Be Your Business: Don’t Forget to Fail Well

Photo Credit - Chuck Olsen CC-BY-NC-SA 2.0

Photo Credit – Chuck Olsen CC-BY-NC-SA 2.0

Adversity: The New Normal

It happens. Things go south and it’s not even clear how. Your client and you can’t see eye to eye, or your enthusiastic new business partner has dropped off the radar. The project you’ve invested weeks, months, or years into may never see the light of day.

Failure comes in many forms and the increasing complexity of our projects and the world they operate in doesn’t help. Despite our best efforts, learning the hard way is often the only way. Perhaps this is why modern startup culture has rallied around the mantra: “Fail fast. Fail early. Fail often.” But I spent the better part of my career failing, and the experience leads me to believe the common refrain to be lacking.

Like gymnasts who train to fall properly, I believe we must learn to fail well. Something I never did. It took me 12 years and spectacular failure as a freelancer and as a startup CEO, but I think I’m starting to learn the art of failing well.

Don’t Make Things Worse

Here’s the framework I use. I hope it helps you remain lucid in the face of failure and, FSM willing, makes your next failure a little less painful.

  • Managing Yourself: Stay calm. There are plenty of fish in the sea. Mindfulness meditation, hikes, and frequent visits to the beach helped me through my most challenging failures. We can easily be our worst when things get rough, so proactive self-care is fundamental to failing well.
  • Managing the Relationship: Failure tests relationships with coworkers and with clients. Do not seek blame – most failures are collaborative – but do a post mortem. Your goal is first to establish a conciliatory, productive, tone, and only then dive into the nitty gritty of resolution. Be generous. Learn to apologize well. And, when appropriate, cut your losses.
  • Managing Your Reputation: Do not bad mouth former clients and coworkers. Learn to tell your story without peppering them with mitigating factors – they sound a lot like excuses. But actions speak louder than words, so focus on doing good and learning from the failure.

Those should help you think through your next rebound. But I’d be remiss if I left you with advice only in the abstract. I have stories and practical applications of the above framework in depth, and I’m happy to share my wisdom.

Upgrade to Better Failures

I will close with my list of the top 10 freelance pitfalls. Do your best to avoid these, or at least learn from them!

  1. Fail to Measure: Do not put this off. Do not believe the voice in your head, you should be measuring even if you don’t “have to.” Track your time. Watch your cash flow. Without data, both your business and your welfare is subject to the winds of intuition. With data, you can build ever more precise estimates and craft ever more lucrative proposals.
  2. Work Without a Contract: I don’t care if you are BFFs or married to your client, you need a contract. Even if money is not changing hands, a contract brings clarity to critical issues like ownership of intellectual property, communication standards, and warranty/maintenance. Don’t want to pay an attorney? Look online for templates, or just write a “Memorandum of Understanding” in plain English and have both parties sign it.
  3. Over Commit: It seems obvious but we humans are skilled at overestimating our own abilities, so it bears repeating. Of note, it is shockingly easy to over commit if you have failed to measure and do not know either your capacity or the current utilization of that capacity.
  4. Give it Away for Free: Pro bono work is good. But ask for a recommendation, referrals, or a case study. Even if your invoice shows a 100% discount, send that invoice. And if you’re doing a free consultation, remember you’re there to build a rapport, not to instruct your lead on how to provide the service you are offering.
  5. Surprise a Client: I’m not talking about flowers or wine here. I’m talking about failing to set expectations, or over promising then under delivering. People are more forgiving than you think, so alert them at the first sign of danger. Nothing is worse than radio silence.
  6. Do Everything: Don’t be everything to everyone. Even generalists need a specific hook. Consider subcontracting for things that aren’t central to what you offer. For instance, don’t do your own taxes just because you can. Your time is more valuable than that.
  7. Be an Island: You cannot learn all of the things, and there’s no better way to find new opportunity than to meet new people. Engage the world around you, seek community online and offline.
  8. Work Yourself Out of a Job: Sure, you didn’t choose a creative profession just to find yourself doing sales. But if we only engage in our craft, one day we’ll finish a project and go white with horror as we realize we don’t know where the next check is coming from. We must learn to juggle promotion and production.
  9. Put All Your Eggs in One Basket: Failure is inevitable, but diversity builds resilience. Don’t set yourself up for catastrophic failure by having only one client, or one marketing channel, or one pitch.
  10. Lose Touch with Your Clients: The easiest way to grow your business is by selling more to the clients you already have. Stay “top of mind” with a newsletter and cards for birthdays or holidays.

I’m sure there’s a lot I’ve missed. What advice would you add?

Josh Simmons

Community Manager at O'Reilly Media

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