What to do when you don’t know what you’re doing

Just ten days after leaving the big company I’ve worked in for twenty years, I’m facing things that I have little or no experience dealing with. How do I describe and package what I do? What do I offer for free and what do I charge for (and how much)? There are legal, financial, and technical issues to sort out. It can be overwhelming, and makes the well-defined boxes inside big companies a bit more appealing.

Here are five things that have helped me already and might help you if you’re trying something new. They’ve made me feel less anxious and more confident, and so the entire process is more enjoyable.

What am I doing?

Find people who already do it.

You can learn a lot from simple research. When I started charging for presentations at a conference, for example, I looked online to see what others like me have charged. For my new online course, I searched for examples of similar offerings.

I’ll reach out to people who have more experience and ask “What do you think?” That research gives me at least a sense of what’s appropriate.

Talk with trusted confidants.

It takes a friend to give you constructive criticism or spend the time to think through an approach with you. It also takes vulnerability - I don't know what to do. Will you talk with me about it?

In the past I kept my biggest issues to myself and that was a mistake. Now I’m lucky to have a handful of people I regularly go to for coaching and advice. They're trusted advisors who care enough about me to to tell me what they think is best, not just what I want to hear. If you don’t already have such a circle of advisors, start cultivating them now. You can begin by approaching someone you respect and asking “Would you help me?”

Fail small, fast, and cheap.

After reading how modern start-ups begin and grow, I’ve tried to adapt those ideas to myself. A big part of that is breaking down something you want to do into small, cheap experiments. That allows you try different things and quickly get feedback that helps you learn and create the next experiment. You start small and iterate.

My weekly blog posts led to a book. Free courses I created led to on-line and custom programs I can charge for. The hundreds of free talks I gave led to speaking engagements and a TEDx talk.

I didn’t create risky plans for the start-up of me. I just tried a series of low-risk, low-cost experiments that allowed me to discover things I enjoy doing that also have a value to others.

Frame it all as a learning goal.

I must have told myself “I’m terrible at this” (and worse) more than ten thousand times. And each time I try to remind myself “I’m just not good at it yet.” That is the essence of a growth mindset, and that simple switch in your head changes the entire process.

When trying something new, of course you don’t know how to do many things. What else would you expect? By framing what you’re doing as a learning goal - not to be good or bad but to become better - your ignorance and mistakes become opportunities for improvement instead of sources of suffering.

Keep shipping.

The biggest lesson I’ve learned in the last decade has been this: persistence and passion trumps all else. When you keep shipping - trying new things, delivering, deepening relationships based on contribution - all your fears, detractors, and mistakes no longer define you. They’re behind you because you’ve kept going, and the passion you show over time attracts others who care as you do.

Have you tried something new and thought “I don’t know what I’m doing”? Don’t give up. It can be a beginning instead of an ending.