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13 Common Challenges Faced During a Career Transition and How to Overcome Them

Career transitions come with their unique set of challenges, and to navigate them, we’ve gathered insights from thirteen leaders, including CEOs and COOs. From grappling with financial stability in freelancing to learning business skills through online courses, these professionals share their personal hurdles and the strategies that propelled them forward.

  • Grappling with Financial Stability in Freelancing
  • Combining a Strategic Resume and Skill Enhancement
  • Adjusting to Smaller Company Benefits
  • Correcting Course with a Business Coach
  • Self-Guided Leadership Onboarding
  • Moving from Finance to Entrepreneurial Versatility
  • Leveraging Networks for Career Change
  • Redefining Identity Through Brand Creation
  • Developing Resilience in Leadership
  • Challenging Safety for Career Growth
  • Transitioning to a People-Centric Role
  • Overcoming Technological Learning Curves
  • Learning Business Skills Through Online Courses

Grappling with Financial Stability in Freelancing

When I decided to transition from a stable corporate job to pursuing writing full-time, the unpredictability of freelance income was a major challenge. I went from a regular paycheck to fluctuating month-to-month revenue that spiked my anxiety.

To overcome this hurdle, I created a substantial emergency fund to cover expenses during income dips. Building a financial cushion was essential for peace of mind. I also diversified my income streams—from books to speaking engagements and consulting gigs. Having multiple revenue sources allows me to withstand the ups and downs. Being diligent about tracking income and expenses helps me manage my finances and stay profitable.

With the right preparation and systems in place, I’ve been able to power through the uncertainty that comes with career changes. Having a plan gave me the confidence to take the leap.

Vikrant ShauryaVikrant Shaurya
CEO, Authors On Mission

Combining a Strategic Resume and Skill Enhancement

It took me 14 months to complete my career transition. What I realize now is that it could have been a lot shorter if I had known two things.

Everything changed for me once I actually spoke with the recruiters who were rejecting me. What I found out was that they were looking for my most recent job title matching that of the job I was applying to, and a few keywords on my resume matching the skills on their target list.

To secure the first, I volunteered for some projects with a couple of local nonprofits. This allowed me to put that target title on my resume. Then, I took a few courses on Udemy and LinkedIn Learning. I added those skills to my resume and quickly started matching for those keywords they wanted.

If you’re trying to make a career transition, these two things are must-haves, not nice-to-haves. I hope that saves some of you 14 months of job searching!

Bogdan ZlatkovBogdan Zlatkov
Lead Instructor for HR and Hiring, Growth Hack Your Career

Adjusting to Smaller Company Benefits

I moved from a big company to a much smaller, more entrepreneurial one. It was easy to take robust benefits for health insurance and lifestyle for granted. Big employers have great negotiating power, and they know it’s a great thing to offer employees for retention. As I transitioned to a smaller market, robust benefits were trickier, and I had to learn to live with a bit less.

Trevor EwenTrevor Ewen
COO, QBench

Correcting Course with a Business Coach

The most significant challenge I encountered during my career transition came from my old boss. I didn’t know it at the time, but my old boss had been sabotaging me and my coworkers the whole time. Our success threatened him, and he did things that would eventually slow our progress down as humans and his employees. Thankfully, I realized a few years later that almost everything he taught us about how to treat prospects and customer service was wrong.

A few years after I left his company and started my own, I hired a business coach. We went over everything in my entire business together, including how we conducted sales calls and customer service.

Wow, was that an eye-opener and so extremely helpful. My coach told me that what we were doing was the exact opposite of what he did when he owned his company, which was very successful and he sold for a massive profit. If you aren’t sure about the advice someone is giving you, double-check with someone you trust.

Ben WalkerBen Walker
CEO, Ditto Transcripts

Self-Guided Leadership Onboarding

Transitioning to a new leadership role without receiving onboarding training posed a significant challenge during my career shift. The lack of mentorship or guidance made the experience much harder. Nevertheless, there is always a solution.

To familiarize myself with my role and build confidence, I took several helpful steps: conducting thorough research on the organization and its operations/processes, examining past histories, actively listening to HR podcasts, obtaining an SHRM membership to stay current with HR practices, policies, rules, and regulations, and seeking advice from HR professionals. I proactively participated in HR workshops and virtual trainings (external), joined an HR advisory group, and built my credibility by attending online HR courses and certificate programs.

Over time, I overcame the challenge and, in the process, developed and implemented HR structures/processes within my department that future HR members can utilize and refine if necessary.

Dalamu SherpaDalamu Sherpa
HR Director, I’RAISE Girls & Boys International Corporation

Moving from Finance to Entrepreneurial Versatility

Don’t believe you are just one job or career. I studied finance and started my career in the field but ended up changing my career trajectory a few times because I had built up a lot of skills over time that did not allow me to be just a financial analyst, now I am a well-rounded entrepreneur with a deep set of skills that can work in any part of the world.

