Discovering a New Career Path: A 21-Day Journey

new-career-day-1Some people know at an early age what they want to do and be in life. They proclaim it, they pursue and the right career path just opens up.

But what about the rest of us?

What if you are still not sure where your true passion and purpose lies? What about when you pursued your “dream career” only to find out that you really hated it?

Now you work, you make a living, but you are really spinning your wheels. Now what?

Being able to do what you love and love what you do is great combination, but it seems like most of us don’t get there fast enough.

I hear you and I understand.

So before we say goodbye to 2016, join me on a 21-day, soul searching journey.

Learn key strategies that can help you discover a new career path, do what you love and actually build a life from it.

So how does it work? Every day for the next 21 days, I will offer a recommendation, suggest a task and give you an assignment to bring you closer to that dream job/career.

Your mission, should you choose to accept it, is to be open, pay attention to what comes to the surface for you and make a commitment to see the process to the end.

I promise that you will learn more about yourself, get a better understanding of careers that appeal to your passion and hopefully get the courage to move in the right direction.

So are you onboard? Still skeptical? That’s okay. Join me anyway, you may be surprised by what you’ll discover along the way.

Get a journal and a quiet space and let’s get started…

Day 1: If money, or time, or current responsibilities were not an issue, what would you like to do with your life, more than anything else in the world?   

Drown out the “what ifs” and “I am not being realistic” or “I am too old to do that” and other nagging doubts before you answer that question.

Hint: Think about your childhood and the activities you enjoyed.


Day 2: Take a close look at your answer from yesterday. What did you find out? What activities and tasks can you identify that give you the most pleasure?

Use the following list as a starting point, but really get introspective…this is about you and your interests.

  • organize things
  • build things
  • sell things
  • train people
  • help people solve problems
  • work on science projects
  • figure out how things work
  • play instruments
  • work with numbers or charts
  • analyze situations or trends
  • work on science projects
  • learn about other cultures
  • influence people
  • do experiments

Hint: You may be already tapping into your interests through hobbies or volunteer work.


Day 3: By now, you should have narrowed down what you would like to do more than anything else and made a list of your interests. So, what would a perfect work day be like for you?

Hint: Take your top 5 interests and imagine using them together in a job. Dream freely, this is part of the exploration process.


Day 4: Take a skills inventory and interest assessment tool to start narrowing down some new careers you can explore over the next few months.

You can have so many interests and likes that it’s hard to see how they can come together in an ideal career.

Hint: You have both free and low-fee choices for taking the assessment. Check the assessment out at Interest Profiler at O*Net or iStartStrong assessment at


Day 5: Connect with a career coach, a mentor, trusted colleague or to review your Skills and Interest report. (See sample)

Have that person review the highlights of the report with you and pull out the top 5 vocational / career groups that stand out for you immediately.

Talk through and discuss the following questions without judgment or skepticism:

  • What are you naturally motivated to do?
  • What kind of work you naturally do well?
  • What is most important in work and life for you right now?

Hint: Pay attention to your gut reactions as you review the list. You will definitely see old career goals/ dream jobs (that you abandoned) reappear here.


Day 6: Take a day off and digest everything you have done over the past 5 days…you have done a lot!

Making the decision to move in a new direction starts with the right mindset; having the commitment to actually taking the steps and doing the research takes courage.

Hint: The range of emotions and trace of nagging doubts you may be feeling now is normal. Stepping outside your comfort zone at any stage of your career is not easy.


Day 7: Go back to the Skills and Interest report and make a short list of careers / job titles that you want to research further.

Don’t make any sudden career changes/moves right now as you’re still in the exploration phase. However, it is very important that you keep taking action and moving forward.

Hint: You know someone, personally or professionally, who works in one of the new careers you are evaluating at this time, but we’ll cover that later on.


Day 8: Celebrate, you are one-third way through this journey. At this point, you should have a short list of new career paths to explore for the next 2 weeks.

No pressure to make a decision right now, but also resist the urge to turn back or giving up at this point. Forget about your background, experience, training or even age.

You are not leaving your job or giving up what you know, you are simply exploring the possibilities. Now it’s time to find out first hand what those careers are really about.

For every new career you see as a possible match for you, find someone in your personal and professional network who is doing it. Ask around and get introductions.

Hint: Your network is not just limited to the people you know directly; each person in your network, has a network. You are connected to more people than you think.


Day 9: Continue building your list of contacts and expanding your professional network that aligns with your new, possible career paths.

Have you ever heard of the red car effect? It’s not until you go looking to buy a red car that all of a sudden, it seems like everyone on the road is riding a red car.

Hint: Talk to colleagues, friends, family members, past clients, sorority / fraternity associates, college alumni, you have great connections right under your nose.


Day 10: Start scheduling your informational interviews, informal meetings and coffee chats with people who can give you insight into new careers.

Get it straight from a reliable source. Be sure to ask them about their career journey, find out if they are career changers, get their perspective on why that career is a good choice.

Hint: People LOVE sharing information a lot more than you think…it’s also a great opportunity for your contact to reflect on his/her career journey.


Day 11 to Day 16: Use powerful questions in your informational interviews, maximize this vital opportunity to get golden nuggets of industry/career data.

Now sure where to begin? Here are a sample of good questions to ask:

  • How did you decide on this career?
  • What skills, education, and experience are needed to enter this field?
  • What skills are needed most for these type of job?
  • What is the hiring process like at your organization?
  • What type of individual usually succeeds in this career?
  • What are the rewards/challenges/frustrations of your work?
  • What do you wish you would have known prior to entering this field?
  • How does your job affect your general lifestyle?
  • What would you change about your job if you could?
  • Where do you see yourself going from here?
  • What are the new developments in the field that you think are important?

Hint: Remember to build new relationships as new contacts can quickly into allies, advocates and referrals when you select a new career path and launch a job search.


Day 17: Reassess, reflect and review the mountain of information, insights and advice you have gotten in the 16 days.

First of take another break and digest all that info. At this point, you have successfully moved beyond your comfort zone and taken serious action to find a new career path.

More than just thinking about it, you have explored it deeply and connected with other professionals who are working in those careers now. Are you really going to turn back?

Hint: It’s going to be hard to go back to the “same old, same old” now. You have seen what’s possible, talked to others who have made it happen. Don’t stop now.

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