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We often hear about career-ending mistakes: the ethical breach, the catastrophic project failure or an unforgivable snafu. But there's another, far more insidious career killer that affects a much wider swath of professionals: failing to plan the end of our careers.
And by "end," I don't just mean choosing a retirement date. I'm talking about the aim, the goal, the ultimate destination of your professional journey. Where do you want to be when you finally say, "This is it. This is where I've always wanted to be"?
If you're in a role you love and never want to leave, congratulations! You've arguably reached the end of your career, even if you continue working for decades. But if, like most of us, you're not quite there yet, it's crucial to ask yourself:
What job would you truly love?
How are you going to get it?
Where do you want to end up?
Is your current trajectory leading you there?
If not, what changes do you need to make?
Out of Control: The Chaotic Nature of Careers
The word "career" has an interesting origin. It can mean "to rush about wildly" or "to move fast and out of control," much like a vehicle careening down a road. Doesn't that resonate with the experience of many professionals?
The indispensable first step to getting what you want is this: decide what you want.
Ironically, most of us don't truly know what we want to do until we're already doing it. By the time we've clarified our goals, we may find ourselves far down a less-than-ideal path. It's no wonder, then, that many end up in unsatisfying jobs with limited prospects. Happiness in our careers often feels like a matter of luck rather than deliberate design.
Perhaps it's time to shift from wild, uncontrolled rushing to thoughtful planning. We often meticulously plan projects and tasks. Shouldn't we give at least a fraction of that attention to the "program" we're writing for our own lives?
The best time to start a saving for retirement is always twenty years ago, and career planning is similar. By the time the need becomes apparent, you often wish you'd started sooner. But don't let that discourage you. Even a late, imperfect plan is better than no plan at all.
So, what does a career plan look like, and when should you start crafting it?
Early Career: This phase is for exploration and experimentation. Mistakes are less consequential, and there's ample room to learn and adapt.
Mid-Career: This is the prime time for planning. You have enough experience to understand your strengths and weaknesses, and enough time to make significant course corrections.
Late Career: Options become more limited, and major shifts are harder to execute. The autopilot tends to take over, guiding you along your existing trajectory.
Ideally, you should be planning to enter the final phase of your career in the right position, at the right level, and at the right time to land where you want to be.
Three Kinds of Careers: Seniority, Management, Independence
Your ideal career path might involve a combination of different roles and experiences. To simplify things, let's consider three broad categories of career destinations:
Seniority: Reaching the top of your field as an individual contributor (IC).
Management: Leading and developing teams of people.
Independence: Working for yourself, either as a consultant, freelancer, or business owner.
Seniority: The Path of Mastery
The first destination we'll explore is that of the senior individual contributor (IC), a highly skilled expert in their field.
Senior ICs are at the pinnacle of their craft. They may mentor others, offer expert advice, but they primarily focus on doing the work, not managing others who do it.
Specific titles and ranks vary, but we're talking about the highest level you can reach while remaining primarily focused on your area of expertise. This is not an executive role. You won't have a corner office or a board seat. But you'll likely enjoy high pay, status, authority, and you'll spend your time doing the work you love.
Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.
What They Don't Do:
Senior ICs typically don't get to choose their projects and may disagree with decisions made by management (often because they have deeper subject matter knowledge). While you can switch companies if you're unhappy, you'll likely encounter similar dynamics elsewhere.
Who It's For:
This path appeals to those who want to remain deeply involved in their field of expertise, avoiding the political and administrative burdens of management or business ownership.
How to Get There:
Investigate: Understand the senior IC landscape in your company or field. Talk to senior ICs, learn about their journeys, and see if their reality matches your aspirations.
Communicate: Tell your boss about your ambition. Seek their support and understand their expectations. Maintain an ongoing dialogue, checking in regularly on your progress.
Take Ownership: Don't wait for the company to train you. They prefer to promote those who are already performing at the next level. Take personal control of your skills development and become a master of your craft. Consider working with a professional coach.
Manhood is patience. Mastery is nine times patience.
Management: The Path of Leadership
While senior ICs can earn substantial salaries, the highest levels of pay and responsibility within an organization are usually reserved for management.
The Natural Progression (But Is It Right for You?):
For many, management seems like the default next step in their career progression. But is it a path you truly want to follow?
What Does a Manager Do?
Managers need a solid foundation of competence in their field, but their primary focus is on leading, supervising, hiring, and developing other people. These are all distinct skills, and surprisingly rare ones.
The Difficulty of Management:
Managing people is arguably harder than many technical tasks. While equipment and processes follow instructions (even if those instructions are wrong). People are far more complex. Not everyone can become a truly effective manager. In fact, many managers are, frankly, terrible at their jobs.
The Value of Great Managers:
Good managers, like good teachers, are rare and invaluable. If you've had a truly great boss, you'll likely remember them fondly and perhaps even try to emulate their leadership style. While managers may not be directly involved in the hands-on work, they can significantly impact the success of projects and organizations.
