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7 Key Emotional Challenges to Overcome When Transitioning Careers

Changing career paths isn’t just about rewriting your resume

Joseph Liu
Career Relaunch
Published in
9 min readNov 21, 2023

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When attempting a career pivot, you might find yourself disproportionately focusing your efforts on the practical aspects of changing careers like reworking your resume, networking with people in your target industry, or brushing up on your interview skills. All these efforts are important.

Equally important is dealing with the emotional aspects of walking away from one career path to pursue another. Your ability to manage and overcome seven challenging emotional dynamics will have a direct impact on your ability to successfully execute your desired career change.

1. Departing From Your Established Career Creates Uncertainty

Almost exactly 10 years ago, I resigned from my global brand marketing job to start my own independent career change consultancy. It marked the end of a decade-long stint marketing products and brands to consumers.

During my initial transition, I went through a period of emotional confusion, unsure whether I’d made the right decision. I felt like I went from having a coveted position at an established food company, marketing a globally recognized brand loved by consumers around the world to suddenly working on my laptop on my kitchen table, pounding the pavement to find clients, and penny-pinching to offset the limited income I initially brought in.

While I had a vision of creating my own thriving, independent business, I honestly didn’t have a clear sense of whether I would succeed. Many clients and audience members I now speak with express a similar level of concern around the risk involved with starting something new, especially if what you already have isn’t too shabby.

“During the career change process, there will be a large amount of uncertainty — especially if the change is between industries or areas of specialism,” according to workplace psychotherapist Eloise Skinner. She recommends accepting ‘the unknown’ as part of the journey, and not striving too soon for certainty.

2. Letting Go Of Your Identity Involves Loss

Departing from a job can almost mimic the feelings of grief you might experience after losing a loved one or breaking up with someone. In many ways, our work can almost feel like any important relationship that requires ongoing effort, communication, and understanding for it to thrive.

When I departed from my corporate role, I felt a tremendous amount of loss, almost as if some part of myself had died. That may sound melodramatic, but until I left my career behind, I never realized how much of my self-worth had been wrapped up in my professional identity as a marketer. Even to this day, 10 years later, I find it difficult not to refer to that part of my career because the experience was so formative.

“A surprising emotion people often confront when voluntarily switching careers is grief,” says Dr. Daniel Boscaljon, director of research and co-founder of the Institute for Trauma Informed Relationships. He reminds though that grief can be useful. “Grieving is a healthy and appropriate emotion that attaches to the loss of an old identity and to the relationships that supported it.”

3. Heading Into The Unknown Is Scary

Regardless of whether you love or hate your job, walking away from any career path involves dealing with several unknowns about what exactly you’ll do next or whether your move will really result in you being happier. I’ve had situations where I knew I needed to make a change but didn’t exactly know what I wanted to do next. In other cases, even when I had a plan in place, I didn’t know how things would transpire.

When changing careers, “the biggest emotion to master will be fear,” according to psychotherapist and accredited member of the British Association for Counselling and Psychotherapy (BACP) Nicola Ball. “Going from the known to the unknown creates uncertainty, which can create anxiety and fear. Our brains are hardwired to protect us, and we mostly feel at peace when we have certainty.”

However, Ball reminds us that staying in your current career may cost you more in the long term. “Feeling the fear and doing it anyway is my best advice. The time will pass regardless of what you do, so why not follow the career path that fills your cup.”

Jeanne Nangle, an emotional well-being coach agrees that changing careers can be very unsettling. “Even a voluntary change can evoke a sense of loss for the familiar. Human beings are drawn to what’s familiar.” She recommends allowing yourself time to appreciate the past, and then turning your attention to the growth potential ahead.

4. Doing Something New Rattles Your Confidence

Working for any well-known brand often results in having no shortage of invitations to fancy events, partnerships, or media opportunities. The week after I left my corporate marketing job, I served as a judge for a big marketing awards industry event in London, something I’d been invited to do before I resigned from my marketing role.

But on this day at the judging session, when everyone introduced themselves, I was suddenly the only person not affiliated with a big-name brand or agency. I remember during the coffee break, everyone was mingling with one another, and literally, not a single person made any attempt to talk to me, which I found very eye-opening.

On the one hand, someone not talking to you because you don’t hold a certain job title or affiliation may seem shallow. However, you also can’t blame people for tending to flock toward professionals they can immediately make sense of. When you shift to a less recognizable job title or affiliation, prepare yourself for a bit of disenfranchisement, which can be hard to stomach.

According to Gena Cox, founder of Feels Human, after departing from a successful career path, professionals may initially struggle to interact with new colleagues, managers, clients, or customers. “They are afraid of failure and fear seeming less relevant than in their previous career. They may not be able to have the immediate impact they had in a more familiar situation. This can lead to feelings of feeling unseen or irrelevant.”

Cox recommends giving yourself time to learn the ropes of your new role, accepting the inevitable discomfort that comes with starting something new, and constantly reminding yourself of the value you still can offer given your unique previous experiences.

5. Giving Anything Up Creates Anxiety

When I left the corporate world behind, it felt like I was giving up a lot. My association with a well-known company. The instant credibility I got from working for a global brand. The reputable title that got me invited to comment on articles, speak at conferences, or be courted by potential suppliers or agencies who wanted to work with our brand.

