How We De-Risk Big, Scary Moves – The Worth Project

by admin

Earlier this week on our podcast, we had Belma McCaffrey of Work Bigger join us. She shared her insight and her own personal story about finding a career that filled her with purpose.

This clearly struck a chord with some people and I started receiving numerous questions like “Ok great. I know what I want to do now. But what about my FEAR? How do I even begin to move past that?”

Oh, I get you. Knowing is one thing. Doing is, quite clearly, another.

Both Jordan and I are currently working through this. Jordan is in the midst of a career transition. He’s been with his company for 14 years — it’s the only company he’s worked for — and he’s trying to figure out what’s next. Does he continue to take a new role with them? Does he take a break? It’s a big question (and yes, his employer knows he’s struggling with these issues. I’m not outing him on this blog.). This career uncertainty is scary for him.

To balance his career transition and to keep pursuing my own goals, I am stepping up my work. I’m actively building up my consulting business and balancing that inconsistent income with some freelance writing. But, as I’m sure many self-employed people can relate, some months I feel like I’m covered with work and other months I wonder where everyone went. This income instability is scary for me.

Our big, scary risk right now is trying to navigate these two changes simultaneously.

But it’s not the first time we’ve dealt with a career transition. I made a big, scary move a few years ago. And I didn’t make it well.

My Scary, Risky Move

Have you ever missed your exit on the freeway? This sounds weird but whenever I miss my exit or my turn and I’m driving in the wrong direction I find it excruciating. I count the minutes that I’m wasting going the wrong way and if the next exit is miles down the road, it feels like torture.

That’s how I felt a few years ago when I was in the wrong job. I knew on the first day it was the wrong job and I was going down the wrong path. But what are you going to do? Quit on the first day?

I should’ve. I lasted seven months before the whole thing was too much. (I wrote more details about it in this newsletter).

Eventually, it was so bad I couldn’t stand it for one more minute. I left everything and walked out.

I walked out to nothing.

This was a scary, risky move. There were a lot of tears. A lot of stress. And a lot that I would re-do if I could.

So this time we’re doing it differently.

De-risking a big, scary move

A couple of weeks ago I received a newsletter from Carl Richards, author of The Behavior Gap. In it, he shared his 5 steps for de-risking a scary thing:

1 – Guess

2 – Test

3 – Act

4 – Learn

5 – Repeat

(PS: his articles are all great and include sketches that are much better than what I just wrote.)

He went on to share that we often hold ourselves back from doing scary things because we want a certain outcome. We’re not down with uncertainty. We don’t like it when we don’t know that things are going to work.

In the article about ditching someday, I shared that this is human nature. We like certainty, even if that certainty isn’t ideal. We’ll stay in bad situations because we prefer that to the unknown. We want to do something different but we’re stuck in analysis paralysis mode because it just feels a little too scary.

What I love about this simple, five-step process is that it moves you slowly outside of your uncertainty. It gives you permission to test and learn. Repeat this process enough and you’ve done the scary thing without being consumed by fear.

When I read that email, I realized that this is exactly what Jordan and I have been doing the past few months to de-risk his scary career move by making sure that the consulting business is earning enough to sustain our family during his career changes.

1. Guess

We’ve guessed that this business will be something we can scale to bring in enough income to fully support our family. I think if I focus on larger clients, bigger jobs, and stay in an industry niche I’ll be able to build this to what we need. But is that true? I don’t know. Right now it’s just a guess. It’s scary, but it’s ok. (PS: we used this spreadsheet to calculate how much the business would need to bring in to support us.)

2. Test

We’ve designed the test. We figured that if I wanted these bigger clients, we need to provide something that they think is really valuable to showcase what we can offer. Rather than going the traditional route of traveling to conferences, doing PR, or writing a million articles we decided that the right move was to do a study and publish an in-depth white paper.

3. Act

We’re in the midst of this right now. Currently, we’re doing the research, outlining the white paper, and reaching out to experts to let them know that we have this study coming out. This doesn’t feel risky. It feels like I’m in the midst of an experiment.

4. Learn

Here’s what we hope to learn: will this new approach to attracting clients get us to a sustainable place with business revenue? Sustainable enough that it can fully support our family expenses while Jordan can have the breathing room he needs to figure out his career steps?

5. Repeat

If the test doesn’t result in a big YES, we’ll adjust and try again. If it does come up with a YES, how can we create a new test to keep building off that insight?

I like that when we get to this point it doesn’t feel like a success or a failure: we try things, see if they work, and then adjust accordingly.

This isn’t only a process that you can use while building a business. I actually used a similar process without realizing it when I wanted to transition from being a CPA to working in marketing. I didn’t jump in with two feet and hope for the best, like I did when I walked out of that job a few years ago.

I de-risked the career change by testing my interest in the new career and calculating the financial change.

  • I first set up coffee dates with anyone who would speak with me and learned about their career path in marketing.
  • With that data I narrowed down my focus.
  • I then took an online course (before that was really even a thing).
  • I attended workshops.
  • I researched average salaries and made a rough budget to see if I could afford to change paths.
  • I went to get my MBA (unnecessary to the process, but a personal goal).
  • I took an internship.

And then when I finally made the career jump it wasn’t scary. It was easy.

Let’s hope that with the learn and repeat cycle this new change Jordan and I are undertaking stays not-so-scary.

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