Permission to Fail… and to Succeed


By Sep 12,2017  0

As small business owners, we must have some self-confidence to strike out on our own. If not, we would still be working for someone else. But, that does not mean we do not lack confidence in some situations or that we do not suffer from imposter syndrome. How do we get past this? If you are still in-house and wanting to make that leap, how can you develop the confidence to jump?

In early years, I had the confidence I could learn what I needed to know but lacked confidence in both my technical and business skills. I knew I had a lot to learn, but also had the good fortune of a safety net. My boss at the time was willing to let me keep scaling down my hours as I developed my business, and I do not have children to support.

Over time, I gained confidence in my technical skills, yet shied away from opportunities to grow beyond a solo shop because I lacked the confidence in my business skills. I knew I would rather code than manage other coders. I knew I had systems that work for me, but these systems would need to be formalized for a team. I knew I am an introvert who prefers quiet logical work to endless meetings with others. Despite all of that, I gradually decided to quit turning away work and hire some help.


It is a complex answer. As a result of a regular meditation practice, I became more comfortable with being uncomfortable. My biggest obstacle is not wanting to get outside of my comfort zone. I have confidence in my development skills and my ability to learn new technology when necessary for a project. I found technical challenges, but nothing that caused discomfort. This was not the case in my business skills. So, I am building confidence in my business skills the same way I did my technical skills.  I research what I can, ask mentors for guidance and feedback, and give myself permission to try and to fail.

I have confidence I will fail. I have already done so, in big ways and small. Yes, it is frustrating and embarrassing, just like tripping over nothing and falling in front of an audience or deploying code that is less than perfect.

So what? Each time that we fail, learn from our mistakes and do better the next time, we gain confidence.  We know more now than we did before. We know what not to do. We may be confident we will not make the mistake again, or we may be confident we will have to make it again before the lesson sinks in. 

These small victories add up. More importantly we gain the confidence we can fail and bounce back. And the small failures matter less. 

Permission to fail does not mean sloppy work or lack of quality assurance, just that I accept there will be room for improvement in everything I do. A script that runs perfectly the first time is probably overlooking an edge case. If I can allow myself to use a debugger the first time I run a complex script, then I can allow myself to create an imperfect process that I will improve over time.

So, if you are an in-house developer thinking of making that jump, try these ideas:

  1. Show your work to someone outside of the organization and ask for an evaluation.
  2. Create a demo file to show off a cool technique you use and share it for feedback.
  3. If it is not currently a requirement for you, start estimating your time to complete features and compare your actual work time against it. This will go a long way when you are on your own, and will also help you now in stating when a new feature will be ready.
  4. Talk to independent developers who have made the jump and learn from their mistakes. You might even find one who could use some subcontracting help. Picking up a few small subcontracting gigs on the side can help you get a feel for working for clients. It might even turn into something more.

I have since read that pushing yourself outside of both physical and mental comfort can result in “a more youthful brain that helps maintain a sharper memory and a greater ability to pay attention.”

So, worst case, if I fail at being the boss, I can go back to being a solo shop. And perhaps I have kept my brain young. But the upside… why not try?


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Mindfire Solutions
Jeffrey Scornavacca

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