STEP NO. 2 | Insighting


Welcome to Step No. 2 of the Guide to Career Pivoting For Entrepreneurial Types.


In addition to observing the past for hindsights, it’s critical to look within to uncover insights.

Often, we don’t take the time to understand ourselves. This lack of self-knowledge is why we find ourselves on career paths that aren’t a fit.

This insighting process will help you better understand that ever elusive subject: yourself.

The following questions will require you to get raw and vulnerable. What you find may be illuminating.

First, let’s start with your self-image:

What do you like about yourself?
This tends to be something you positively identify with, often, something you’re known for within your close-knit circle of friends/family.

What are you self-conscious about?
This could be related to your social or financial status, and/or a physical or personality trait.

What’s one thing you would change about yourself if you could?
We are all enough exactly as we are, and don’t need to be fixed. The goal of this question is to understand what you perceive as your most significant flaw.

What’s a common misconception about you?
This is a false assumption people make about you based on split judgments or when they haven’t had a chance to get to know you.

What do you wish people knew about you?
This is something that you know is true about you but it is not widely known.

Next, let’s get to know your aspirations and challenges.

Is there someone you would trade careers with?
Whose career do you admire? Who is doing something that you'd like to be doing one year from now? These people are often a mirror reflecting back what you want. 

Who do you want to connect with?
Who are you fascinated by?  Who do you want to learn from?  Who would you like to build a relationship with? What community would you like to be a part of?

What's your vision for your career one year from now?
What would success look like? How do you want to feel? What results will you see? What kind of impact will you make? Be bold and think outside the box.

What habits would you need to break to hit your goals?
We all have habits that can sabotage our progress. Identify the things you do that are holding you back.

What habits would you need to cultivate to hit your goals?
In addition to breaking habits, hitting your goals require you to step up and be the person you want to be. What new habits will propel you forward?

What skills would you like to improve upon or learn?
Learning and growth are essential to making your pivot and are core to career fulfillment, identify what expertise you’d like to build upon.

Aside from your career, what two other areas of your life are most challenging?
These are challenges that consistently take up mindshare. Typically they’ve persisted over the past few months or longer. It’s could be in the area of love, family, friends, health etc.

List 10 things you would do during your ideal yet realistic week.
This will give you insight into how you would spend your time if you had complete autonomy.

 Now, it's time to talk finances.

What type of work would you do for less money than you make now?
To prevent you from overvaluing money, this question helps you see what type of work you truly enjoy. Keep in mind this doesn’t mean you'll have to make less money in order to enjoy your work.

How much money do you need to make? 
Identify how much money you'll need to cover at least six months of expenses. This will help you make a pivot that supports your financial needs and doesn't send you into panic mode. 

How much money would you ideally like to make? 
Often, we come up with arbitrary money goals. Identify how much you ideally want to make and what you plan to do with this money. This helps you understand your intentions while giving you a tangible horizon to work towards.

It’s the time to codify all your answers into your core values.

All the questions you’ve answered in both the hindsighting and insighting process have led you to this exercise.

A few notes on what your core values are...

Your core values are essential. They represent your deeply held beliefs, your highest priorities. They are your north star, your guiding principles. They will serve as a manifesto for your career and your life.
    Your core values have always been there. They reflect the choices you’ve made and your desires. Likewise, when you’ve been frustrated or riled up, it’s probably because your core values were violated.
      Your core values will remain largely the same. Even when your interests and goals evolve, your core values are unlikely to change significantly. Of course, you may refine them as you foster more self-awareness.
              And what your core values are not...

              Your core values are not things you ‘should’ value. Identify what is truly important to you, not what will make you appear virtuous. Selecting ‘generosity’ or ‘aesthetics’ does not make you a better or worse person. It just makes you, you.
                Your core values are not the same as fundamental human values. For the most part, we follow the ‘golden rule’ and aspire to be loving and kind. We care deeply about our loved ones and our community. Don’t mistake these for your core values.
                  Your core values are not tangible. They are not things you can have like money or enjoy like a vacation. They are intangibles that reflect what matters most to you like growth, autonomy, impact etc.
                    Your core values are not a laundry list. If everything is a core value to you, then nothing is really a priority. A useful set of core values are ones you know inside out and can recite from memory.

                            You’re ready to define your core values!

                            List your core values.
                            Select five or fewer core values to focus on. Phrase them in question form. This allows you to:
                            • Evaluate how you are living by your core values today, and how you can further live by them.
                            • Evaluate all future decisions and opportunities moving forward.

                            Here’s an example of core values:

                            Growth
                            Am I moving forward beyond my limiting beliefs?
                            Am I exploring new ideas and experiences out of pure curiosity?

                            Autonomy
                            Am I able to decide what I’m working on?
                            Am I able to decide when and where I work?

                            Impact
                            Do I play a critical role?
                            Does this drive tangible change at scale?
                            Does this create meaningful, positive results?

                            Now, let’s move onto Step No. 3…