Updated on 12.31.07

What Color Is Your Parachute? Killing the Doubts

Trent Hamm

parachuteThis is the fourth part of The Simple Dollar Book Club reading of What Color Is Your Parachute?, a seminal guide to your career. These entries appear weekly, each Monday afternoon, and you’re invited to read along. This entry covers chapters ten, eleven, and twelve in the 2008 edition (earlier editions are roughly similar). If you didn’t participate from the start, feel free to jump back to the first part, the second part, or the third part.

Chapter 10: How to Start Your Own Business

This is a pretty basic primer on things to think about before you start a small business. The biggest one, and the one that presents a road block for many people, is the fact that most small businesses earn less than a full time job elsewhere – it takes a lot of drive to really make it succeed.

Bolles also makes a strong case for having a backup plan. What will you do if the business doesn’t take off and you desperately need personal income? In my mind, this is exactly what temp work is appropriate for. A temporary office job doing things like filing papers is the perfect thing to find if you’re trying to get a small business started but you need short-term income.

Bolles is also a big fan of finding a mentor and consistently tapping that mentor for ideas and help as you try to get things started. It’s sometimes hard to find a mentor – my best tactic has usually been to find someone who is in the same area that I’m trying to get started in, but separate enough that we won’t be competitors (they work in a different specific niche or in a different locale).

Honestly, though, this is the weakest part of the entire book. If you’re interested in starting your own business, you’re much better off jumping into materials specifically about entrepreneurship.

Chapter 11: Entering the World of 50+

Mostly, this is a short paean that no matter how old you are, the best thing you can do is stay active, mentally and physically and spiritually. I can’t agree more with this statement: I actively put money into retirement, not so that I can start sitting in my rocking chair and wait for death to claim me, but so I can spend the later years of my life tackling some new challenges, free of the bondage of a boss and a nine to five day.

Chapter 12: How to Get “Unstuck”

There comes a time in everyone’s life (and maybe more than once) where we find ourselves wondering why we’re stuck. Why can’t we make any forward progress? What’s stopping us from moving forward?

Bolles argues that this usually happens when we begin to realize that some sort of change is needed in our life, but we’re afraid to make that change. Quite often, if we’re making that realization, it’s a sure sign that we really do need to make the change, but we’re held into place by the parts of ourselves that resist change – the “safekeeping” parts of ourselves.

One sure sign of your “safekeeping” self is that you’re listing lots of reasions why you shouldn’t do something, even though when you concentrate on it, there are many positive and compelling reasons for doing it. To an extent, I find myself doing this whenever I look at a writing career.

The solutions? Realize that you’re doing it, start doing research on the changes that are needed, and listen to music, particularly classical music (for brain activity purposes – seriously). That last one seemed sort of crazy at first, but I thought about it – I tend to be creative when I’m listening to music, but I tend to do repetitive, ordered tasks much better when I’m not. There is a connection there.

Next week, we’re going to dig into the thirteenth chapter and do the infamous flower exercise. This appears on pages 239 to 250 in the 2008 edition – yes, only twelve pages in a week. That’s because the flower exercise is pretty intense – I plan to work through it next week, and I hope you’ll give it a shot, too.

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  1. KellyKelly says:

    Ack. The “getting unstuck” thing.

    I am so, so, so, stuck. I close the year in just about the same pitiful financial position in which I started it.

    But the “emotional net worth” is further in the red because financial stagnation = regression.

    I truly do not know what change I need to make in order to fix my earning problem. OK, I know on a superficial level — make more money. But why? Why and I stuck at this level? Do I enjoy the anxiety, the shame, and resenting people in my life who have no debt (one of my best friends paid off her mortgage before age 40).


    I appreciate this blog, Trent.

  2. Kris says:

    A lot of people in debt think they have an earning problem – but really its a spending problem.

    Before trying to earn more money, first get spending under control. Otherwise, if you are like most, you will spend the new earnings and be in the same place forever.

  3. sp says:

    The tip about classical music (you mean chamber music in general, right?) is a good one. I have heard that baroque music is particularly good for what you are suggesting. You can’t go wrong with Bach or Vivaldi. Some of the later music — from the classical and romantic periods — is rather dynamic and can be very distracting.

  4. plonkee says:

    You have to really want to change, and even then it’s difficult. On the other hand, sometimes things unstick themselves. Bear with it, do the things that you know are right and see what happens.

  5. KellyKelly says:


    Thank you for that feedback about getting the spending under control. I do appreciate it — that’s why I post my garbage here.

    My spending is very under control. In fact, I should probably loosen up and SPEND some money, such as getting a plumber in here to fix the sink so I can quit drinking from the bathtub.

    I used to be totally debt-free. Paid off my student loan early. Paid cash for (used, carefully researched) cars. Got promotions and raises, stayed in the same small apartment. Had a huge emergency fund. Was generous to people with my time AND my money. On and on it goes.

    I know how that feels, and I want it back. I decided a few years ago to leave my corporate job and start a business. I do not regret that decision, but I do regret some of the bad clients I took a few years ago. Which eventually led to being in what feels to me like a Hindenberg of debt. That is a very quick summary of how I ended up here, today.

    I make a monthly budget. I know where my money goes. I don’t buy gadgets or books or clothes or go to movies or drink alcohol or take vacations. I live like a monk!

    Somebody very close to me, who makes roughly what I do, said recently, “I don’t understand something — you don’t buy ANYthing. I mean, you don’t spend money.”

    She’s right. The difference is, I’m paying on debt and she is not.

    Well, that’s enough whining from me. In my case, it is NOT overspending. I need to get 5 great clients and 5 good ones, unlike my current mix of 1 fantastic client and 8 good ones.

    Stress, stress, stress. Which pollutes the will.

  6. guinness416 says:

    Ambient music has always worked for me; got me through a whole bunch of studying for college & professional exams. Can’t beat a bit of Orbital!

  7. Minimum Wage says:

    Does Bolles say anything about changing “careers” when you are over 50 and all you’ve had is dead-end menial jobs, without any sort of “career-related” experience?

  8. Adjunct says:

    As someone who is 50+ I completely agree with the idea of not just sitting still and waiting for the Grim Reaper to show up. When Katrina blew me out of my home in New Orleans three years ago, I lost all of my adjunct teaching jobs at the local universities and colleges. I really was ready to give up, but I discovered the world of distance education and made myself apply for more than one online faculty position. I was completely stunned when I was hired to teach 5 online classes for several schools! Believe me, my life has been changing for the better every since and my attitude about teaching is brighter than it was when I first graduated college. I am one fellow who can testify to the power of exploring every option in order to keeping moving in the right direction. Also, the money is great, and I can travel when I want to and still make a very healthy living. My laptop is my best friend! I say it is worth every once of effort to continuing discovering one’s hidden assets. I realize online teaching isn’t everyone’s cup of tea, but it has worked out very well for me, and it was a complete surprise.

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