Choose Your Career Steps Confidently

“Sometimes you have to write to figure it out.” ~Dan Pink, author of To Sell is Human, quoting his former professor in a 2014 graduation address at Northwestern University.


In the same graduation speech, Dan continued to advocate for discovery and exploration by encouraging graduating seniors to do “less planning and more living,” while admitting that such a path is risky. Indeed! He also stated that “The greater risk is to choose false certainty over genuine ambiguity.”

Choosing “false certainty” when you select a college major or choose a career path after graduation is extraordinarily easy because oftentimes you don’t even realize that you’re making that choice.

As you make your first or mid-career decisions, your mind may be clouded by familial pressures and expectations, a strong desire for safety and security, or superficial and glamorous images or perceptions of a certain job. An excessive influence of factors like these can result in a lot of folks still trying to figure out “what they want to be when they grow” or can result in what I’d now call “false work certainty syndrome” (i.e., professional foreclosure). As a professional in recovery from false work certainty syndrome, I recognize the significance of being able to embrace and experience genuine ambiguity.


The ability to choose “genuine ambiguity” in a confident way requires that you are somewhat clear about who you are as a person and what you hope to accomplish and contribute to the world. Completing, reflecting on, and integrating the results of assessments like Gallup’s Clifton StrengthsFinder® is one of the many methods I used to get to know who I am, how I am, and what I value as a StrengthFinder 2.0 bookcoverperson and a professional.

However, taking personality and career assessments have not always yielded the most exciting results in my mind. For example, my top five assessed StrengthsFinder themes were not as dynamic as I would have liked them to be. Having dominant strengths like woo,” “futuristic,” and “maximizer seemed more active and engaging.

So, I paid for the complete test that ranks all 34 strengths in an attempt to see if the strengths I found more attractive ranked just behind my top five strengths of achiever, learner, intellection, input, and connectedness.

The outcome? None of those three “more desirable” themes were even in my top 10! Because of this career-related personal exploration, a new level of self-acceptance and appreciation for how I am was born. My top strength themes accurately reflect the fact that I do love to produce great work, to learn, and to share information and skills.Of course, learning the outcome of a personality test isn’t enough to build the confidence needed to recognize and choose genuine ambiguity.

I believe that many first generation professionals, like myself, need to spend time getting clear about their talents and interests and exploring the possibilities for the best work fit through the following top five activities:

1) Talking with family and friends about specific talents and interests that they have observed in you

2) Conducting informational interviews with professionals in field(s) of interest to develop a more grounded understanding of the everyday work and the type of personalities and cultural norms that exist

3) Completing career and life assessments like the StrengthsFinder and free assessments like iPersonic or SimilarMinds

4) Volunteering or interning at different organization to apply skills and discover new skills and interests

5) Working with a career counselor or coach

I’ll admit that taking these steps requires some effort, but you’ll uncover a lot of vital information that you can use to live a more authentic and enjoyable work life.


Man tearing risk sign
Certainty isn’t always riskier or false. Until the possibility of genuine ambiguity presents itself after getting clear on what you want for the next steps in your life and career, it might make sense to choose certainty.

Recently, I relocated back to the Washington, DC area where I began my working life after graduating from college. Before this transition, I delivered and contributed to work and projects that I proudly associate myself, while working with great people, having a fantastic mentor in the form of my supervisor, and receiving a regular paycheck for several years.

Also, after reading almost every book written by Dan Pink, I got the opportunity to meet him at the World Innovation Forum in New York City last summer. This opportunity materialized, like many others, through chance and fortune. The vice president of my division could not attend the conference and choose to send me instead, due to contributions I made to facilitating innovation within the company.

Making the choice to move back to the Washington, DC area required that I resign from a full-time position and vacate the best apartment that I’ve ever had. Why take this particular leap? Why bring a whole lot of ambiguity back into my life? Because the ambiguity is genuine. This decision is a reflection of my commitment to live closer to the people I love and who know and love me and to connect with work that allows me to maximize the contribution of my strengths and interests (e.g., learning, technology, service, etc.).

I hope that you develop the confidence and have the support to choose genuine ambiguity or consciously live with certainty at whatever phase you are in life!

Here’s that graduation speech…

2 thoughts on “Choose Your Career Steps Confidently

  1. Robert Casillas says:

    Hi, Latoya,

    Glad to see you’re writing on this blog again. I’m a fan of exploring constructs around career, and your articles mirror my experience and challenge me to create a work environment that fits me better.



  2. Latoya J. Williams says:

    Hi Rob!

    I appreciate you reading and knowing that you are a fellow explorer in this process of creating a work life that better reflects your values and interests. While I was in my most recent “certainty” phase, my mind was preoccupied by other areas. However, I did think of the work and community that was started through this blog regularly.

    I’m working to have my next phase of certainty involve themes of career and professional development, so that I can continue to develop and share perspectives and useful insights in this area. I’m also looking forward to experiencing a positive outcome in the next phase of my work life after working through this genuine ambiguity phase again!

Leave a Reply

Your email address will not be published. Required fields are marked *