How To Create a Frustration-Free Career Transition –

Career Coaching


When it’s time for a career transition, you know. The day arrives when you just can’t do brand management anymore and you need to become a social worker. Or when you know it is time to move out of that “just for now” job into a “real” career job. Trust yourself when this time comes. 

Women tend to put their own needs behind the needs of their families and the others that rely on them. But making yourself happy professionally is just like anything else – put on your own oxygen mask first, and the others around you will thrive. When you arrive at this point, don’t stress! You can do this, and it doesn’t have to be awful.

Set A Reasonable Timeframe for your Transition

First, set a reasonable timeline with fair expectations of yourself.  You don’t have to make the change overnight. Set a timeline to reach your goal. Six months? Over a year? Be sure to factor in any education you may need. A good rule of thumb is that a job search will average about four months, so add time on to that depending on how far afield you are going in your transition.

Avoid the trap of thinking you need to make the transition quickly. I see both men and women begin to immediately network 24×7 as soon as they have made up their minds. This can lead you to become discouraged and burned out before you have given yourself a real chance at change. Being thoughtful and systematic is your best chance at success. 

Set Some High-Level Milestones for Your Transition Plan

Next, set some high-level “starter” milestones. Do you need a certification program? Do you know what to otherwise do to achieve your goal? Some examples of milestones could be:

  • Talk to people in the field about how my skills will translate
  • Identify the best books, blogs, podcasts and thought leaders to follow– gain an understanding of current trends, ideas, and changes in the field I am targeting so I can speak intelligently about it
  • Network to find the best level, roles, and organizations to target
  • Develop a database of contacts who can help me once I begin in earnest
  • Develop the additional tools I’ll need to start a job search: elevator pitch, resume, cover letter

Add more milestones, and timeframes, as you continue you planning and zero in on your target achievement.

Give Yourself Permission to Make Time for Transition Planning 

Once you give yourself a timeframe around your goal, and give yourself permission to make it a priority, you will be surprised at how much better you feel immediately.

As women, we tend to put our own long-term goals behind everyone else’s daily goals. Be realistic about balancing commitments in your life but make your transition a priority. Don’t take time away from yourself, find time to give just a little less somewhere else. Don’t skip yoga or some other type of workout or exercise class.

Set Weekly Goals to Achieve Some Progress Each Week

Weekly goals are one idea that allow you to be flexible with yourself but still move forward. If you know this week you are going to be way too busy to do much about moving towards your future life, do one thing on your transition plan. During a week when you know you will have more time available, plan to spend a lot more time. Meeting weekly goals can give you a great sense of forward momentum.

Learn The Glossary for Your New Field

This seems like an oddball recommendation, but it will make a world of difference. Every industry has its own set of terms, short-hand, rules, and insider knowledge. Learn to speak the language with colleagues so that they start thinking of you like one. When I was working in the early 2010’s with clients getting out of financial services, they were amazed at how easy it was to transition from selling retirement products to selling SaaS (software as a service). What made it frustration free? They already knew how to sell, but they needed to learn how to talk about selling software. For your own transition, learn to talk about the value you can add in a way that will make people listen.  

This is especially important for women, as we tend to downplay our own strengths and abilities. Using the language of your interviewer or the person you are networking with goes a long way towards earning you instant credibility that will improve your real time confidence.

Have A Quantitative and Qualitative Idea of What You Are Looking For

Moving into the role that is going to light you up is one thing, but you don’t want any surprises like finding out too late you will need to give up your daily fancy coffee or paid dental.  Make one of your steps a detailed inventory of what you are looking for in a change quantitatively and qualitatively. Then flip things to the other side and start thinking about what you would not give up. Be able to answer the questions that are meaningful to you. For example,

  • Are you willing to move?
  • Are you willing to work in a different area?
  • Will a WFH or hybrid situation be important to you?
  • What pay decrease could you accept?  What pay increase would be your goal?
  • How much vacation time will you need? Heath care? Other benefits?
  • Is a small or large office important?
  • Are there situations that would impact your childcare?  Can you accept those situations?

If the only goal that matters to you is making this transition, that’s great! Just know in advance that everything you have now is not a given for what you might get.  

I’ve made a couple of difficult transitions successfully and similarly helped numerous women seeking more pay, fewer hours, and more rewarding work. They’ve told me these steps are the ones that really made the difference. You got this.

This guest post was authored by Amy Feind Reeves

Amy is the Founder and CEO of JobCoachAmy, where she leverages her 25+ years of experience as an executive and hiring manager to help professionals at all levels of their careers find and keep jobs that make them happy. Her corporate consulting practice focuses on career coaching for Millennials and Generation Z, as well as consulting on practical approaches to implementing improved management practices. 

As a sought-after expert, speaker, and career coach, Amy works globally with clients across a wide variety of industries including finance, consulting, media, consumer products, technology, and healthcare. Her functional expertise–gained from nearly two decades of working with companies and organizations to reduce costs, increase revenue, and improve processes–is significant across all areas of business operations.She has been featured in countless media including the Wall

Currently, Amy supports the Anaya Tipnis Foundation in scaling its operations nationwide and developing its career services workshops. The Foundation offers scholarships, mentoring, and support to first-generation college students as well as provides internship and networking opportunities. 

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