Becoming a Great Manager:
If you aspire to be a great manager (and I believe that's the only kind worth being), start practicing now:
Develop People Skills: Learn about communication, collaboration, and psychology. Understand what motivates different individuals.
Manage Yourself First: If you can't organize and manage yourself effectively, how can you expect to lead a team?
Study Your Manager: Observe your own manager. If they're effective, analyze what makes them so. If they're not, identify their shortcomings and consider how you would do things differently.
Become a De Facto Leader: Start taking initiative to help your team members, anticipate problems, and facilitate solutions. You might find that you naturally become the go-to person for your colleagues, even without a formal leadership title.
Independence: The Path of Autonomy
Independence means working for yourself, likely in your own company, potentially with employees, but possibly solo. However, simply being a one-person company doesn't guarantee true independence. The distinction between a consultant and a contractor is crucial:
Consultant: Tells the client what to do (independent).
Contractor: Is told what to do by the client (not independent).
The Pros and Cons:
Running your own business or being an independent worker offers great freedom and autonomy. But it also comes with challenges:
Pros: Be your own boss, set your own schedule, choose your projects, potentially earn more.
Cons: Marketing, sales, accounting, irregular income, no benefits (vacation, insurance, sick pay).
When It's Time to Leave (or Be Pushed):
If you're considering a transition to independence, careful planning is essential. Quitting your job impulsively is rarely a good idea. Timing is important, as is having a solid foundation of skills and experience.
Lao Tzu teaches: the best fighter is never angry. More important than the blow is knowing when to strike. Like, perhaps, after we experience the executive whitewater rafting trip in Coeur d’Alene.
Before taking the leap, consider dipping your toe into independent work through side gigs. This allows you to gain experience, build a client base, and assess whether self-employment is truly right for you.
Layoffs, while unpleasant, can sometimes be a blessing in disguise. If you've always dreamed of independence but lacked the courage to leave your job, being forced out might be the push you need.
Making the Choice: Combining Paths and Finding Your Fit
I hope this article has sparked some reflection on your career trajectory (writing this has definitely sparked a lot of ideas). You might not have all the answers yet, and that's perfectly normal.
Key Considerations:
You're not limited to just one of these paths. Many successful careers blend elements of seniority, management, and independence.
Your ideal path might involve being a part-time manager and running a side business, or being a highly specialized consultant within a larger organization.
You might even become the CEO and lead expert in your own company, combining all three paths.
Reflect on your values, your strengths, and what truly motivates you. As you gain experience and learn more about yourself and the world, your career aspirations may become clearer.
Tell me, what is it you plan to do With your one wild and precious life?
Your future might not even lie within your current industry. Many successful professionals have transitioned to entirely different fields, finding fulfillment in various pursuits.
Once you have a general sense of your desired destination, you can start making small adjustments to your course. You don't need a rigid, step-by-step plan. Life is unpredictable. Instead, be flexible and adaptable.
You can’t stop the waves, as the saying goes, but you can learn to surf. Chance favours the prepared mind.
Having a plan, even a flexible one, helps you recognize and seize opportunities when they arise. If you've never thought about what you want, how will you know when you've found it?
Principles for a Successful Career Journey
Here are some guiding principles that have emerged from successful individuals' experiences (points 7 onwards is for later careers):
1. Dots, Not Ladders
Early in your career, focus on gathering "dots" (experiences, skills, connections) rather than climbing a rigid career ladder.
2. Maximize the Slope of Your Learning Curve
Choose opportunities that offer the steepest learning curve, regardless of prestige or immediate financial rewards.
3. The 6-Month Rule
Commit to any new role or project for at least six months before deciding whether to stay or move on.
4. Learn How to Think, Not What to Think
Develop strong mental models and critical thinking skills that can be applied across various domains.
5. Focus on People, Not Just Ideas
Cultivate relationships with talented and enjoyable colleagues. These connections will be invaluable throughout your career.
6. Choose Your Boss Wisely
In the middle years of your career, your boss can have a significant impact on your growth and opportunities.
7. Find Your Fit
Seek work that aligns with your passions, strengths, and market demand.
8. Build Your Brand
Develop a strong personal brand that reflects your expertise, values, and unique contributions.
9. Unlearn, Transform, Re-Invent
Be prepared to unlearn outdated knowledge and adapt to new technologies and approaches, especially in the later stages of your career.
10. Masterful Exits
Plan your exits as carefully as your entrances. Leave on a high note, maintaining positive relationships with former colleagues.
11. Build a Portfolio Career and Give Back
In your later years, consider diversifying your work and giving back to your community through consulting, advising, mentoring, or teaching.
By embracing these principles, you can navigate the complexities of a multi-decade career with intention, purpose, and a greater chance of achieving lasting fulfillment.
