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Career Transition Coaching: 12 Tips for Success

How to Make a Successful Career Change: Career Transition Coaching

Almost all of us contemplate whether to make a career change at some point in our professional lives, some of us more than once. It’s probably easier – and more socially acceptable – than it ever has been to do so, but making a successful career change requires thought and work.

There are a variety of reasons that lead people to contemplate a career transition. While each of us will have our own rationale, Joblist’s Midlife Career Crisis Survey indicates that the top five reasons are:

  • Better Pay: 47%
  • [Current Job] Too Stressful: 39%
  • Better Work-Life Balance: 37%
  • Wanted a New Challenge/ Work Experience: 25%
  • No Longer Passionate About Field of Interest: 23%

You might also consider a career change as your values or career goals change, after getting laid off, or when your family situation changes, such as might be driven by illness, an aging parent, or a relocation.

Many of the recent articles written on career change make the process seem liberating. You get to free yourself from the shackles of your current situation, you get to leave it all behind, you get to rediscover yourself, etc.

But the truth is that successfully making a career change is more difficult than that. It can be daunting, confusing, and stressful. As career transition coach and “Career Relaunch” podcast host Joseph Liu describes his own situation in an article for Forbes,

“Make no mistake, career pivots involve more friction, disruption, and risk than simply staying on a more linear, traditional career path. Having experienced the emotional ups and downs of navigating career changes myself during the past two decades of my professional life, I’m now focused on understanding what it takes to successfully reinvent yourself.”

Wondering how to make a successful career change? With this context, and with the words of poet Mary Oliver in mind – “What is it you plan to do with your one wild and precious life?” – we lay out 12 steps to a successful career change:

Figure out the why

Take a critical eye.

Before you make the leap, consider your reasons for wanting to make a career change:

  • What is it that you like and don’t like about your current role, employer, industry, or career path?
  • How does your current path align (or not) with your values, skills, and interests?
  • From what activities in your broader life do you draw energy? What does that suggest about possible career directions?
  • Why do you believe a career change will improve your sense of satisfaction, purpose or fulfillment?
  • What are the risks or downsides in making a career change?

Be structured and diligent about this evaluation. As helpful, keep a journal or talk over your thoughts with family and friends.

Assess yourself.

If you need some prompts for how to consider you overall career health or the fit of your current situation, check out one of our free career assessments. You can also take a more holistic look, covering your values, interests, strengths, and personality type.

Some assessments that cover these areas are free, but the more research-based ones typically carry a modest fee of $20-50. Note as well that some (such as Myers-Briggs) must be delivered by a certified practitioner, which may add a further cost.

Get outside help.

If ever there is a time to hire a career coach, it’s when you’re considering a career change. Many coaches focus just on this topic.

They can offer a wealth of advice and “war stories” from having seen their other clients go through similar journeys. They will help you sharpen your thinking and avoid the common pitfalls. In this light, they are well worth the investment.


Figure out the what

Discover your inner Ikigai.

You’ll hear many people say, “Pursue your passion, and the rest will follow.” It’s not that simple, and there is even some research offered by author and professor Cal Newport to suggest that people who merely follow their passion are actually less satisfied in the end.

A better mental model comes from the Japanese concept of Ikigai, which roughly translates into “reason for being” and asks you to consider four questions:

  • What you’re good at
  • What you love
  • What the world needs
  • What you can be paid for

Ikigai forces you to blend together your passion, mission, vocation, and profession into your overall reason for being.

Be an explorer.

In his article for Forbes, Joseph Liu talks about conducting a period of “open exploration without expectations.” Suspend judgment and give non-traditional ideas consideration. You can also consider more creative ways to learn about your potential career options through a job shadow or part-time role before jumping into full time work.

One former colleague was considering a shift into venture capital and took two weeks’ vacation to work for a firm that was willing to give her a shadowing opportunity. She quickly discovered that she wasn’t going to like venture capital and went in a different direction instead. By doing the job shadow (albeit at the expense of her vacation time), she was able to avoid going down a path that wasn’t going to be right for her. 

Write your future.

As you’re working to figure out the what, one helpful thought exercise is to write your future autobiography. Picture yourself in the later years of your life. How would you want to describe your professional life and accomplishments to your children, grandchildren, or broader world?


Figure out the how

Do your homework.

Once you have a sense of the change you want to make, dig in and do your research. Accept that no shortcuts exist and commit to a steady march, not a rush.

In Episode 5 of our “Career Sessions, Career Lessons” podcast (available March 7), Chicago restaurateur Rohini Dey discusses her own shift from a career in management consulting into the restaurant business. Along the way, she spoke to dozens of people in the restaurant business and even shadowed a restaurateur to really understand what it would take to be successful. Those conversations helped prepare her for what was a fairly radical change in career direction.

Form a plan…and have a back-up.

Making a career change is a goal. Treat it like any other goal, with specific objectives, interim milestones, timelines, and execution specifics.

Assess the risks and the assumptions you’re making. Be clear on what it means for you and for those around you. Then build in regular steps, akin to the sort of incremental improvement that James Clear discusses in Atomic Habits.

In addition to your primary plan, have a back-up plan. This is particularly important if you’re embarking on a risker path and expect a period of financial uncertainty. It’s always good to have a contingency plan in your back pocket.

Rebrand yourself, if necessary.

If you’re contemplating a significant change, you’re likely going to need to re-position yourself. Evaluate if your existing strengths and experience will be transferable skills relevant in your new chosen direction.

Conduct this exercise on your own, and seek input from others who know you as well. They may see a side of you (good or bad) that you don’t see in yourself, and having that knowledge can only help you as you consider how to evolve your professional brand. Once you’ve identified the changes you need to make, apply them consistently, such as in your social media profiles and your CV/resume and cover letters.


Move into execution

Expand your network.

If you’re making a more significant career change, your existing network is going to be less likely to be able to help you, since it will be a product of your career experience to date.

With that in mind, be deliberate about expanding your network. Find the friends of friends and the experienced pros who are willing to make time for you. If approached in the right fashion, most people will do so. When you meet with them, ask them who else they would suggest you meet and if they’d be willing to make an introduction.

You can also expand your network by joining a professional association (or even an informal MeetUp-type group) in your chosen new space. Jump into some relevant online communities, or attend a conference. Many prior conferences also post videos that are available online.

Plug your gaps.

In all likelihood, you are going to bring a partial set of necessary skills to the new path. Take stock of the skill set you’re going to need and what you have. Address the gaps, through formal educational programs or via the many instructional videos or online courses that are available to you. Job shadows, internships, or contract roles can also help in this regard.

Keep moving.

Set out regular micro-steps, even imperfect ones. Be willing to accept small mistakes as learning opportunities. Track your progress and what you’re learning as you go. Iterate and adapt, and bring yourself closer to the end goal with each adaptation.


While making a career change takes care, thought, and real work, the good news is that most people come through the process better off, as evidenced in the Joblist survey data, where people reported being:

  • Happier: 77%
  • More satisfied: 75%
  • More fulfilled: 69%
  • Less stressed: 65%

In addition, the career changers were making modestly more money, about $11,000 annually compared with their previous positions.

Best of luck to you as you embark on an exciting new path!


Sources and suggested further reading:


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