The Career Bucket List: 10 Ideas to Round Out Your Career

As we progress in the journeys our lives, we go through a continuous process of self-development. The more accumulated experiences we have to draw from, the more we are able to figure out what we like/don’t like, what we want more/less of, and where we might want to go next. The more diverse a pool of experiences we have to draw from, the more material we have to help us understand what life experiences are meaningful to us, and which directions we wish to go moving forward.

This happens with our careers, too. The more diverse a set of work experiences we gain, the better we are able to realize what work we like, don’t like, what want more of, less of, and so on.

Consider the following list of 10 career-related suggestions as an early-to-mid career bucket list, which can give you the diversity of experiences to figure out what you want to do with the remainder of your career.

Note that these are only suggestions. Everybody is different, and so not all of these will make sense to you.

For instance, some people enjoy their company and work so much that they stay there for decades.

Others would be content never to work for themselves if they don’t have an appetite for risk, or just prefer to invest their energies into life outside of work. That’s great, too!

Exploring can be very helpful, but at the end of the day there’s no right or wrong way to develop your career, and there’s no single standard approach. You innately know what’s best for you. Take a browse, see which of these elicits a gut “I’m interested in that” for you, and consider explore that idea(s) more deeply.

1: People Management

Managing people can be very rewarding, and is one experience many people will end up pursuing.

Especially if the idea of serving others, supporting the development of others, driving a scaled impact, holding others accountable, guiding and organizing, collaborating, and counseling, then be sure to pursue a manager role!

However, also know that it is not true that in order to continue advancing your career or to become a leader, you must become a manager. You can certainly achieve all of the above desires and continue growing your career, all without having direct reports. Leadership is about setting a vision or goal, and guiding others towards realizing that vision or goal, which can be done as an individual contributor, too.

Also, taking a management role isn’t a permanent decision you make once that defines your track for the the rest of your career. Contrary to what is still a dominant career fear, it’s okay to step back from management after trying it out if it’s not for you, or not the right time. You won’t be a failure. People do it all the time! Be honest, be decisive, and appreciate the fact that you realized that there was a better fit for you elsewhere. You can also go back to management later on if you find that it’s an experience you want once more.

2: Work for yourself

Working for yourself can bring a lot of freedom and allow you to move fast, and if this is appealing to you, then explore the option of working for yourself.

Working for yourself may mean starting a company, taking funding, and scaling a business/team/product in the Neo classic startup founder example, but it doesn’t have to mean that.

You can also become a freelancer, consultant, start an online store/shop, run a pop-up store, become a solopreneur, or start a bootstrapped company, or start a small business and keep it small.

3: Teach others/give back

Especially as we move out of the early stages of our careers and into the mid-to-late stages, the desire to give back and support the journeys of others becomes more important for many people.

The easiest place to start is within your organization through a new role, a stretch project, job crafting (changing your job responsibilities to do more of what you enjoy), or by raising your hand to mentor or train others.

If you desire to connect with others beyond of your organization, then explore opportunities by training others, teaching, coaching, mentoring, advising, becoming a board member, or volunteering. This can tie in nicely with trying out working for yourself, too.

You can also share what you have learned by writing a blog or book, creating a social media channel, starting a podcast, creating an online course, presenting at a conference or webinar, participating in an online Ask Me Anything, or sharing an email newsletter.

4: Create a lasting impact

Like teaching others and giving back, finding some way to leave a lasting impact or legacy becomes an important milestone that many people desire as their careers progress.

  • Perhaps it is to lead the creation of a documentation

  • Or to write a book (such has Ray Dalio’s book, Principles)

  • Maybe it means creating a new business, a new team, or a new product

  • It could also mean starting your own company, or joining an early-stage company and helping to grow it

Try sitting down one day when you have enough mental space and time to reflect and get creative (a vacation is a good time). Use a whiteboard or notepad, and write “my lasting impact” in a circle in the center. Write any ideas (it can even be just words for now) that come to mind that relate to the topic of your impact. Revisit this brainstorm for several weeks or months, continuing to add to it and letting your mind wander over the question of what (at least one part of) your legacy may be. Keep adding material and looking at your brainstorm until the picture of what your legacy could be comes into focus.

