Roadmap to Self-Employment: What is Your Why and Who?

So you’ve determined that you want to be self-employed and that you’re cut out for the entrepreneurial journey. Now what?

The decision to be your own boss can come with a big rush.  Like a YORK Peppermint Patties commercial of the days gone by.  That’s fine for a while (like maybe an evening of some fine cocktails), but then what do you do?  This is where business planning comes in.

Take heed of the well-worn quote:

“She who fails to plan, plans to fail.”

That said, you don’t’ want to fall into planning paralysis either.  I’ll talk more about business planning and whether or not you need a business plan in the next installment in this series. For now, let’s focus on the big picture WHY.

A few very important questions to ask yourself:

  • Why do I want to be in business for myself?
  • What positive impact do I want to have on others?
  • Who do I want to serve?
  • In what way do I want to serve them (i.e., what is your product or service?)?
  • Who am I and what do I stand for as a person?

It can look tidy to line these questions up in a bulleted list like something you can knock off your to-do list before lunch, but these questions require some serious introspection.

In the book “Start with Why”, Simon Sinek says:

“There is one missing detail: WHY: Very few people or companies can clearly articulate WHY they do WHAT they do. When I say WHY, I don’t mean to make money – that’s a result. By WHY I mean what is your purpose, cause, or belief. WHY does your company exist? WHY do you get out of bed every morning? And WHY should anyone care?”

Most traditional companies (whether a sole proprietor or a large corporation) start with getting bogged down in the details of what they will offer and how they will offer it. These are important but unless they are fueled from the inside you will fail or at best limp along at the back of the pack.  Your WHY and your own uniqueness IS your differentiator.  It is your brand. If you are a solopreneur you and your brand are synonymous.  (If you want to dig deeper into why this is so, I talk at length about your own uniqueness as a key success factor in the new world of business in my free white paper.)

  • So what difference do you want to make in the world?
  • Who are you, really when you get to the core of your authentic self?
  • Why do you want to do this in the first place? Is it because you want to live out your true calling through your work in the world? Or, are there other driving factors?

These all lead to your WHY.

What is Your Business Why?
Credit Image: photosteve101 via Flickr

As you go through this inner inquiry, inevitably you stumble across the next question that is the WHO.  Who do you want to serve? Who do you want to work with? Who is your ideal client?  Some questions to consider when it comes to ideal client:

  • What makes them tick?
  • What is their problem that you solve? What are their pain points?
  • What values do they have? What matters to them personally and professionally?
  • What are their deepest desires? What do they want that they don’t have now?
  • What are these people like? (The qualities of your ideal client are especially important for service based businesses because you will likely be working directly with them. So, do you want them to have a sense of humor? Be fun? Spiritually oriented?)

Much like with the first set of questions…there is no such thing as a wrong answer here.  I repeat – there are no wrong answers!  At this stage of the game you’re talking vision and your personal and business purpose.  Viability and business model will come later. For now, wave your magic wand and focus on what wants to emerge for you.

In case you’re feeling like this is too fluffy or you don’t have time for this type of reflection (because you need to get that business up and running, right?), here’s why you need to give yourself permission to do this from your heart and what you really want.  If you only undertake this exercise from this head I guarantee you that you will create one of the following:

  • A business that is financially successful that you hate even more than the job you just left.
  • A business that fails and can’t move forward because you’re just not that into it. You’re going through the motions because it is what you thought would make sense instead of what would make you (and your customers) come alive.

Believe me – it takes courage to be authentic and commit to creating what you want instead of what you think you should want.  As a recovering intellectual who wanted to make everyone else proud (even at the expense of my own happiness) I created my own little hell when I first started my business because I drove immediately down the road of “should”.  What should I do? Who should I work with? What would make the most logical sense?  I created nothing but emotional and practical roadblocks for myself because I wasn’t aligned with what I was trying to create.

I want you to avoid this painful path. That is why I write and work, present, and coach people on this very thing.  The life plan always comes before and must be integrated with your business planning; anything less than that is a half-lived life and a recipe for failure.

Take some time to reflect upon these questions. Whether you are starting up your business or have already been in the game for a while, you can always benefit from this reflection.  Being an entrepreneur is about ongoing reinvention and these questions are where it starts.

This post originally appeared on

Scroll to Top