Secrets the Cubicle Bound Can’t Tell You

Office Skies

Lets get this out of the way: the freelance lifestyle is not paradise. Heck, work is not paradise.

It’s a necessary evil.

But if you are going to do something to make a living, you better have a good reason for doing it. You better enjoy it. At least enjoy it more than other alternatives. Like a good friend of mine once said, “If I’m going to be miserable, I’d rather be working for myself.”

In other words, freelancing is the lesser of two evils. I like that.

10 Secrets the Cubicle Bound Can’t Tell You

For most of my professional career I’ve worked for someone else. I liked the security that a steady job and steady pay check provided. What I didn’t like was the lack of autonomy, creativity and sense of accomplishment.

I wanted to change that, but never knew how or when. Until I quit my job. I guess making the decision to work for yourself is kind of like getting married or having a child. There’s never a perfect time.

You just have to do it. And since I did do it, here’s what it looks like outside the cubicle.

1. You can say no to projects.

Sure you can say no in a corporation, but you’ll likely lose your job. If you are fortunate enough to work for one of those companies who encourage resistance, you are in the minority. Embrace that job and try not to get fired. Granted, if you say no as a freelancer, you’re not going to get paid, so there better be a good reason why you are saying no. See no. 6.

2. You can work to your natural rhythms.

I’m a morning person so I get up early to write and read. In the afternoon I go for a long run. In the evening I tinker with proposals and project ideas. I try to go to bed before ten. Sure, you could do this as a salary employee, but you don’t have the range of freedom that a freelancer has. Plus, you have to commute [unless you work from home, which is not a bad gig] and buy a wardrobe. Ew.

3. You can travel and work.

If what you do depends upon nothing more than a laptop and a connection, then you are free to roam about the country. Or the world. For long stretches of time. This is one of those perks that make me cringe at the alternative [two-week vacation and holidays every year].

4. You can learn self-reliance.

When you’re a one man or woman shop, you get to experience the entire breath of a business–from marketing to accounting to customer service–that’s otherwise hidden from you as a salary employee. Even though you are a specialist [writer, designer, programmer, etc.], you’re not really because you are responsible for a range of activities. One word of caution: don’t let self-reliance go to your head. Remember, hard work is meaningless without humility.

5. You can suffer from anxiety and euphoria two or three times a day.

The security of a salary job allows you a certain freedom from wild dips into self-pity and loathing. But it also prohibits those corresponding spikes of ecstasy. In fact, you’d be surprised what little things get you depressed AND excited over as a freelancer. You seem to see and enjoy the total scope [the physical, emotional, relational and spiritual] of life from this vantage point.

6. You can understand what you are really worth.

As a freelancer you get to experiment with how much money you make. The initial tendency is to charge low so you get the work. But as you gain momentum you can fiddle with your fee structure and discover what people are willing to pay. Don’t be afraid to do this. If someone says no, then ask them what they would be willing to pay. If you don’t like what they say, then say no. [See no. 1.] However, it’s been my experience that when you promise AND deliver majestic amounts of customer service, people are happy to pay a premium.

7. You can grow from competition.

There’s good news and bad news about living and working in a global market. The good news: your pool of leads is NOT limited to your neighborhood. It reaches around the world. The bad: you are not alone. Other freelancers are trying to do the same thing you are doing. If you want to survive, then you need to be better than them. Karate chop.

8. You can suck it up or sink.

In my experience, salary environments promote complacency. No such luck as a freelancer. If you get lazy, you don’t get work. If you don’t work, you don’t get paid. Besides, if you feel sorry for yourself, there’s really not a water cooler [or the people who hang out there] to share your feelings with. You’ve got to get a grip and muscle your way through the madness. Sometimes alone.

9. You will always have bosses.

I’ve worked for a small, agile operation and I’ve worked for a large, cumbersome one. Getting things done in one was easier than the other, namely because the number of bosses exceeded the other. That number didn’t plummet when I quit my job. Listen: freelancing will not soothe your hatred for bosses, because, guess what, the people who hire you are your bosses. And the more work you get, the more bosses. Learn to love them.

10. You may not love this.

I’m not here to tell you that everyone should work for themselves. That’s naive and idealistic. But who should work for themselves? I don’t know, but I think there are a few personality traits that fit this lifestyle better than others. For instance, the qualities that got me in trouble at one job [aggressive, headstrong and inquisitive] are ideal for freelance work. Comfort with uncertainty and ruthless self-discipline are also a must.