It may not come immediately, but even if it takes years, keep checking in with yourself each year. By doing this – setting an intention and revisiting it over time – you will engage both the conscious and the powerful subconscious components of your mind in the service of discovering a meaningful goal or milestone to work towards moving into your mid-to-late career.

A word of caution is that, while leaving a legacy is something many people find much fulfillment in, it can also be dangerous, if we move beyond the joy of working towards an exciting impact and conflate our sense of worthiness/value with firmly achieving the legacy we envision.

Mitigate the chances of becoming unhealthily attached to achieving your legacy rather than working towards it by practice the art of mindfulness, reading idea #8, and focusing on enjoying the journey that the path of creating your legacy leads you on, rather than the outcome.

5: Work for a product team or a services company

As the saying goes, there are two types of X in the world.

In business, there are (commonly) 2 types of models: the companies that produce a product (whether a physical product like Nike or a digital product like Netflix), and the companies that offer a service (such as Accenture, or the ad agency, Dentsu). 

We all begin our careers in one or the other type of company, and often we find ourselves either moving up through the ranks within that same company, or in a new company with the same business model. While companies of one type often end up creating a team or business unit of the other type (i.e. a services team within a product company, and vice versa) the cultural DNA of a company that grew up earning its revenues from a product is generally different from one that grew up earning its revenues from services.

There are pros to being in a services company, and cons, and pros to being in a product company, and cons. There is no one type of company that is “better,” so one of the best things you can do is to experience what it’s like to work for both types of companies.

6: Design your own job. Then do it.

Take what you understand about the needs of your organization, your skillsets, what you enjoy doing, and what you want to learn next, and turn it into a job description. Then, figure out how you can start doing that job.

This isn’t an exercise I would recommend trying to fully complete by yourself. We all have blind spots, knowledge gaps, biases and harmful narratives or self criticisms, any or all of which can get in the way of this exercise. Consider enlisting the help of your manager or someone else to help you brainstorm, bring it all together, refine your plan, and make it happen (see idea #10).

If there’s no possible way for you to design your own job right now, then try it anyway for the fun of it, and to keep it in mind (and redesign it) over the years! You can even examine afterwards whether any elements of your dream job might be possible to try out on a future project.

7: Take time off from work or explore a < 40 hour workweek

We are lucky enough to be entering a new age of work where the stigma of taking a significant length of time off before official retirement is fading away. Many companies offer and even encourage sabbaticals, and hiring managers have also come to appreciate, understand, if not value the courage to take time off to enjoy our lives beyond work and recharge. 

Additionally, more and more countries and organizations are offering < 40 hour workweeks.

So take advantage! Round out your career by exploring a different style of working or taking time off every so often before getting to the end of your career. You may find that you have fewer regrets and are more fulfilled by your late career.

8: Explore what is meaningful outside of work

At the end of the day, work shouldn’t be everything and your only focus. Burnout is a real and serious risk from over-attachment to work, and so it’s essential to your wellbeing to round out your life beyond work, too.

One mistake people make is to apply a work mindset to their pursuits outside of work, by assuming that anything they do needs to be productive, or generate an income. This is not true. 

Beyond developing and maintaining your family and relationships, take time to explore different hobbies and pursuits. Find outlets that enable you to tap your creative side, or feed your desire for learning, or fuel your need for connection and belonging. If you’re having challenges thinking of what else you could do, here is a list of 50 ideas.

9: Conduct a personality assessment

Know thyself better.

If you’ve never explored and reflected on your values, your personality structure, or the way that you operate, then this is definitely one easy foundational item to do. Try taking the Meyers Briggs test, the Enneagram survey, the Via Character assessment, the Big Five test, or a values survey.

This can also empower your mentor coach to support you better (idea #10).

10: Work with a mentor or coach

Learning to ask for help, to rely on others, and to not try to do it all by ourselves is a sign of maturity and is key in the process of charting your career. While we may want to be self sufficient early-on or to help others without looking for the same for ourselves, the wisdom of experience grants the ability to see the truth that we benefit greatly from the perspectives of engaged others who care about us.

Participate in mentoring opportunities in your organization, tap your network for mentors, or consider working with a career coach to help you see the big picture, set goals, and make decisions, and is an invaluable part of enabling you to enjoy a well-rounded career.

That’s all for today! Stay tuned to The Musing Mind for more leadership takeaways and sign up for newsletter to get more career advice and inspiration delivered regularly.

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