As a bit of context, I started my career as a programmer before having the bring 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 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!
Don't believe you are just 1 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.
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.
Not receiving onboarding training/transition to a new leadership role caused a significant challenge during my careers shift. Not having mentorship/guidance made the experience much harder. However, there is always a solution. Some helpful steps that I took to familiarize myself in my role and build confidence included : doing thorough research on the organization and its operations/processes and looking at past histories, actively listening to HR podcasts, getting SHRM membership to stay up to date with HR practices, policies, rules and regulations, and receiving answers from HR professionals, proactively joining HR workshops and virtual trainings (external), and joining HR advisory group, and building my credibility by attending online HR courses and certificate programs. Gradually, I overcame the challenge, and along the way, I built and implemented HR structures/processes within my department that future HR members can utilize and further improve it if need be.
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.
When I transitioned back into editing and writing after taking a break from it for slightly over a decade due to a layoff and then a major move, the most significant challenge I encountered was the increased level of technology. Writing and editing these days involve the need for a working knowledge of several software options, even more so when you're freelancing and working from home. I was new to everything from Slack to ahrefs to ChatGPT to even Clockify. None of those had even been created when I last freelanced. The steps I took to overcome my technological disadvantage were to embrace continued education and dive back into "student" mode to learn these systems by watching training videos, reading instruction guides, taking notes, and studying those notes. With the right attitude, pacing, and patience, as well as encouragement from my employer, I gifted myself with the positivity and confidence to overcome my technological limitations.
I moved from a big company to a much smaller, more entrepreneurial company. 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 down market, robust benefits were trickier, and I had to learn to live with a bit less.
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 two things: 1. My most recent job title matching that of the job I was applying to 2. 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 non-profits. 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. Hope that saves some of you 14 months of job searching!
Challenging your perception of safety. One of my biggest hurdles (and one of the biggest hurdles I see my coaching clients face) is letting go of this idea that being employed in your current job is safer than changing companies or changing career or becoming self employed. The problem with this, is that the thing we deem safe is not always the thing that is right for us or will help us grow. The safe is often the familiar; and 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 again. The more I explored, the closer a new version of safe got for me; flexible, meaningful, varying, balanced. And slowly, I created it.
The most significant challenge I encountered during my career transition came from my old boss. I didn't know it as the time, my old boss had been sabotaging me and my coworkers the whole time. He was threatened by our success and he started to do 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 had my own company 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 opening 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 that was very successful and he sold for a massive profit. If you aren't sure about advice someone is giving you, double check with someone you trust.
A notable challenge in my career transition was managing multiple responsibilities and deadlines, occasionally leading to overwhelming situations. To overcome this, I implemented a prioritization strategy, concentrating on tasks aligning with immediate goals, offering the most direct impact on the transition, and breaking down larger objectives into smaller, manageable tasks, allowing for more efficient time allocation. For instance, I prioritized updating my skills, networking, and tailoring applications rather than attempting to tackle the entire transition process at once. This approach provided a structured plan, enabling me to navigate the complexities of the transition. Each step, meticulously executed, contributed meaningfully to the overarching goal, ensuring a systematic and successful career shift.
Going from a director at a major telecomm with a full team to the CEO of a startup with about 4 people was certainly quite the transition. I knew I was going to need to be significantly more hands on if I wanted to make this work, and that I would need to go into training mode to help the people we were quickly bringing on to get up to speed so we could create a functioning business. It was quite a mindset shift, or as I like to think of it a shift from maintenance to creation.
For me, it was stepping into an entrepreneurial role for the first time. It's quite a big transition from always having someone above you to help set the agenda to having the buck stop with you. What helped me transition into being someone that can thrive in this environment is planning, lots of planning. I planned out, even if only loosely, exactly what I wanted to accomplish, when, how, why, etc. for a fairly long timeframe. It gives you a framework and context for understanding what you're doing rather than just reacting to things, which is the real way to get control over your enterprise.
