How Do You Know When to Take Career Risks?

(Photo credit @claybanks)

Venture capitalists are by definition investors who take calculated risks, and usually really, really big ones. Their goal is to invest in multiple companies with the assumption that the majority of them will fail, but at least 1 out of 10 will yield 10X or higher results (which will hopefully make up for the failed investments). They spread the risk out. They listen to hundreds, even thousands of startup company pitches and select the ones they think have the best chance of success, after evaluating the company’s management team, the financials, the tech’s potential, etc.

And even with all the resources at their disposal, they get it wrong ALL the time.

So please don’t think you have to have everything figured out completely before you decide to take a career leap. And know that you’re going to make some mistakes along the way - but that’s ok!!

Let me offer you some tips and strategies to help you with this type of career decision-making.

With VCs being taken in by the hype, how can you avoid joining a leaky ship (aka a bad startup)?

• Try thinking of making career changes as taking calculated risks. For some, it’s helpful to think of a chess game. How many moves ahead can you plan out and how does that help you decide what to do today? When/how do you need to shift strategy when your “opponent” throws up a surprise move (aka a life change, an industry shift, or an economic downturn)?

• Learn to identify your risk tolerance. I talk often with students/clients about identifying your ‘risk tolerance.’ Everyone has a different way of assessing risk in their career and in figuring out how much risk they can handle at any one time. Remember, it can also fluctuate based on your age, family dynamics, finances, etc.

  • Check out this article for more details on the RRIS method for improving your risk tolerance.

• Face your fears. You can also work to increase your risk tolerance by trying this fear-setting technique from this famous guy Tim Ferriss I knew in college.

  • The aim of the exercise is to name your fears so you don’t let them lurk in the shadows and prevent you from taking big actions. I was surprised by how helpful it was the first time I did it, that even though I scared the hell out of myself, it felt great to vocalize my fears and face them!

  • Here’s another take on this fear-setting exercise too.

Another way to make hard career decisions is by educating yourself so you aren’t leaping blindly.

• What universal skills do you have? You can educate yourself about your skills by taking assessments like StrengthsFinder.

• Learn about the startup landscape. You can also use some of the tools the VCs do to educate yourself about the startup landscape & specific niches within it (fintech, 3D printing, IoT, etc): CBInsights and VentureScanner.

• Get recommendations on top startups to join. Wealthfront also does a yearly career-launching companies blog post, and provides great criteria/methodology for how to choose among one of these organizations.

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Want personalized career guidance? Take a look at my Career Strategy Session options.

Having a futurist mindset

(Photo credit @fabiolucas_foto)

While not everyone needs to be a futurist to work in tech, it helps to borrow from their mindset. Here are a couple tips to help you get started. 

1. Practice making decisions without much information.

• Make it small at first. 

  • Try picking a local restaurant or an activity without reading any online reviews. 

  • What are other cues or factors that help you decide if it’s going to be a good experience or not? 

    • Location? Name of restaurant? Write these factors down so you can review them later to see what information was useful or not useful.

  • Afterwards: evaluate how did it go? Did it meet your expectations, or exceed/underwhelm you? 

    • Ask yourself the critical question: Why?? What info would have helped you make a better decision? What proxy info could you have used to  

• Then, escalate the decision to something with more impact. Try thinking about a larger decision you need to make that you are or have been uncertain about. Is it related to choosing a new job or career? Deciding what city to live in?

  • Use the questions & criteria you saw above & modify them to fit this scenario.

    • Curious about whether you should become a programmer? Try Hour of Code & see what you think.

    • Thinking about a new city? Can you do a virtual visit there via a Chamber of Commerce site or similar? Can you find a friend to help you learn about where they live?

2. Imagine that this is an interview question - for life - and try to see how many experiences you’ve had where you didn’t have much information, yet made the decision anyway. 

• Prompt: “Tell me about a time when you had to make a decision without all of the necessary information. What happened? Why did you have to make this decision in this way? What did you learn from this experience, and how did it impact your future decisions?”

  • If you don’t have many experiences like that, go out and get some. 

  • Think of it like a muscle that you need to exercise regularly, not a skill that you can be ‘certified’ in. You have to practice it often, especially when the stakes get higher and higher as your career progresses. 

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Want personalized job search strategy tips and career guidance? Take a look at my Career Strategy Session options.

Does a futurist really use a crystal ball to forecast trends?

(Photo by @8thshot)

I will admit that during these times of endlessly being at home, I *may* have started re-watching old episodes of Charmed on Netflix. (Stop judging.) Putting aside the campy antics, you have to admire the consistent battle against what the future will bring and how to best prepare for it. (Tho in our case, we’re not battling demons that can be vanquished with a potion...or are we?). 

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#techtopic

One of the interview questions I love to ask in mock interviews is “Tell me about a time that you had to make a decision without all the necessary information.” Most students hate it. It throws them off-guard.I have had more than one tell me that they don’t make any decisions without all the information in front of them -- which is ludicrous. We make those types of decisions daily - small/easy (like trying a new brand of clothing out) or large/expensive (selecting a painter for your large Victorian home). 

Employers in tech want to know that you can make decisions with imperfect or missing information, because often, that’s what daily life is like, regardless of sector. 

While it’s tempting to assume that leaders have crystal balls or access to oodles of secret information to help them make decisions, it’s actually more of a method than a map. 

Again, this is where I think tech, the scientific method, agile development, etc provide an advantage to those trying to do strategic planning in heavily uncertain times. You could also try learning from those who are called ‘futurists’ to see the frameworks that they use to help guide others in decision making.

So what is a futurist, you ask? 

According to Amy Webb, “A futurist is someone who studies next-order outcomes using signals from the present.”

Want to make more decisions like a futurist? Check out these articles & resources:

• Articles

  • 5 Principles for Thinking Like a Futurist

  • How to do Strategic Planning like a Futurist

  • Getting the Restart Right: How to Lead When Nobody Has a Map

• Resources

  • Frameworks for making future decisions

  • Futurist Resources

Here are some of the Futurists that I follow to keep up on trends & signals & predictions: 

• Juan Enriquez

• Mary Lou Jepsen

• Alison Sander

• Amy Webb

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#space

Sad that the launch was postponed? Check out this article to learn Why SpaceX has to wait until next Saturday to launch 

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