Making the Right Decision

This week’s post deals with an issue for which clients frequently come to me for help: making the “right” decision. Most commonly, the decision in question is either about relationships (“Should I break up, should I commit?”) or career (Should I quit my job; should I go back to school; should I strike out on my own, etc.?).

Right before I left on my recent vacation I saw a revival of “Follies”, the Stephen Sondheim musical written 40 years ago. It holds special memories for me, as I saw it in Boston, while in graduate school, in its pre-Broadway debut, and loved it then……and still do. The title of the show, “Follies”, has a double meaning – referring back to productions from the days of vaudeville (Ziegfeld Follies) as well as to the folly of looking back with regret on decisions we’ve made in the past and trying to create a present that would presumably have flowed from a different decision.

I encountered a startling real-life example of this last week when I met an old high school friend, whom I rarely see, for lunch. I was showing her photos from our high school days and she suddenly saddened and asked “I wish I hadn’t broken up with Paul”. Paul was a guy she dated for a few months in the 11th grade! The sadness was genuine, but after about ten seconds she said “but if I hadn’t I wouldn’t have the two children that I love”. And, after about another ten seconds she said “And I never would have had the chance to explore who I truly am” (she was a popular high school cheerleader and Paul was captain of the football team; she’s now an artist living in Berkeley, CA – quite a shift in personnas).

So many people are paralyzed by the fear that they’ll make the wrong decision. They come into my office with lists of pros and cons (a technique that logically should make decision-making easier but in my experience almost never does, because it’s the relative importance of each pro and con that counts, a calculation that can’t accurately be made). Or they’re so paralyzed and so sick of the paralysis that they profess to being open to being instructed by me as to what the right decision would be (I always turn down that request).

Look back on important decisions you’ve made, and ask yourself how many of them you can confidently say were wrong. The truth is that it’s virtually impossible to ever know whether a different decision would have led to a “better” outcome. Should you have married someone else? True, you wouldn’t be having the marital problems you’re having now, but isn’t it possible that a different partner would have created even bigger ones? Should you have stayed with the agency you’d been with for 12 years rather than switching jobs only to wind up being “downsized” six months later and now out of work? That depends on what comes next. Should you have moved out of the city to the suburbs? Should you have vacationed in Paris rather than Hawaii? Even what would seem to be a very black-and-white, clear-cut decision (should you have made that investment that went south?) might have ramifications far different from what you might expect; e.g. perhaps having made the bad investment you were forced to sell your condo, which led to your moving, which led to your meeting someone in your apartment building with whom you fell in love, or who gave you a job lead that now allows you to do work you love.

Trusting Your Gut

One essential component of the dilemma many face in making decisions is fear. Study after study has demonstrated that we are biased towards protecting ourselves from the negative rather than objectively and rationally calculating the advantages and disadvantages of a decision. That’s because evolution has predisposed us to be risk averse (an overly cautious, fearful individual was more likely to survive and pass on his / her genes than a bolder person who might occasionally “hit the jackpot”). If you find yourself stuck for some time between two options, ask yourself “which of these would I choose if my fear level were half of what it currently is?”. There’s an excellent chance that your gut will give you the “right” answer. Particularly since there’s almost never such a thing as the “wrong” answer.

To quote the lyrics of a song from Follies, sung by a man looking back on the regrets he has about the marital and career decisions he made decades earlier: “The door you didn’t try, where could it have led? Chances that you miss, ignore. The choices that you make aren’t all that grim”.

If you’re exploring a career change, here’s Jim’s 4-stage process

01

Develop Your Profile

Jim helps you build a concise narrative capturing everything relevant: who you are, what drives you, and where you want to go.

  • Professional history, key experiences, defining traits
  • Core strengths and preferred work environments
  • Salary range, location, company size, and your real decision criteria
  • Your values
02

Identify Promising Options

Jim identifies paths with clarity including responsibilities, entry points, challenges, and genuine trade-offs.

  • Compensation outlook and growth trajectory
  • Transition pathways and entry requirements
  • Key advantages and honest trade-offs of each path
03

Evaluate and Prioritize

Jim assesses each path against your strengths and constraints. A prioritized shortlist formed based on logic and AI feedback.

  • Alignment with strengths, interests, and real constraints
  • Comparison across fit, feasibility, and long-term upside
  • A focused finalist list for real-world validation
  • Conversations with people doing the actual work being considered
  • Research and AI provide validation of choices
04

Getting the Job

Jim ensures that your networking outreach, resume, LinkedIn profile, elevator speech, and interview performance are superior.

  • Network outreach and targeted introductions
  • Independent research and industry trend analysis
  • Informational conversations with people in those roles
01
Jim helps you build a concise narrative capturing everything relevant: who you are, what drives you, and where you want to go.

Client Reviews

Working with Jim was a refreshing and positive experience. As a first-timer to working with a coach, I wasn’t sure what to expect. Jim was spot-on in identifying the primary goals and we achieved them within the four weeks he had predicted. His great demeanor made the process effective and easy. Jim is truly delighted in the progress his clients make. This became clear when seeing the broad smile and satisfaction on his face when he realized we achieved our stated goals and that I had the tools to take the next step in my professional and personal success. He’s a great resource to have.

Michael Veronis

I am so incredibly grateful for Jim’s guidance during a challenging career change. His insight, feedback, and support were essential to my success in landing a dream job. From helping me chart a new course and finding a new passion after burning out in a draining career, to coaching me through final interviews, he was with me every step of the way. I cannot recommend him enough!

Caitlin Lochridge

As an executive search/headhunter I have been lucky enough to partner with Jim on a number of occasions. I have referred several local and remote (Skype, etc.) mid-level to executive-level candidates to him who have reported back to me with rave reviews. Jim has also consulted with me whenever my executive search expertise has been a helpful element to his full-service thoughtful career advice he provides his clients. 100% class act and worth the investment.

Andrew Zalman

Ready to Begin?

The first step is a complimentary 15–20 minute conversation — completely free, no obligation. Fill out the form and Jim will be in touch personally. No pressure, no scripts, just a genuine exchange about what you need.

Phone

(202) 667-0665

Email

Jim@DCLifeCounseling.com

Main Office · Alexandria, VA

2405 Brentwood Place

Alexandria, VA 22306

Part-Time Office · Washington DC

1633 Q St., NW, Suite 200

Washington D.C. 20009

Jim Weinstein
Privacy Overview

This website uses cookies so that we can provide you with the best user experience possible. Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful.