Last time (Part 3) I talked about how to discover your values and gauge the type of money you’ll need to earn for the lifestyle you desire. In this installment of the Career & Money series I want to talk about finding the right fit and the myriad of ways you can earn money.


Now that you’ve discovered your values you should be starting to get a sense of what is Building Blocksimportant to you in terms of your life plan and your career plan. As I’ve shared before it is crucial to have these be in alignment. Otherwise you’re faced with a lifetime of miserable Mondays and the prospect of finding a way to numb the pain of a daily existence that makes you truly unhappy.

When it comes to finding the right fit for your career you need to not only take into account your values but also your preferences. This is where getting to know yourself intimately pays dividends. You learn at the core: who you are, what you want, and what you truly do not want from your days on the planet. This relates to your work life in terms of a number of factors. Consider these aspects of a typical career and ask yourself — if I am to feel alive and thrive in my career, how would I answer the following questions?

  • Do I want to work for someone else or for myself?
  • What type of employer would I like to work for? (For profit, non-profit, academic, government, start-up, etc.)
  • How large or small of a company would I like to work for?
  • Am I a strong, self-directed person or do I like a lot of direction?
  • Do I love to lead or prefer to follow?
  • What type of work culture do I enjoy? (Conservative, cutting edge, open, hip, old school) How do people treat one another and how well do they walk their talk?
  • How supportive is my employer of my sexual orientation? Do they have policies in place? Do they walk their talk?
  • What type of physical environment do I work best in? (Albeit, I’ve yet to find a soul who loves a cubicle, there are many who feel right at home there/)
  • What skills and talents do you want to use in your job? Do you prefer mental or physical work? Like working with your hands or on a computer? Love to interact with people or prefer solitude? Teams or independent projects?
  • What industry might I want to work in? (Retail, electronics, pharmaceuticals, health care, software, etc.)

As you answer these questions keep on writing about what your ideal situation looks like. Tap into the feelings behind why you answer the way you do. How strongly do you feel about your answers? For instance, you might absolutely feel 100% strongly that you want to work with people yet the industry you work in doesn’t matter quite as much. Take note of this so you can dissect your answers to arrive at a list of attributes for the career you most desire. On this list consider having 3 categories:

  • “Must Have’s” = the non-negotiable attributes
  • “Like-to-have’s” = items that you are willing to negotiate or at least have intermittently throughout your career
  • “Neutral” = you really don’t have a preference

As you make this list, do not shortchange, second guess yourself, or start making compromises. I can tell you now that your mind will try to rationalize your heart’s wishes to fit some preconceived belief you have about how things “have to be”. Or, how “reality” works. As someone who has spent much of her adult life feeling like a square peg being hammered into a round hole I can’t emphasize enough how important it is to honor the answers your insides are telling you in this exercise. If you try to fake it you will make your life a living hell. That doesn’t mean you won’t ever work in a less than ideal career (I’m not smoking something funky here when I write these posts), but you need to be conscious of what your real needs, values, and preferences are if you want to have success on your own terms and design a life you love over the long haul. Think I am being overly dramatic?

Consider this recent article by Pam Slim over at Escape From Cubicle Nation called “I have a “great job,” lots of money, responsibility and respect. Why aren’t I happy?” As I read this I almost wondered if Pam were writing about me (as it relates to my corporate job which I am working to transition out of). I remember having the same epiphany – “What a relief! Now I know why my day jobs have never been a fit and it’s not because there’s something wrong with me!” when I was training as an Integrative Coach with Debbie Ford. Pam likens the wrong job to being forced to wear the wrong sized shoes. For instance if you wear a comfy size 8 shoe and then try to spend your life wearing only size 6 ultra-narrow stiff pumps. It’s painful and ugly. She goes on to ask the million dollar question:

So why in the world do we try to jam our foot into an unattractive, uncomfortable shoe, otherwise known as our day job?

Because our social self (shaped by family, educational institutions, the media, religion) is so strong that we believe that our “great job at an investment bank where I have an outstanding reputation, many years experience and an amazing salary” should make us happy. Even if we know that it is in direct contrast to the picture of our ideal life!

Indeed! We try to rationalize our way into a belief that we “should” be happy because, after all, look how wonderful things appear on the outside. To me it is like the futile silly statements we hear as a kid “eat your peas because people in the third world are starving”. Did that statement ever make you feel better about peas? Did it help even a single soul in the third world feel satiated? I don’t think so. The same holds true for careers that you ‘think’ should be a fit but yet feel like hell.

The Ways to Make Money are Endless

We often get fooled into thinking that there is only one way to earn a living. At least for me, having had only role models of people who worked hard for others and traded time for money, it took me until just a few years ago to realize there really are other ways to earn a living. While I won’t fool you, you still need to invest time, expertise, and hard work, it shouldn’t feel like drudgery. Even if you decided back in Part 2 of this series that you didn’t want a career and only wanted a job, you still shouldn’t settle for being unhappy ever day.

If you Google the phrase “ways to make money” you get over 45 Million results. While I bet a lot of them are get rich quick scams, my guess is there are still millions of ways you can earn a living. In fact, so many people now desire to do a variety of careers all at once; the term portfolio career was born. A portfolio career is one in which you work at multiple careers at the same time (all part-time) and they combine to make one full-time career (and revenue stream). Just off the top of my head I can think of the following ways to earn money:

  • Work full-time or part-time for a company
  • Freelance
  • Own your own business
  • Sell products (online or off)
  • Sell services (online or off)
  • Turn a hobby into an income stream
  • Invest your money (real-estate, financial investing, etc.)
  • Creative/artistic pursuits

These are only broad categories. Within these there are tons of different combinations and possibilities. Just think of the sheer number of different types of business you could own (solo, small, multi-level marketing, franchise) and then the possibilities beneath that. It could go on and on. My point being — don’t fool yourself into thinking it has to look a certain way based only on what you’ve seen to date or seen modeled for you by friends or family.

So, get started making that list what type of career you really want. If it doesn’t match up with what you have now, don’t sweat it — awareness is the first step toward changing things for the better. Next time I’ll be talking about how to get that job you really want.


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Paula Gregorowicz is the Comfortable in Your Own Skin(tm) Coach and you can learn more at her website www.thepaulagcompany.com and blog www.coaching4lesbians.com .

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