A word of caution as we begin tackling Is self-employment a good fit for you? from a few different angles…

Exercises like this are riddled with confirmation bias—i.e. when asked a set of binary self-assessment questions, a respondent will consciously or subconsciously select whatever answer they believe will aggregate toward the conclusion they wish to hear.

So, rather than thinking of this as an assessment, take these questions as a gentle guide for slow, honest reflection.

Then use that reflection to draw your own conclusions on your natural aptitude for self-employment.

Angle #1: Motivation

The move from corporate to self-employment can be jarring, even if you’ve worked towards it for some time.

Corporate workplace norms and habits become so deeply ingrained that it’s difficult to imagine a different way of operating.

For example:

• In corporate, you have a direct manager.
  What would your days look like if you didn’t?
• In corporate, you work towards promotion.
  What if there were no promotions (title or salary), just ongoing work?
• In corporate, you work in service of a broader strategy.
  What if there were no established mission or timing expectations?

Needless to say, self-employment as an independent consultant or other soloist requires a heightened self-starter mentality—one that is able to prioritize progress (big & small steps) without external prompts or oversight.

So the question for this first angle is: Are you a self-starter?

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To gauge this for yourself, consider the following:

Professional behavior:

• In corporate or volunteer groups, do you gravitate toward leadership positions or prefer to be led?
• On teams, do you tend to be a doer or a delegator?
• Can you manage your own time/priorities proactively and consistently?
• Does your excitement about projects sustain as the work continues, or does it wane quickly after kickoff?
• Can you complete non-core or administrative tasks without external oversight or deadlines?

Personal behavior:

• What have your days looked like during periods of unemployment, job search, or career break? Were they structured? Unstructured?
• Have you ever tried to intentionally introduce healthy habits, or break unhealthy habits/addictions? Were you successful?
• Are there examples in your life where you’ve taken a bold, self-motivated action? (e.g., cross-country or international move, marathons or other physical challenges, ending a long-term relationship/marriage)

Broad reflection:

• Are you an intrinsically or extrinsically motivated person?

Take your time - these are deep questions about what prompts you to action.

Thinking through them honestly should provide a directional answer to whether a self-starter mentality is an existing trait of yours or one you can work on.

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The second angle tomorrow…

💡

-Wes