Executive Challenge #3: “I’m Unsure Where My Career Is Headed.”

by | Executive Coaching for Better Leadership Success

What are the biggest challenges facing successful business people today? In my work as a certified executive coach for C-Suite Executives, Directors, Managers, and Entrepreneurs, there are many recurring themes that seem to surface. One at a time, I’ll be sharing with you 12 of those top challenges along with hints, tips, and steps you can take to avoid or eliminate altogether these key issues that might be holding you back from achieving the kind of success you are aiming for.

Challenge #3: “I’m unsure where my career is headed.”

Let’s face it: These are tough times in the lives of executives. The markets are topsy turvy, layoffs are rampant, stock options are underwater, and people are running scared. For expatriates, add in the complexity of living outside your home country, and all of this can leave you wondering where you’re headed and worried about a future that is increasingly murky and unclear.

If you’re like most executives, it’s hard to find the time to sit down and contemplate where your career is going. You’re busy taking care of day-to-day operations, and there are only so many hours in a day. It takes time and effort to focus on your future, and it’s easier just to live from one moment to the next.

But, if you don’t make the time to determine your future, who will? At the senior manager or executive level, you are — yourself — the best person to look at the big picture and set the direction for your next move. You are no longer at a level where you can leave your fate to “the powers that be” at headquarters or to your immediate boss.

If your future career direction was any other type of business challenge, you would face it head-on, wouldn’t you? You’d spend time working on it, approaching it from all angles, enlisting assistance, and putting a plan of action into place. Well, the future of your career is no different – it deserves the same time and effort.

Your “Career Mini-Retreat”

As a coach, I see executives every day who have put off reaching their full potential. They put everything else ahead of long-term career objectives. So, I suggest you take a “career mini-retreat.”

Set aside as many hours as you need to focus on nothing but your career. Make sure the kids are gone and that your cell phone is off. Find a quiet space where you won’t be interrupted, not even by e-mails. During this time, focus on answering the following questions honestly and in-depth:

  1. Look at your career from a 35,000-feet-in-the-air perspective. Where are you in the big-picture scheme of things? If your entire career were a project timeline, where in that project do you find yourself now? Are you still in the early stages based on what you had hoped for yourself? Are you just a few years from retirement and have not yet achieved what you wanted?
  2. Now, focus on your current position at work. What do you enjoy most about the position you hold now? Why? Likewise, consider what you dislike and would change tomorrow if you could. Why? Make a complete list of both.
  3. Next, look back into your career history, and compile a list of all of the key positions you’ve held in the past. What did you learn from each of those jobs? What skills did you pick up along the way? What were your failures, and how did you evolve and grow as a result of them? What did you enjoy most, and what did you dislike about each of these positions? Make a complete list for each former key position.
  4. Finally, allow yourself to think about the future, but don’t focus on possible ‘job titles.” These can limit your thinking and put you in a box. Instead, think of what skills you’d like to develop. What interests have you not yet explored in a work context? What new experiences in your industry or career would compliment your existing portfolio? What elements of your own personal development would you like to improve at this stage in your journey as a senior manager or executive?
  5. Armed with this complete and constructive self-analysis, list all possible options that you could explore as a next step, such as:
    • Stay in your current position, and focus on improving one particular area of your own management development.
    • Stay in your current position, and add another related area of responsibility that will help grow your portfolio.
    • Find a new position within your current company that carries more responsibility or which will bring you new challenges to help you grow as a leader.
    • Find a new position in a new company, marching to the beat of a different drummer altogether.

Some clients learn through coaching that they can reinvigorate the way they feel about their current position with just a few minor alterations, while others discover that they have outlived or outgrown their current firm. They may decide it’s time to move on to a completely new environment with challenges that ‘fit’ them better. Others come to the conclusion that the corporate environment is no longer appealing, and it’s now time to start their own business.

Whatever you find out, you will never move forward unless you take the time to evaluate where you are compared to where you want to be. Take all the time you need to do it right.

Leading You Book Cover


The most important driver of overall success is your own self-leadership. How you lead yourself directly impacts your ability to lead others, and that, in turn, can prevent you from reaching your full potential.

Discover the power of SELF-LEADERSHIP to build your executive brand and drive career success.

Brenda Bence is sought after across six continents as a Certified Executive Leadership Coach, internationally recognized branding expert, and the author of 11 award-winning books on leadership, coaching, and branding. A Global Certified Speaking Professional, Brenda is in demand as a top-rated motivational speaker, engaging audiences around the world, both in-person and virtually.

Recognized by Thinkers50 as a World Leader in Coaching, Brenda is also consistently ranked by Global Gurus as both a Top Ten Professional Coach and a Top 10 Branding Guru.

After earning her MBA from Harvard Business School, Brenda spent the first part of her career as senior executive in Fortune 100 multinationals, building brands across dozens of countries that spanned four continents. Now, as President of her own company and with offices in both Singapore and the United States, Brenda has transformed audiences and individual coaching clients around the world to help them achieve greater success through building inspiring leadership brands – from the inside out.

Visit www.BrendaBence.com to learn more.

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