When I transitioned from a full-time employee to working for myself, I experienced several months of inconsistent income as I was building my business. Not having a consistent salary can take quite the mental toll, especially on someone who is used to earning regular paychecks. To overcome this, I became extremely granular with my budget and made sure that it included a "fun" fund so that I could still enjoy the occasional splurge. This helped keep me in line during the months when business was booming, so that I had extra padding during the months of lower income and could still pay myself the same salary.
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During my career transition, a significant challenge I faced was the skill gap. Transitioning to a new field required new skills and knowledge that I initially didn't possess. To overcome this, I engaged in continuous learning and upskilling. This involved taking online courses, attending workshops, and obtaining certifications relevant to my new field. I also made it a point to network with professionals in the industry, which provided me with valuable insights and opportunities for mentorship. Gaining practical experience was crucial too, so I took on internships, volunteer work, and part-time roles. These steps were instrumental in bridging the skill gap and facilitating a successful career transition.
A significant challenge during my career transition as a business expert was battling Impostor Syndrome. I consistently felt inadequate in my new field. To combat this, I began meticulously documenting my daily achievements, no matter how minor, to build tangible evidence of my progress. Furthermore, I sought unconventional mentors who brought diverse perspectives and unique strategies to the table, allowing me to develop an extraordinary skill set and mindset not typically seen in my industry. By addressing Impostor Syndrome directly and adopting unorthodox mentorship and self-validation methods, I effectively managed my career transition and thrived as a business expert in my new domain.
Transitioning to a new career path can be daunting, but one significant challenge I faced was adapting to the demands of digital customer service. To overcome this, I actively sought insights from industry experts and implemented key strategies such as embracing seamless integration, providing hyper-personalized communication, and prioritizing a dedicated customer service team. Additionally, I focused on understanding the ideal customer profile and journey, which enabled me to anticipate customer needs effectively. By combining technology with a human touch, I was able to enhance customer convenience, personalization, and loyalty, ultimately overcoming the challenges associated with the transition and achieving success in the digital customer service realm.
One significant challenge I encountered during my career transition to the COO position at Promotional Product Inc. was bridging the gap between my technical expertise and the broader business acumen required for the role. Having spent my early career focused on the technical aspects of online marketing and promotional products, I needed to expand my knowledge of business strategy, finance, and leadership. To overcome this challenge, I embarked on a continuous learning journey. I enrolled in executive education programs, attended industry seminars, and actively sought mentorship from experienced business leaders. This proactive approach to learning proved invaluable. I acquired the necessary business knowledge and skills, enabling me to effectively navigate the complexities of my position. My ability to bridge the technical and business domains has been instrumental in driving growth and innovation at Promotional Product Inc.
Earlier this year, I switched from an in-house role to full-time freelancing in January this year. My biggest challenge was the fact that I was the worst boss I ever had. As soon as I started working on my business, the lines between what's work and what's free time got blurred. I started overworking myself, setting extremely high output expectations, and being quite harsh on myself when I didn't meet them. In May, I realized that I was on the path to burning myself out so I started setting some boundaries. It's still a struggle, but here are some rules that help me create a better balance: 1. No phone or laptop checking in the first hour of waking up or in the last hour of the day 2. No work on leisure trips 3. I take at least one full day off per week 4. Daily calming practice (it could be meditation, breathwork, journaling, etc.)
Navigating the Challenge of Transitioning from Writing to Digital Marketing One significant challenge I encountered during my career transition was adapting to a new industry with different technical requirements. Coming from a background as a writer, I decided to transition to digital marketing. The shift required me to acquire a new set of technical skills and a deeper understanding of marketing aspects. To overcome this challenge, I took several proactive steps. First, I enrolled in online courses to gain foundational knowledge. Additionally, I sought out mentorship from experienced marketers who provided valuable guidance and insights. Networking became a crucial part of my strategy; attending industry events and connecting with professionals in the marketing field allowed me to build a support system.