Overwhelmed with possibilities when plotting your career? Try this approach

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Having a gigantic selection of career possibilities is a good thing, right?

Not so much if you have a huge desire to make a change in your life and feel overwhelmed by choices.

It reminds me of my single days, when I didn’t have my handsome, warm husband at home.  In any social situation, there would always be that nagging question in the back of my mind:  Will “he” come swaggering in the door today?  Could this guy be “The One?”  How will I know?  What if he is not and I miss out on “The Real One?”

In that kind of context, possibilities are kind of exhausting.

What should you do?

The same is true for people who feel paralyzed trying to figure out the next step in their career.

  • Should you quit your job, make a dramatic exit a la Jerry Maguire, read your manifesto to the entire office, take your fish and figure out next steps later?
  • Should you start a small business on the side?
  • Should you sign up for the MLM business your brother-in-law has been pestering you about for the last eight months?
  • Should you look for another job to tide you over until you figure out what you really want to do?
  • Should you move back in with Mom and Dad?

All of these questions leave you stumped if you don’t have any context or criteria for your decisions.

In fact, in the middle of writing this post, I got this email from a new newsletter subscriber (referenced with her permission):

“I am pondering self-employment. However, I’m not sure that I would’ve given it a thought if it had not been for an unceremonious parting of the ways with my previous company. After a year of struggling with a new manager, we both realized that I was leading a program in a different direction than the direction she wanted it to go. I was given a couple of unpalatable options so after 8 years of contribution I moved on.

Only I don’t have another job. And I need one. But I don’t ever want to get stuck again in such a bad situation. So I’ve been exploring consultancy or freelance work. However, that takes a lot of effort and energy that is different from the effort and energy that goes into finding a new job. How can I tell which direction is right for me? Are the 2 directions mutually exclusive? If I’m serious about self-employment should I take a bridge job to tide me over until self-employment can be made a reality?”

Define your ideal life

What I suggest to this kind reader is to spend some time fleshing out a picture of her ideal life, which doesn’t have to include a specific description of an ideal job, or an ideal business just yet.

It can be something like:

  • I live in Boston
  • I work about 20 hours a week from home, doing a variety of freelance projects.
  • Virtually all of my business is conducted over the internet.
  • I travel to deliver keynote presentations six times a year in major cities like London, New York, Chicago, San Francisco, Tokyo and Hong Kong.
  • I have a small team of great partners who compliment my skill set. We all work for ourselves.
  • I have a happy and fulfilling home life.  I am present in my kids’ lives and have time to participate in school activities, help with homework and bandage skinned knees.
  • I exercise every day.
  • I have “x” dollars in retirement accounts and “y” dollars in savings.
  • I make “z” dollars per year
  • In my spare time I am a backup dancer for Beyoncé

Once you begin to develop this big picture of your ideal life, you can create a list of “must-do’s” to accomplish that picture.

The must-do list

This list can contain things like:

  • Skills to learn (writing, freelance marketing, sales, accounting, Hip Hop dancing)
  • Experience to gain (teaching, blogging, creating websites, presenting)
  • Money to accumulate (retirement cushion, launch fund $, savings accounts)
  • People to connect with (mentors, partners, friends, Beyoncé)
  • Places (to live in, visit, frequent)
  • Brand to build (incoming blog links, press mentions, raving fans)

Then, with this list in mind, you can select your next step with the specific purpose of checking off a few things from your list.

  • You could choose to take a job in Boston which would get you settled in the place you intend to live
  • You could take a less than ideal, but very short-lived and high-paying freelance gig that would allow you to bank up the money needed to start up your business
  • You could move back with Mom and Dad with no shame, in order to have time to get your freelance business off the ground without the pressure of paying for rent
  • You could start to perform your backup dancer skills at Talent Night every Friday evening in every surrounding city

What if your ideal vision changes?

Of course your ideal life vision may change as you start to make concrete progress towards it.  Most likely, you will make a series of tweaks as you get experience and information about what will make you the most happy, healthy, wealthy and wise.  Expect things to change a bit.  Just pay attention to making concrete progress in gaining the specific skills, experience, knowledge, contacts and resources to bring your dreams to life.

By choosing criteria, you can give yourself a break

We tend to get quite melodramatic when we make career decisions.

  • If I take a real job again, I will show the world I am a failure as an entrepreneur
  • Only losers sleep on Mom and Dad’s couch
  • If I take on one less-than ideal project, I will be doomed to do them the rest of my freelance life

This is only the case if you choose to see it this way.

When I was pregnant with Josh, I chose to work on one of those “less-than-ideal-but-megabuck” consulting projects.  The travel schedule was grueling — I traveled every single week from Phoenix to the Bay Area and worked on things that weren’t necessarily my core passion.  Because I get terrible morning sickness when pregnant, the travel was really a pain.

