STEP NO. 1 | Hindsighting


Welcome to Step No. 1 of the Guide to Career Pivoting For Entrepreneurial Types.

To get clarity on your entrepreneurial career pivot, it’s best to start by uncovering clues from your past professional and personal experiences.

Let’s kick-off the hindsighting process…

NOTE: If you’d like to type out your answers, here’s a link to the Google Doc with all the questions. Simply open the link, click “File,” and select “Make a copy” or "Download as."

First, let’s get a broad overview of your career history:

How did you come to be here in your life?
Reflect on how you got to be where you are today, what choices did you make? Why? Which ones still align with who you are today?

What have you achieved to date?
Reflect on your past accomplishments. What are you most proud of?

 Next, let’s take a look at how you spend your resources:

How do you spend your time?
Review your to-do list, your calendar, and your current commitments. For this one, you’ll want to look at the past year as well as what you have coming up.

How do you spend your money?
Review your bank, Paypal, and Venmo account. Thoroughly analyze your spending habits for the year.

Now, let’s find out what’s not working, this will likely be easy to come up with:

When do you feel drained?
Looking at both your work and personal life, what things do you dread and avoid doing?
    What or who makes you feel angry or frustrated?
    What do ruminate about, or who do you vent about? What specifically irks you about those scenarios or people?
      What do you feel is unjust?
      This may be something you believe is personally or professionally wrong or unfair. It could also be a broader social issue you want to rectify.

        Then, let’s tackle what is working. This is often more challenging but will be even more meaningful to uncovering your next pivot.

        What are you distinctly good at?
        Identify your inherent signature strengths along with the skills you’ve acquired through work and personal life. Don’t just list adjectives, get specific.

        What do people come to you for advice on?
        This gives you an objective perspective on your strengths and skills.
          What activities get you into flow?
          Identify the work and personal activities you naturally gravitate to, the ones that energize and engage you, the ones you find yourself getting lost in.
            What do you enjoy talking about, listening to, watching or reading?
            Identify the topics you’re innately curious about. It’s helpful to observe when you light up in a conversation, what articles you click on, the podcasts you listen to, the videos you watch, your browser history, your recent book purchases etc.
              What are your quirks?
              What makes you, you? What are your unique traits and/or habits people typically associate with you or remember about you?

              Finally, let’s get to know your preferences and tendencies.

              For some answers, you may be somewhere in between. If so, include specifics around the scenario. And when relevant, include percentages to indicate where you are on the spectrum.

              What’s your preferred work environment?
              Home, coffee shop, open coworking space, private office, tropical island etc. Get as specific as you can regarding location, people, noise levels, and design elements.
                What’s your preferred communication style?
                Writing, one-on-one conversations, group discussions, public speaking, teaching, performing etc. This can be a combination of what you enjoy, and what you’re best at.
                  Do you prefer predictability or spontaneity?
                  Do prefer having a plan or keeping your options open? Which one do you find less stressful to cope with?
                    Do you tend to be more introverted or extroverted?
                    Do you tend to get more energized by solitary activities or social interaction? This is less about whether you are shy or outgoing.
                      Do you tend to be more interested in ideas or facts?
                      When coming to a conclusion about something, do you look for theories and deeper meanings or do you look for data? We all use both, but which one is more important to you, or simply more enjoyable for you to dissect?
                        Do you tend to make decisions based on logic or emotions?
                        When dealing with people, do you care more about coming to the practical solution, or coming to a consensus?
                          Do you tend to respond to inner or outer expectations? Neither or both?
                          Are you more likely to complete something if you believe in it or if someone is counting on you to get it done?

                          Now, let’s move onto Step No. 2…