Are You Ready to Take the Entrepreneurial Plunge?

When a creative decides to strike out on their own, whether they realize it or not, they enter into the world of entrepreneurship. While becoming a freelancer may not seem like a huge risk, all business ventures involve risks at one level or the other. And risks, of necessity, assume the possibility of failure.

Not everyone is cut out for entrepreneurship, even if it’s just a solo creative practice. Taking responsibility, not only for doing the work, but also for getting the work, billing the work, paying taxes, managing an LLC, marketing, and more, can feel overwhelming—especially when you’re just getting started. It’s always wise to count the cost of entering into business and to sober-mindedly reflect on all these responsibilities. But even after you take stock, underneath there still lurks the basic, and real, fear that you might fail.

Can You Face the Fear of Failure?

One of the key tests for whether or not you’re cut out for entrepreneurship is simply your ability to face this fear, accept it, and reconcile yourself to that very real possibility that it could happen. If you’re contemplating such a decision, or perhaps reconsidering one you’ve already made, take a minute and put these fears into proper perspective. What’s the worst that can happen?

Creative Entrepreneur is Not Brain Surgery

Whenever I get stressed, when the road of creative entrepreneurship gets bumpy, I remind myself that while there are serious matters involved, the very worst outcome is not even close to life and death. If I design a crappy website, nobody dies. There are career choices that have far more serious consequences. If a surgeon fails, someone’s life really is at stake. I don’t want to be anywhere near an airline pilot if there’s going to be a worst-case failure in the air.

So while entering into business is serious, we really shouldn’t be paralyzed by fear in the face of potential failure. I suppose the worst-case scenario, for a creative business, would be that you simply go out of business. Now if you unwisely accumulated debt in the process, and you didn’t form an LLC, or if you personally guaranteed debt, then you might have some more serious personal financial problems as a result. But even then, the worst case might be personal bankruptcy. No one wants to face that possibility, but it does happen all the time, and you can recover. I’d highly recommend avoiding debt altogether. If you follow that one simple rule, then the worst case of going out of business just means that you’d have to look for a new job (or start a new business). That can take time and be stressful, but still, we’re not talking smoldering crater.

Resize Your Worst Case Scenario

I’m not one to obsess over worst-case scenarios, but it can be helpful to realistically think through some of them as you contemplate entrepreneurial choices. You need to put real risks into proper perspective.

In the decision-making process, there’s a fine line between careful planning with thoughtful assessments, and letting paralyzing fear cause an inability to make a decision. I’ve seen creatives fail simply due to being either too nonchalant or too anxious in the decision-making process itself. Hastily made and poorly thought-through plans can result in failure. But being too tentative can also cause you to fail. Striking a balance between the two is perhaps one of the biggest keys to success in entrepreneurship.

A Short List to Contemplate

Here’s a list of things to work through as you contemplate, or reconsider, your entrepreneurial choices. If you can work through them realistically, without getting too caught up on any particular matter, then you might be prepared to make this leap.

  1. Do you have financial resources (either in cash savings or sustainably low expenses) to give yourself time to get off the ground? (Three to six months would be a good benchmark.)
  2. Can you invest extra time resources for a season to get up and running? (You may need 50 hours per week or more, for a time.)
  3. Do you feel comfortable making (and keeping!) a budget, and planning your schedule?
  4. Do you have a strong point of view, robust connections in an industry, or a specific area of expertise that you can leverage for early-stage marketing?
  5. Can you temper your inner perfectionist in order to build a brand for yourself (including name, logo, website, and initial content) that you don’t have to spend over 100 hours on?
  6. Are you comfortable with the processes of setting up bank accounts, talking to an attorney, and working with an accountant? Or are all the technical matters of LLC formation, self-employment tax, website creation, etc., entirely new to you?

This is not a comprehensive list (if you’d like a more thorough assessment take my Freelance Suitability Survey). If this brief list is already making you feel overwhelmed, maybe this is not the path for you. But if you aren’t put off by these considerations, you might be ready to take the plunge—after all, what do you have to lose?

Are you ready to take the struggle out of finding new clients?