Your Turn

Do you work for yourself? What lessons have you learned? If you work for someone and want to work for yourself, what’s stopping you? Have a great job and zero desire to freelance? Share your thoughts, too. I’d love to hear them. Brutal and all.

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  1. says

    Some great truths right here! Being self-employed can be stressful and one hell of a roller coaster, but I wouldn’t trade it in for anything! But like you said, not everyone is meant to work for themselves. I, for one, like the office atmosphere, so I would love to work for someone else, if I could also have the freedom to do my own thing. However, there’s really no company like that…as far as I know.

    Kudos for you, Demian!

    • says

      Hey Morgan,

      I have to admit I loved the office atmosphere, too…being around people…I also liked the politics, which is strange. It helped that people laughed at my jokes. 😉

      Thank you for stopping by!

  2. says

    So true: customers are boss!

    For certain character types, working for yourself is both liberating and exhilarating. It’s also the scariest journey you could possibly embark upon.

    It’s a great way to learn about yourself, who you are and who you thought you were. It’s a great way to learn about other people too. Business looks different.

    These are ten great points. The point (5) about experiencing life on a different chart is absolutely true. For those feeling ‘lifeless’ and considering such a venture – it will certainly bring you (in) to life as you navigate the highs and lows.

    Being able to work my natural rhythms and travel (anywhere) whilst working are the greatest personal rewards, beyond any compensation package, I have found.

    • says

      Excellent comment. Speaking of compensation packages, that’s one of those things that you have to fight to let go…those packages have quite a pull. Lots of security wrapped up in benefits. 😉

  3. says

    There are many aspects of having a corporate job that I truly enjoy! Working with others, dressing nicely and leaving the house every day, access to training and technology, company celebrations are just a few of the things I enjoy about traditional employment. And then there are drawbacks, too.

    As I work towards my long term goal of self-employment, I know there will be as many positives and negatives. Some of the positives I look forward to include setting my own schedule, working exactly as many hours as I want and need to each day/week/month/year, and discovering new ways to explore personal and professional development to name a few.

    After many years working for small businesses, I’ve seen many of the challenges and joys of entrepreneurship up close and personal. One of the greatest challenges I’ve seen is keeping up with changes in business and technology. A business model that is successful in today’s market may be obsolete in a few short years. Entrepreneurs need to be innovative, flexible and connected. I’m preparing myself to be ready for these challenges.

    Thanks for the insightful article!


  4. says

    Hi Demian,

    I just discovered your blog this morning, and this was the second post I read. I work for myself and I can attest to many of the points on your list. The self-employment journey has singularly been the most exhilarating, frustrating, mind-expanding (and did I mention frustrating?) experience of my life – and I wouldn’t change it for anything or anyone. I’ll never work as hard for an employer as I will for myself. Period.

    Self-employment has pushed me so far beyond my preconceived limits, that I could never locate my original comfort zone again – even if I had a search party – and I’m deeply grateful for that.

    I would like to add to one of your points. Point #9: You Will Always Have Bosses – See, I view clients differently. I look at the client-freelancer dynamic as more of a bartering relationship, instead of as a boss-subordinate relationship. Yes, they pay me, but in exchange for a skill that they don’t have (or don’t have time to execute). I’ve had miser clients – you know the kind – the ones that pay the least, but demand/complain the most. Eventually, I ‘fired’ these folks (politely, of course) because I realized that the paltry contribution they made to my bottom line just wasn’t worth the headaches of writing for them.

    As a freelancer, I believe you should routinely evaluate your client roster, and if the situation calls for it, ‘cut the fat’ on occasion. You may have less clients, but you’ll have more quality clients and you’ll be closer to achieving the 80/20 rule (that 80% of your income should come from 20% of your customers).

    You can’t tell your boss to kick rocks when you work for someone else.

    Another benefit of entrepreneurship is that you can give yourself a raise as often as you like – once you’ve already proven your abilities to your clients, of course. This also doubles as a tactic to rid yourself of cheap clients. This is also great if you’re just starting out and initially charge lower rates to land work. Worthy clients are more than willing to pay your adjusted rates – if they’re happy with your work. When you work for an employer, giving yourself a raise just isn’t an option.

    Just my $.02. I’m really glad that I found your blog!