Here's how you can strategically pivot your career like successful entrepreneurs do.

Before embarking on a new career trajectory, it's imperative to conduct a thorough self-assessment. This entails a candid evaluation of your current job satisfaction, the skills you've acquired, and the market's appetite for your expertise. A brutally honest appraisal of your strengths and weaknesses is essential to gauge the feasibility of your desired career path.

On the topic of market demands, there are numerous resources you can use to see what the trends are like. WIOA (Workforce Development & Opportunity Act) programs offer a comprehensive way to identify current market needs in your area. Be share to check your nearest American Job Center and inquire. Even the front desk can help. O*NET Online is another resource that offers not only the national market trends on particular jobs, but also the skills required for different jobs.

Rather than quelching ambition with a 'reality check', I invite my coachees to describe their vision for their Ideal Self first. Coaching research pioneered by Richard Boyatzis (Intentional change theory (ICT)) showed that envisioning the ideal self enables clients to tap into their own values, strengths, and dreams and to become invested in the change that will help them reach their notion of ideal or best self. So, instead of being motivated to a large extent by external requirements or expectations, they draw on intrinsic motivations for the career pivot. Once the Ideal has been established, I would investigate the gap to the current or 'real' Self.

Taking an assessment of sorts can help you identify your prominent values. Your values are among the most important pieces to defining your goals, because they inform you about what's most important for the time being and even far out in the future, as many values are stable over time. Last I checked, CareerExplorer has a free assessment where you can uncover your key values.

Many times, we mistakenly assume that the new career or opportunity is not for us because we don't have the skills to become successful in that area. Skill gaps can be filled through learning, practice, and working with mentors. Don't shortchange the potential of the career opportunity for lack of skills.

Doubling back to O*NET, the website harbers a plethora of occupations and goes into detail about the knowledge and skills required to get into these jobs. Search for the occupation of your choice and pinpoint the skills you may not have yet. MOOCs and other online courses are more accessible than ever. Be sure to check out places like Coursera, Udemy, or good ole' LinkedIn Learning to get a high-level sense of what you need to learn. These courses tend to be fun, engaging, and have a way of connecting to your previous experience.

If you're able, work with a career professional. A career coach can help you to carefully plan out each step and ensure that you're on the right track. A budget-friendly option, of course, is AI! Large Language Models like ChatGPT or Google Gemini can serve as great guides (when given the right prompts) to help you stay on target.

Execute via reverse mentorship: Reach out with a clear, mutually beneficial proposal. Offer to share your experience and knowledge in exchange for their perspectives and insights.

Regularly ask for feedback from your mentor and others about the impact of the new approaches you’re trying. Use this feedback to adjust your learning and implementation strategies.