The Leaps That Shaped Me: From Ladder Climber to Founder and Back Again
Why I leapt away from the corporate herd twice - only to come back stronger
Perched at the edge of the high dive, every muscle tensed, anticipating the freefall into the pool below. With my toes curled, clutching the cold metal rail, I could barely catch a full breath. My heart threatened to hammer through my chest as familiar doubts screamed to head for the ladder.
But something deeper compelled me to fling myself into the void anyway, again and again. Call it blind courage or just plain stupidity.
Turns out that audacious impulse prepared me for so much more than backflips off the high dive. It gave me the guts to catapult my career into the unknown three times.
The central theme of this article is about that very leap – how fear can tether us to the familiar and how we can sever those ties to pursue our happiness. We’ll explore the benefits of career transitions, common fears and challenges, and strategies for successfully navigating these changes.
The Benefits of Career Transitions
Career transitions can be transformative. I’ve seen it firsthand in my journey from a Senior Project Manager at KPMG to a VP of Strategic Planning at Renova Energia to growing a successful Startup App, ClickSitter, with over 10,000 paying users. Each transition was a step into the unknown. Still, it led to personal growth, satisfaction, and a sense of fulfillment that I could not have imagined.
I remember the day I decided to leave my job in manufacturing. I was sitting in my office, staring at the same four walls I’d seen daily for the past five years. I had a good job, a steady paycheck, and a clear career path. But I wasn’t happy. I felt stuck and unfulfilled, and I knew I wanted more. That’s when I realized fear was the only thing holding me back from pursuing happiness.
Successful career transitions are not just my story. They are everywhere, from the lawyer who becomes a pastry chef to the accountant who launches a tech startup. These stories are not anomalies; they are evidence of the positive outcomes that can come from embracing change. Research and expert opinions back this up, suggesting that career transitions can significantly improve happiness and well-being.
Career transitions can lead to personal growth, satisfaction, fulfillment, and impact. They can open up new opportunities, challenge us in new ways, and help us discover our true passions. Research shows that people who make career transitions often report higher levels of happiness and well-being.
The Common Fears and Challenges of Career Transitions
Despite the potential benefits, the path to a new career is often fraught with fear. The Holmes-Rahe Life Stress Inventory ranks changing to a different line of work just below the death of a close friend in terms of stress. Financial insecurity, the uncertainty of stepping into the unknown, the possibility of rejection, and the fear of failure are formidable obstacles.
Fear can manifest in various forms: fear of the unknown, fear of losing status, fear of disappointing others, and fear of regret. These fears can paralyze decision-making, sap motivation, and erode confidence. However, acknowledging these fears is the first step to overcoming them.
But career transitions are not without their challenges. There’s the financial insecurity, the uncertainty, the risk of rejection, and the fear of failure.
Fear is a powerful force. It can paralyze us, keep us stuck in our comfort zones, and prevent us from pursuing our dreams. There’s the fear of the unknown, the fear of losing status, the fear of disappointing others, and the fear of regret.
I remember the fear I felt when I left my job in manufacturing. I was stepping into the unknown, leaving behind a secure job for a career in an industry I knew nothing about. But I also knew that if I let that fear control me, I would never find something different, and I accepted the risk that maybe it was not it yet.
Why I Blindly Jumped from 6 Figures to a Scrappy Startup
There I was, in a fancy office with a lavish salary to match. From the outside, I appeared to be living the dream as the Head of Strategic Planning at a prestigious energy-renewable company.
But after three years behind my shiny designer outfits and weekend getaways, I hid an unshakeable sense of emptiness, not because of the work per se but driven by my absence as a father of two amazing little girls. So, day after day, I stared at the same four walls, day after lifeless day. I knew there had to be out there which could give me a better work-life balance. But I was just too scared to admit it.
So I stuffed down that nagging little voice yearning to take a flying leap into the unknown. At first, my desire was to take a sabbatical year. But, until one day, the fear of missing out finally eclipsed the fear of failure.