Those days suddenly disappeared after I departed from that brand. It led me to doubt my own worth and value.

When you invest time doing an advanced degree, energy into climbing the corporate ladder, effort associating yourself with your former company, and time into building certain relationships, walking away can fill you with a sense of loss and discomfort.

“Anxiety often accompanies major career changes due to the fear of the unknown, potential financial instability, and the pressure to perform in a new role,” says therapist Keisha Saunders-Waldron. “Managing anxiety involves understanding and practicing self-compassion and acknowledging that it’s normal to feel anxious during transitions.”

6. Starting Over Shakes Your Self-Esteem

Shortly after I left my last corporate job, I couldn’t help but notice updates on LinkedIn where my former business school classmates or colleagues had been promoted to vice president, marketing director, or even C-Suite roles. I wanted to feel happy for them, but instead, I secretly felt a bit envious of their ascent.

In the early days of starting my business, I found it hard not to wonder where I could have been had I remained on my marketing career path. I never regretted my decision to leave the corporate world per se, but at moments like this, I found myself wondering if and when I would ever reach a similar level of accomplishment in my new career path. I would literally lay awake at night questioning whether I’d departed my marketing path too hastily.

“The act of stepping into the unknown is naturally anxiety-provoking for most people,” according to corporate psychologist Dr. Claire Vowell. “This can sometimes lead to catastrophizing or imagining the worst-case scenarios.”

When beginning a new chapter in your career, you may feel immense pressure to quickly sort things out, to make ends meet, and to prove to yourself and others you’re still a “legitimate” professional. You may find yourself doubting your capabilities or future potential.

Dr. Vowell recommends first taking note of when you fall into negative thought patterns, and then reframing those thoughts to be more balanced. For example, acknowledging that tackling anything new will be challenging and take time, and accepting it as part of the journey.

7. Leaving Investments Behind Generates Guilt

Any career involves investment. The investment of time, effort, training, belief, and education. And these investments can pay off in many ways. Your job, even when you don’t find it completely fulfilling, still provides you with income, community, a professional identity, credibility, and stability. If you’re lucky, it may even afford you a cushy lifestyle, corporate perks, healthcare benefits, and an association with an esteemed company, institution, or organization.

You may have also built up a certain level of personal responsibility or professional goodwill amongst your colleagues, project, or organization. “Some individuals may feel guilty about leaving behind colleagues, a previous employer, or a career they’ve invested a lot of time and effort in,” says BACP accredited psychotherapist Anthony Davis.

Saying goodbye to anything is hard. Starting over is hard. Proving yourself all over again is hard. Rebuilding your reputation is hard. Realizing your past accomplishments may not count for much during the next chapter of your career is hard. And completely disregarding where you could have been if you remained in your former career is hard.

Moving onto something new is often tougher than holding on to what you already have, even when you know deep down that what you have isn’t as good as it gets.

Davis recommends embracing rather than ignoring any feelings of regret or remorse. “It’s important to acknowledge and address these emotions during a career change, seeking support from friends, family, mentors, or professionals when necessary.”

Acknowledging That Change Isn’t Easy Is Half The Battle

If making a career pivot away from an unsatisfying career was simple, everyone would do it. Sometimes, just knowing that the road will be challenging can help normalize the inevitable, emotional roller coaster you experience along the way.

At times, you’ll have moments of doubt. You may feel like you’re lagging your peer group. You may not make progress as quickly as you want. You may even feel a bit jealous when you hear about other people’s professional success stories when you’re still at the beginning of your new journey.

I’ve felt all these things. My clients have expressed similar feelings to me. My audience members and podcast guests share similar sentiments all the time.

Feeling emotional about any change is very normal.

Try to hang in there, and regularly remind yourself why you felt compelled to make this change in the first place. Consider what you’ve already gained just by being on this journey to pursue more meaningful work.

“Allowing ourselves grace, compassion, and understanding will help us move through the process with our self-esteem and identity intact,” says Skinner. “Knowing that we’re making meaningful changes for important personal reasons can help us to face any challenges and setbacks with a self-compassionate approach.”

10 Years Later, I’m So Happy I Made My Leap

On a personal note, despite the initial turbulence I experienced during my shift from corporate employment to self-employment, I honestly can’t imagine feeling any more fulfilled in my career than I do right now.

I love my new professional mission focused on empowering others to bravely pursue work they find more meaningful. I’ve gained so much more than I lost, both professionally and personally. I feel fully engaged with my work. I’m excited to dive into my projects each day. I no longer waste energy comparing myself to others because I feel very personally satisfied and secure with my work and the professional contributions I’m making. I also feel calmer, more collected, and more confident than ever before.

Most importantly, I feel healthy, energized, and satisfied with my life. I’m so happy with the choice I made one decade ago to leave my comfortable job behind, stomach with the discomfort of stepping into the unknown, and find it in myself to pursue work I find more fulfilling.

I hope you’ll do the same.

Originally published at Forbes.

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Joseph Liu
Career Relaunch

Joseph Liu- speaker, career change consultant, and host of the Career Relaunch® podcast focused on helping people do more meaningful work. https://josephliu.co