One account of the moon landing is that Buzz Aldrin, the Apollo’s pilot, was asked to take the first human step on the moon. He hesitated for only a few seconds and lost his chance. Neil Armstrong had no doubts and is now immortalized in history. [1]

This account probably isn’t true – Armstrong took the first step because of the design of the Eagle lunar module [2] – but, why ruin a good story when it makes my point so well? Fear and hesitation frequently stall us, causing us to miss exciting opportunities. I’ve worked with many clients who know they need a career change but don’t move forward because of uncertainty. Fear of making the wrong decision is a common cause of the uncertainty. If this is your experience, here’s a path forward.

Start by Determining What Has Worked in the Past, and What Hasn’t

Grab your resume. Rank each gig from 1-10 (10 is a job you adored). Make a job description for each gig. Your next move should have a job description similar to any of your jobs that ranked between 8-10. If you’ve had multiple gigs that rank between 8-10, you’re in a good place.

If every gig you’ve ever had is below 7, I suggest a different approach. You’ll want to do some serious self-awareness work. Once you’ve got a one-page self-awareness cheat sheet that describes your three greatest strengths, you’ll want to compare those strengths to the gigs you disliked. Odds are, there will be a big disconnect. We’ll need to change that.

The things that didn’t work often help us determine what will work. A client, who was considering a career as a trial lawyer, learned that he hated conflict. His self-awareness work revealed he was extremely collaborative and agreeable, making him a much better fit for customer service or relationship management.

Find Compelling Possibilities

Once you’re clear on your strengths, it’s time to find places that value those strengths. Create a LinkedIn account and then enter your strengths in the search bar. A charismatic person could search like so:

Charismatic LinkedIn Search

Here are just a few of the more than 8,000 results. Many of these will be job possibilities that you’ll have never heard of and would never learn about if you remained stuck in the mire of indecision.

LinkedIn Search Results For Charismatic

Each of the job descriptions will include the strength you searched for. Many of them will not be a fit but that’s ok. Make a list of the ones that might interest you.

You can add to the list by speaking with your weak connections. In her book about the importance of the twenties, Psychologist Meg Jay urges twentysomethings to emphasize their careers [3]. She argues you’ll be more likely to find new career possibilities by asking for help from people you know, but don’t know all that well (your weak connections). This is because your strong connections already know you well and would have already made suggestions if they had value to offer. Bring your self-awareness cheat sheet to quick coffee meetings with weak connections and ask them if any possibilities come to mind.


Once you’ve got a list of possibilities, don’t just pick one. Experiment, so as to prove to yourself, and the employer, that it’s a good fit. Create as much of a simulation of the work as you can and like a scientist, write a lab report showing your results. This is easier to do for some jobs, than others, but in most cases, you’ll learn a lot.  I wrote an article about career experiments here.

Once you find areas in which your experiments yield poor results, cross them off your list. Keep going until you find possibilities you enjoy. If you’ve found multiple possibilities you enjoy, you’re in good shape! Once you’ve found a gig you enjoy, organize informational and formal interviews to show employers that you’re up to the job. They’ll be impressed by all the work you’ve done since few other job applicants will do that much work.

Of course, there’s much more to say about how to get the gig you want. More from me on that later. For now, please tell us about you. Has your career even been caught in the quicksand of hesitation and fear? And if you’re there, now, what’s your plan to escape? Email us here.

Talk soon!
– Dan King.
Founder & CEO,