I realized that if I never sacrificed the golden handcuffs for my family and started something on my own, I would for sure spend my whole life regretting it.
So, I took the plunge into the abyss, draining my savings to launch ClickSitter, but this is a story to another article. Let’s just say things got messy.
Tips and Strategies to Overcome Fear and Succeed in Career Transitions
I’ve transitioned between careers three times now. While each journey has been uniquely challenging, I’ve picked up some concrete tactics along the way.
Conduct a 360 Self-Assessment First
I’ve transitioned my career thrice and learned something new about overcoming fear each time. One of the most effective strategies is to prepare thoroughly. Before even peeking at job boards, I needed crystal clarity on my own skills and passions.
I spent one whole month going through the following self-discovery process:
Took online assessment tools like the Leadership 360 and CliftonStrengths to reveal strengths and growth areas
Completed writing prompts digging into peak career experiences when I felt fully energized and engaged
I mapped my skills matrix - rating proficiency in areas like data analysis, programming languages, project management, etc.
Interviewed 30 close contacts to get external perspectives on my talents
This intensive self-reflection armed me with granular insights I could match to potential careers while benchmarking current skill gaps that need development.
Tap Your Network for Informational Interviews
Next, I tapped my network to set up informational interviews with 5-7 people in my desired fields. I made sure to understand:
Their career progression and lessons learned
Objectives and key performance metrics in their roles
Technical abilities or credentials required or preferred
Advice on transitioning into the industry, given my background
Invaluable nuggets from informational interviews helped me further focus my goals and create a tailored skilling-up strategy.
Seek Out Entry Ramps Like Volunteering or Courses
Finally, I looked for short-term ways to start building relevant experience. Local startups often took on marketing volunteers for 3-6 months. I completed digital certifications like Google Analytics and Facebook Blueprints. Entry-level freelance gigs let me flex new muscles.
Psychologically, there are techniques to manage fear. Reframing your perspective to view challenges as opportunities, using visualization to imagine success, employing affirmations to bolster self-belief, and practicing mindfulness to stay grounded can all help. These techniques have supported me and many others I’ve mentored through career changes.
Embracing a pivotal approach in my journey has been the profound realization that my career and personal happiness are solely my responsibility. I’ve learned to prioritize my own convictions over external opinions, recognizing that ultimate accountability rests within me. This empowered mindset has allowed me to navigate my path with authenticity and purpose, focusing on what truly matters in pursuing my professional and personal fulfillment.
Overcoming fear is not easy, but it’s possible. I’ve done it three times and helped others do it, too.
Learning new skills is another essential step. In my transition from construction to manufacturing, renewable energy, and technology, I had to learn about strategic planning, project finance, digital marketing, SEO, and content creation. It was challenging, but it was also exciting and rewarding.
Try reframing, visualization, affirmations, and mindfulness to cope with fear. These techniques can help you change your perspective, visualize your success, affirm your abilities, and stay present and focused.
Fear is a powerful force that doesn’t have to control us. We can overcome it and pursue our happiness through career transitions.
To wrap up, career transitions are a leap of faith, but one that can lead to a more fulfilling and happier life. The benefits, though sometimes obscured by fear, are authentic and attainable. You can successfully navigate your career transition by understanding the common concerns and challenges and employing practical and psychological strategies.
And be sure of one thing: A lot of people will not understand why you are transitioning, and they will label you as crazy or, even worse that are inconsistent. I learned from it, and I don’t care if people judge me because I dared to take the risk to pursue it.
Career transitions can lead to personal growth, satisfaction, fulfillment, and impact. They can be challenging, but they can also be successful with the right strategies and mindset.
As we part ways, I leave you with this thought: What would you do if you weren’t afraid? Let that question guide you as you consider your next career move. And remember, on the other side of fear lies your potential for happiness. Are you ready to take the leap and rewrite the next chapter of your career?
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