Let’s Talk About Failure

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As an entrepreneur you spend a lot of time looking towards the future. Thinking big. Taking calculated risks. Planning for expansion. But what if you … fail?

Failure is inevitable in any business. Some failures are small—losing a bid to a competitor or a bad experience with a new customer. Some failures are monumental—not being able to make payroll or being unable to get your product across the finish line. Many small business people refuse to think about failure, fearing it might manifest itself. But the truth is, thinking about failure can be a valuable exercise and keep small stumbles from becoming tumbles off a cliff.

So let’s talk about the do’s and don’ts of failing. (Set your superstitions aside. We promise this will be helpful and not at all a bad omen!)

Make like Scar

Yes he’s the villain of Lion King, but when Scar sings Be Prepared he’s making a pretty logical point. (Even villains are right sometimes.) Large organizations often spend time creating contingency plans around natural emergencies such as severely impactful weather, as well as man-made emergencies such as supply chain issues or financial misappropriation. If you’re a Solo Hustler, you don’t need to spend a lot of time protecting yourself from the liabilities of a large staff. But you should put plans in place for the kinds of unexpected disasters that can happen.

Establish a support network

The biggest threat to being a solo-preneur is the lack of backup. Your customers are counting on you to meet deadlines and expectations. Your livelihood relies on that as well. So what happens if you’re ill or have a family emergency?

Find people in your field who can cover for you if needed. Maybe you and another photographer are each other’s backup for weekend shoots. Join a local organization in your industry to find additional resources. Start building a contact list of subcontractors to both increase the workload you can manage and have people to fill in when you are unable.

Expand your portfolio

The documentary Beanie Mania follows the rise and fall of the Beanie Baby phenomena, including the outcomes for all the people who built side businesses appraising or cataloging the toys. When the world moved on from its fascination with small bean stuffed animals, most of these businesses dried up overnight. Take a long look at your side hustle and consider whether everything relies on a single source of inspiration:

  • Check out your competitors and see what additional services they are offering.
  • Look at the skills of your subcontractors and determine if you can add additional services.
  • Make sure your resources are not sourced from a single vendor, leaving you in the lurch if they have problems with their business.
  • Talk to your best customers about the value they find in your businesses and what other services they might need.

Learn, don’t linger

So you failed. You lost the bid, you lost a customer, or you just didn’t make enough money this month to keep from raiding your savings. Get over it.

OK yes, that was harsh, but as a Solo Hustler you can’t afford to just sit back and stew. And sometimes a small step back can be the catalyst for a large leap forward.

  1. Analyze what went wrong. Was the pitch different than usual? Were you outside your comfort zone? Were you up against a competitor offering something better than you?
  2. Write down your mistakes. Being candid with yourself is an empowering activity. Acknowledge what you did wrong from the small (too many typos) to the large (total misunderstanding of what the customer was looking for) and be brutally honest.
  3. Come up with a game plan. For each mistake, make a plan for how to fix or avoid it in the future.
  4. Look at past mistakes. Sometimes it takes a few failures to finally spot a pattern. Preserve these exercises and refer to them periodically. Watch for patterns. Maybe you always lose deals at the end of the month when you are preoccupied with other business requirements. Move your pitches out a week and see what happens.

Don’t give up

Most importantly, don’t assume that one mistake means the end of your business. Your drive, ambition, and self-confidence got you this far. Dust off and keep going.


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