Six Questions to Help You Pick a Career That You'll Love

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I am currently leading 20-people through a three month “design your life” course and we started everything off by articulating our dream for 12 core areas of our lives.

I started my speaking career in highschools and colleges and this was easily one of the most frequent questions that I received. I would often recite the same answers and realized that I never took the time to write them out. So, here they are.

If you’re not sure what to do with your career (or know someone in this spot) but feel like you are ready to start exploring a change and desire more meaningful work, here are some questions to ask yourself as a starting point.

REMEMBER THIS: Before you can identify a job/career that makes sense for you, it helps to understand just who the F you are and what’s important to you…once you understand this piece, it becomes easier to identify jobs and career tracks that will fulfill on your most important criteria.

One thing I also like to qualify here is that this isn’t for everyone, some people have pretty intense responsibilities as a parent, caretaker and simply feel they need to make a living to provide for the people they care about. Some people want the comfort of an easy 9–5 so they can pursue their passions in their free time…that’s A-OK.

The questions below are really for people who value the idea of their work being an expression of who they are and vehicle for magnifying their impact in the world.

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6 questions to help you find a career that you’ll love

1. How do I want to help people? What is the shift I want to empower in people?

Ex: Homeless to housed, unsustainable to sustainable, anxious to confident, lonely to being in community, stressed to relaxed etc.

The most fulfilling thing we can do is help another human. The more clear we are on how we want to help people, the more capable we will be of accessing fulfillment in our lives.

A helpful way to think about this is often to identify where you struggled or have been most helped in your own life and to pay forward the service/knowledge that was most helpful to you.

I.e. I used to be socially anxious and now I teach people how to feel socially confident with the tools that most helped me. A tribute video changed my life and connected me to my friends so I started a company to share that experience with the world.

2. Who are the communities/people that I want to work with?

Ex. Non profits / entrepreneurs / creatives / colleges / kids etc.

Who are the people that energize me? Who are the types of people I want to spend my days around?

3. What do I want to be really good at professionally?

Ex: speaking, writing, designing, growth marketing, leadership, coaching, event production etc.

When we feel that a job is helping us to improve a skill that we intrinsically value, we will be more inclined to care about the work and perceive it as valuable.

4. What am I naturally really good at? What do I enjoy doing just for the sake of doing it?

Ex: talking to people, good aesthetic, attention to detail, cooking.

If you understand what you are naturally energized and curious in, you will exert less energy and have more bandwidth to excel at whatever you are doing.

5. Who has a job that I would want (and why)? Who is achieving the impact and income that I’d like to emulate?

Make it real, it doesn’t have to be exact…just comparable. This is one of the most important steps to making an ambiguous career dream real. Once we find a couple of people that we really respect, we can do a few things.

  • Track their career trajectory and see how they got their

  • Reach out to them and offer your support…find a mentor

As I write this, there is literally a young entrepreneur who volunteered a week of her summer to come and help my wife Miki ( with social media strategy just to establish a relationship.

6. The big one, legacy. What do you want to be remembered for? What type of impact do you want people to associate you with after you’re gone?

This one will cut right to the core of what is important to you.

If you don’t have an answer for any of these…GREAT. This is where you should be spending your time and talking to other people. I don’t know should not be your cue to move on, it should be internalized as a marker to SLOW DOWN and pay attention.

Start asking everyone you know (especially successful people) how they discovered what they wanted to do with their lives.

Stop asking yourself, what career should I pursue and start asking yourself…who the F am I and what do I care about? Once you are more clear on that, your career trajectory will become more clear.

What else has been helpful for those of you who have been able to find a career/job that you really care about?


andrew horn