Derek CapoDerek Capo

Leveraging Networks for Career Change

Seasoned professionals spend years building a network with their peers in case they need to change companies. This network is essential for success in most management positions, and it’ll be the thing you miss the most in a new career.

You should still leverage the old network and see if you can get a few introductions. All you need is one solid connection to kick-start your new career, or one good referral to land a job. There’s no shame in leveraging old contacts to build new ones. Additionally, ask your colleagues to help build your account on LinkedIn—it’ll help attract professionals in your new field.

Perry ZhengPerry Zheng
Founder and CEO, Pallas

Redefining Identity Through Brand Creation

Embarking on a journey from a corporate job to launching my sportswear brand, the biggest hurdle was the unsettling feeling of losing my professional identity. Accustomed to being recognized by my former role, I found myself adrift in a sea of unknowns.

To anchor myself, I embraced the ethos of the very lifestyle my brand promotes: resilience. I set daily goals, whether that was a design sketch or a business connection, to foster a sense of accomplishment. With each step, no matter how small, I redefined my identity, not by a job title, but by the passion and vision I was pouring into my new venture.

Jay BartonJay Barton
CEO and Founder, ASRV

Developing Resilience in Leadership

Transitioning to the role of President in my company presented a unique challenge with cultivating mental and emotional resilience. Initially, I found the shift overwhelming, facing an array of unfamiliar responsibilities and high-stakes decisions.

To overcome this, I embraced a two-pronged approach. First, I sought mentorship from experienced leaders within our industry, gaining invaluable insights and strategies. Concurrently, I committed to personal development, engaging in mindfulness and resilience training. These steps bolstered my confidence and enhanced my decision-making skills, proving crucial in navigating the complex dynamics of this leadership role.

Sandra MaloufSandra Malouf
President, Eurolog Packing Group

Challenging Safety for Career Growth

Challenging your perception of safety is one of my biggest hurdles—and one of the biggest hurdles I see my coaching clients face. It involves letting go of the idea that being employed in your current job is safer than changing companies, changing careers, or becoming self-employed.

The problem with this is that the thing we deem safe is not always what is right for us or what will help us grow. What is safe is often the familiar; it is also the thing keeping us stuck and unhappy. Is it really safer to be unhappy and stuck?

To challenge this, I redefined “safety” from being something I know to being something that feels aligned. I spent a lot of time exploring what that alignment would look and feel like: journaling, coaching, talking to people in different kinds of jobs—I even worked in a cheese shop for a bit to open my mind about what work could be. The more I explored, the closer a new version of safe got for me: flexible, meaningful, varied, balanced. And slowly, I created it.

Hannah RayHannah Ray
Life, Career + Business Coach, TAKE Coaching Amsterdam

Transitioning to a People-Centric Role

Transitioning from Project Manager to an HR Director role posed a notable challenge: moving from a results-oriented mindset to a people-centric approach.

To surmount this, I actively sought HR-specific training, collaborated with seasoned HR professionals for insights, and focused on developing empathy and emotional intelligence. Applying project management efficiency to HR processes, I streamlined operations while maintaining a human-centric focus.

This experience underscored the value of adaptability and continuous learning in successfully navigating career transitions and bridging diverse professional domains.

Hanna BorysenkoHanna Borysenko
HR Director, Elai Inc.

Overcoming Technological Learning Curves

Transitioning back into editing and writing after a decade-long hiatus due to a layoff and a major move presented a significant challenge: the advanced level of technology required in the field.

Nowadays, writing and editing demand familiarity with various software tools, especially for freelancers working remotely. I had to acquaint myself with everything from Slack to Ahrefs to ChatGPT to Clockify, none of which existed during my previous freelancing stint.

To bridge the technological gap, I committed to continuous learning, adopting a “student” mindset. I immersed myself in training videos, instruction guides, and note-taking, thoroughly studying the material. A positive outlook, steady pace, patience, and support from my employer equipped me with the confidence to surmount my technological hurdles.

Michelle RobbinsMichelle Robbins
Licensed Insurance Agent,

Learning Business Skills Through Online Courses

I started my career as a programmer before having the bright idea to stick a tablet to a wall to see if a conference room was busy or not, which led to me starting Yarooms. When I started the business, I knew the product and extremely little else about actually running a business. It was a whole new and unfamiliar world, one that I was determined to figure out.

The way I did it was through a copious amount of online classes. Sounds simple, but there is extremely little out there that you cannot learn in a few months with good enough online courseware from Coursera, Pluralsight, and the like. I took an intro to sales class and was using the coursework in my business at the same time I learned it!

Dragos BadeaDragos Badea
CEO, Yarooms

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