

  • I hate meetings. They always seem to start late because we are forced to wait for someone who is rudely late. Some days it is enough to make me want to quit but I have to work to live. I work in health care and I need to be where the clients are. Just start the meeting without the late comer.

    Dream work would be in my pjs drinking tea without having to do my hair or put on makeup.

  • Very interesting considerations, Robert. Great post!

  • Thanks Crystal for hosting my post! Hopefully it will give people some food for thought!

  • I have definitely been thinking about making the switch to self employment. I guess I’m still a little afraid since W is in sales so that would make that both of our jobs wouldn’t be stable. AH! I just can’t decide.

  • I’ve learned so much since going on my own. While not for everyone, everyone should at least try it. Great write up!

  • One of the aspects of teaching is you are CEO of your classroom. As long as you meet state standards, you are the boss of your room. Very entrepreneurial isn’t it?

  • I always thought that would be an issue. I have always worried that self employment would mean less free time. That is why I went into Radiography, we work on our own (the doctors don’t bother us, they only bother the nurses), the pay is decent, and when I go home I never have to think about work. One day I may wish to evolve, LOL, but right now I am content. I respect those who can work for themselves, it does take a lot of work.

  • This is a great point Crystal! I have been self-employed off and on throughout my young adult life, and really love the structure that a “normal” job brings. And yet I find myself drawn to a life is often self-employed. I am trying out the “niche” site challenge you mentioned a while back from Pat Flynn’s site. I’m only 2 days in, so no judging the site yet. haha. And I am probably going to start my own site pretty soon. I liked your book a lot :) Thanks for all the love for your readers. Keep up the good work!

  • As you mention, there are pro’s and con’s to every choice, including the age-old debate about whether self-employment is a worthwhile pursuit. I think the answer is highly depending on the individual: their personality, their priorities, their lifestyle, their goals, and their core competencies.

    One additional drawback to self-employment is that you often spend time alone, working from home. That can be tough for extroverts who enjoy being in the company of others and who like heading into the office to chat and gossip with co-workers.

    That said, as your business grows you’ll meet clients and others as a result of your work. Plus, you can always socialize “outside” of your working hours. — assuming, of course, that you create boundaries for yourself and force yourself to stop working!

  • I think self employment is both: more work and more fun. There’s got to be a reward for that extra work, right?

  • Dona Collins

    I became self employed a few years ago. The stress of not knowing where my income was coming from each month (as I freelance) was difficult, but it was somehow less painful than the stress and aggravation my corporate job was causing me. They’re different *kinds* of stress, and I wouldn’t turn back for anything.

  • Susanna

    You have already known that the market economic system is distinguished by free business — the independent, initiative activity of people directed on receiving profit. Producers seek to make such goods and services which satisfy requirements of large number of consumers. It allows them to receive the best economic results and profit. Continuous changes in the markets, fluctuation in prices make the businessman constantly looks for new ways, which can lead him to success: changes production, technology, the prices, quality of goods according to requirements of an economic situation. If you are sure you can cope with financial questions, if you don’t need sign up for loans no credit check, if you have enough knowledge and financial basis for start, don’t miss your chance to become self-employment.