20 Unconventional Tips to Reboot Your Career
Ideas and reflection questions to help you figure out what’s next
Are you feeling stuck in your career? Are you ready to make a change and try something new? If so, you’re not alone. Many of us at one time or another have wanted to make a change or start fresh in our careers. Having the right strategies and resources can help make the transition smoother and more successful. From taking on a challenging project and getting more organized, to finding a mentor, these tips will help you find more leverage in your career.
- The surest way to find work you love doing is to believe you are worthy of a career that you love. Every seed has the innate ability to sprout, given the right conditions.
What conditions do you need right now to really bloom?
2. Don’t confuse finding a job you love for one that will always make you happy. I love my partner more than words can describe, but he doesn’t always make me “happy.” I love summer, but sometimes the heat is uncomfortable and I’m overwhelmed by how much I want to experience in a season that always seems too short. I love mac & cheese, but I couldn’t eat it every day without getting sick of it (and making myself sick in the process).
What is one thing that will help you really **love** a job?
3. I firmly believe we are all creative beings. Literally born to “create.” A job that doesn’t leave room for turning nothing into something is likely to feel soul-sucking real quick, no matter how great the pay, the team, or the mission.
What is one way you can be “creative” at work?
4. The more narrow your job search goals, the easier it is for people in your network to help you. When a friend tells me they want a better job, I nod and wish them luck. When they tell me they’re looking for a product management role at an early stage prop-tech company in New York, I make some introductions.
What is one new filter you can add to your next job search?
5. Remind yourself that even the people who most impress you don’t have it all figured out: they have just found a lane that leans into their natural talents and genuine interests. There is probably something about you that others admire or find intimidating. Find out what that is and then look for a career path that presents the most opportunities for you to leverage those things that come naturally to you.
What do others admire about you?
6. You will drive yourself crazy if you search for the “perfect” career. There is no such thing as the “one” job or company or profession for you. There are many paths that can fulfill you.
What are all the paths you have taken so far that brought you joy?
7. If you’re at a crossroads and not sure which path to take, try to choose the one that is least likely to lead to a dead-end. Optimize for growth and watch how much everything else will fall into place.
What is *one* thing I can do today to ensure I am growing?
8. As humans, we have evolved to have at least some variety in our lives. As soon as a path is starting to feel too familiar and predictable, it’s time to recognize that you are on a treadmill and not a path. Time to jump off and go outside for some inspiration.
Do you need to change your whole career or just need some more inspiration and variety in your life?
9. If you’re feeling stuck, even one small step, in any direction, is better than no step. Don’t worry about updating your resume, just update your LinkedIn headline. Message a friend and tell them you’re thinking about quitting your job. Set a google alert about a company you love. That’s enough to get the ball rolling and start building your confidence that something better is possible.
What is one small step you can take today to help you find more meaning in your career?
10. If you’re really not sure what you want to do next, ask yourself first what you want to learn.
What do you want to learn?
11. Take time to reflect on lessons you have learned from your current “career.” Try to create a list (like this) of the top 10 or 20 lessons. Push yourself to state the obvious. Ever notice how some of the most prolific and well known thought leaders are just stating what everyone else is thinking or feeling? Adam Grant, Deepak Chopra, James Clear etc…aren’t famous because they have invented something new or discovered something complex, but rather because they communicate something old and basic. They communicate really obvious and universal truths in a very clear and concise way.
What is one thing about your current job that others should know about?
12. Reflect on what truths about you might be hiding in plain sight by reading old journals, looking at old photos, considering what books or movies you are drawn to. As they say “pay attention to what you pay attention to.”
Is there a topic in books or shows or articles that always draws you in? What deeper truth might that reveal about you?
13. Sometimes we create distance between ourselves and what we fear. Perhaps the single best thing you can do for your happiness is to see yourself as equal to everything (and everyone) else in nature. Bringing this attitude to your daily life will allow you to build deeper with your team members and as you network, and perhaps even open your mind to fulfilling career paths you previously thought beneath you.
What (or who) do you think you are “better than?” Why? What does this say about you?
14. The concept of “guilty pleasure” should be banished (assuming we’re defining guilty pleasures as something like taking a nap during a workday or watching Office reruns and not something that would bring harm onto others or the planet). We have one life to live, why deny ourselves of simple pleasures?
What is one thing you enjoy but feel guilty about? Is that guilt necessary?
15. If you’re feeling indecisive, take some pressure off the decisions you are trying to make and remember that virtually any decision you make can be undone. You can quit a job you aren’t enjoying, move back to where you came from, apologize for a mistake etc.
Is there something you’re currently worried about that is holding you back?
16. If you zoom out far enough, there are no wrong decisions or paths. The more you can take the perspective of a 500 year old tree or an alien looking down observing humans, the more you will see that all that matters is that you approach everything in life with a sense of wonder.
What would 75-year-old you advise right now?
17. We all have chapters to our lives. What was right for you at 16 is not necessarily going to be right for you at 36. Sometimes it makes to stay in a boring corporate job to take advantage of the benefits or save enough money to quit without worrying about how the bills will get paid. Other times it will make sense for you to work at an early-stage startup where you can work more cross-functionally until you’re ready to strike out on your own and have more control over your schedule.
What type of work does this chapter of your life call for?
18. There are so many more “jobs” out there than you realize (and way way more than we were raised to believe exist). Depending on the industry, you can be anything from a workplace connections expert to an augmented reality designer, a behavioral coach, a wedding singer and so on. Don’t limit yourself to just the jobs and titles you are familiar with.
What new job titles or roles can you come up with that might be perfect for you? If you could create your *ideal* role, what would the job title be?
19 .You don’t need to justify the things in your past that you are insecure about. A winding unconventional path is totally valid. What’s important is to figure out what you learned from each of your experience to help inform what you do next.
Is there a better way you can frame something you have previously felt the need to defend?
20. The best jobs are not found on the internet, and are not offered to cold resume submissions. Network, network, network. Don’t give up.
Who is one person you can reach out to today who would be willing to introduce you to someone new?
No matter what our career paths look like, they are all valid. Rather than feeling stuck on a treadmill, take small steps to move forward and get inspired. Reflect on lessons you have learned in the past, consider what you want to learn, and determine the type of work this chapter of your life calls for. Take it one step at a time, don’t be afraid to network, and never underestimate the power of simple pleasure. With this attitude, I can almost guarantee you will find your place, find fulfillment, and create a career that is meaningful and satisfying.
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