Who among us hasn’t had to make difficult decisions? Whether it’s leaving one job for another, staying in a relationship or ending it, “tying the knot,” having kids, firing an employee you really like, or even getting a dog or cat, sometimes making a choice can be agonizing.

Decision making is very much on my mind right now.

For 2 years I’ve been toying with the idea of leaving the city and moving to the suburbs. I just had to find the right house.

Then last month I finally did, a house that met my numerous criteria, and I had to “fish or cut bait.” But the prospect of leaving urban life (which is the only life I’ve known since starting my first job in Manhattan decades ago) and moving to the suburbs was unsettling – truly a step into the unknown.

I thought it would be valuable to share with my readers some of the strategies I’ve been using to cope with the discomfort involved in making this difficult decision.

Initially I used quite a bit of visualizing the positive aspects of moving forward. How bright the house was, with its myriad skylights and floor-to-ceiling windows. How nice the garden would look. What it would be like to have neighbors that I actually got to know. Focusing on the positive aspects of change can be important in making decisions about moving from a not-so-bad situation to a potentially better one, because the inertia of the current, not-so-bad situation can be paralyzing. Why risk upsetting the apple cart? That’s what makes it so important to amp up the benefits of the change. Visualizing is a pretty easy way to get there, but actually engaging with the new situation (in my case meeting the neighbors and talking with them about what they love about their community; window shopping for furniture that would look great in the new house) helped make the benefits of the future course of action more real.

An even better way of utilizing this technique is to physically engage with the one method that a lot of people TRY to use, but that inevitable fails, is making a list of pros and cons. This is an exercise that can be valuable as an initial step because it fleshes out the relevant considerations (at least potentially, if the exercise is approached rigorously), but it’s really impossible to accurately weigh the importance of all of these factors, which makes it impossible to total up the pros and cons and see which comes out on top.

If you’re considering taking a job at a new organization, talk to as many people as you can about what they love about their work there, as well as what they might not like. If you’re considering getting a pet you might want to foster first. Harder to do in the case of a decision about marriage or kids, but talking to friends who have experience with these decisions can help.

It’s important to take the appropriate amount of time to make the decision. What’s appropriate? Well, you want to avoid coming to a decision too quickly in an effort to alleviate the anxiety caused by facing the difficult decision. On the flip side you want to avoid endless rumination; notice if you’re plowing the same ground over and over again in your mind – if so you’re not really advancing the process.

Another method is to imagine yourself 10 or 15 or 20 years in the future looking back on the decision you will have made. How do you think you’d feel about your choice? Yet another: imagine the worst case scenario. Could you deal with it? How likely is it to happen? Could you cope if it did?

A final technique I’ve used is to think back on past difficult decisions I’ve made, reminding myself that despite the agony of the process it ultimately worked out for the best. Of course this won’t be a very good technique if you’re someone who has a lot of regrets about past decisions, but I’ve learned that most people have made good decisions most of the time. This will be particularly true if you find yourself excited at times about moving forward, which suggests that there are enough positives to the new situation to enable you to make it work.

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

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(202) 667-0665

Email

Jim@DCLifeCounseling.com

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2405 Brentwood Place

Alexandria, VA 22306

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Washington D.C. 20009

Jim Weinstein
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