But as a result, I was able to bank up a bunch of cash and took a whole year off after Josh was born.  This allowed me time to change directions in my business, start a blog (this one!) and spend lots of time learning about online branding and marketing.  It was definitely worth the momentary discomfort!

I hope this approach to career planning gives you a bit of context and decision criteria for your next step.

28 Responses to “Overwhelmed with possibilities when plotting your career? Try this approach”

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  4. […] have mentioned this one before, but I think Pam Slim has a lot of great advice. This post on how to plot a career when you are overwhelmed with the choices is […]

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  7. Adarsh says:

    It’s really difficult for us to choose out career path when we have a lot of options.

    Even though I have found my passion, I still get weird thoughts of doing different jobs since I am just 22 and still have time to experiment.

    P.S: The youtube video no longer works

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  14. Dayflyer says:

    Many people seem to think their career decision is in some way commiting them forever, while in reality they’re likely to work in several different career areas, by choice or necessity.

    If a job will help you acquire a skill set you need, or get to a place you want to live or experience, it’s worth considering – but as a piece of the overall jigsaw that makes up your life.

    Stop worrying about whether it’s the right decision, and get on with capturing the positives out of the experience!

  15. topseekrit says:


    I know this is late but men this almost described my ideal life – I would LOVE to be a back up dancer for Beyonce or Janet Jackson, LOL. I dunno about living in Boston though, somewhere close to home but much bigger like Costa Rica or something.

    Anyway, this is a spot-on post. I was very scattered in 2008 with my goals, trying to do too much. Now I’m working on simplifying and getting one step closer to the life I want to live. It certainly isn’t easy!

  16. Sciennetguru says:

    The blog is not bed:)

  17. Mark R says:


    Another great post. As I am moving toward independence, I find that the one think that trips me up is the money.

    I would make the recommendation that you first of all always plan to leave the job you are currently occupying. This allows you to make a habit of saving for the future, whether you create it or it is thrust upon you..

    Secondly, for a day or so live the life you want. Attend events you aspire to be a part of, practice your craft, maybe even change your look or attire. Even participate under an assumed name.

    Be the dream

    Become who you want to be!

    Determine if it is all you think it is, then act upon it.

    POWER ON–Mark


  18. Kristina says:

    Thank you so much for this great post! It helped me to write advice for our community, here: http://biztropolis.ning.com/profiles/blogs/pitfalls-on-the-road-to-career

  19. Pamela Slim says:

    @Emily – so glad it is timely and useful!
    @Kathryn – I hope she feels better about choices, including if she sleeps on your couch 😉
    @Marsha – I think we can really beat ourselves up for taking jobs/gigs that may not meet all our criteria. Done strategically, it can be great move!
    @Andy – flattery will get you everywhere. As for your son, tell him Jay Z is on speed dial, so there will be no prob making intro to backup dancers. 😉
    @Lisa – if it ain’t fun, why do it? 🙂
    @Debbie – thanks! Good to see you here, happy new year!
    @Matthew – I agree, that which you measure tends to get done.
    @Diane – I am so glad it helped. As often happens, when writing a post, I get tons of questions on said topic. Cosmic reinforcement, surely! 🙂


  20. This is a great exercise, Pam. I’m currently in the middle of some huge business and life changes and I’ve been struggling with being overwhelmed by all the options and directions I could go in. This was a great thing to do to help center me a bit. Thanks!

  21. Timely post for those thinking of professional New Years resolutions. The chart example also emphasizes that that which is measured gets done! Hold yourself accountable for taking steps in the direction of your goal.

  22. Debbie Weil says:

    This is brilliant! Thanks

  23. I love your practical ideas, and I plan to put several of them to use. Thanks for infusing fun too.

  24. Andy Pels says:

    It already seems that this will be a big year for people facing such decisions. If they stick with you they stand a great chance of emerging in a much better place.

    Now that I’ve flattered you, will you introduce my older son to a backup dancer for Beyoncé – maybe one from the “Single Ladies” video? I know you know everybody.

  25. Super post – and very practical, Pam. This is going to help many people get going in the right direction in 2009! Love your story about taking the job for money while you were pregnant – then spending a year with Josh as a result. This is the kind of thinking and planning we can all benefit from.

  26. This is a very thoughtful and pragmatic post, Pam. I’ve just forwarded the link to my daughter who is weighing some of these very things. Thank you so much! Very helpful!

  27. Emily says:

    This is great – and perfect timing. I just gave notice at a job I hate and have no idea what I am going to do next. I was needed a place to start and this seems like it will help nudge me out of the paralyzing fear and back into creativity and action. Thank you!