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Michael Gardon

  • Writer's pictureMichael Gardon

Your Career Is Riskier Than You Think. Here's How To Manage It. - The Break 33

Updated: Mar 19



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Today's Issue


This week you'll learn how to manage career risk:

  • Everything - including your career - has an element of risk

  • 80% of dealing with uncertainty is preparation

  • 9 ideas to help you manage risk in any career


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Your Career Is Riskier Than You Think


Last week I wrote about the Hero’s Journey I think we are all on. How it is in The Unknown that anything worth doing resides.


The Unknown is risky.


But what most people miss is that The Known is also risky. How can that be?


Because most of what we think is certain, actually isn’t.


Most advice we listen to is given as certainty. That’s why I have a healthy distaste for “experts.” Reality is messier. Reality is probabilistic - you can make a “good” decision and be wrong, you can make a “bad” decision and be right.


“Experts” say things like these with certainty:

  • Buy a house because they never lose value (I’ve lived through two periods where this isn’t true)

  • Go to college, it’s an investment that guarantees you a good job (eh, it’s more like a $100k anchor around your neck and you’re no closer to figuring out what you should do with your career.)

  • Work hard and save for retirement (until you realize that you haven’t really lived for 60 years of your life.)

  • Get a good job. Pay your dues, and good things will happen. (Until you get fired from your safe job because your tech company thought profits didn’t matter because infinite growth was inevitable.)

Everything in life has an element of risk. Including your safe job.


So, even if you’re not remotely worried about losing your job, you should prepare anyway, as my friend Dave Kline says:



Here’s how.


9 Ways to Manage Career Risk


1. Build a large, high quality network.


Every single career BREAK I have made is due to my network. In fact, I’ve only had to produce a resume as a formality after I already got a job.


I’ve also seen make introductions that have changed people’s lives, and that is incredibly gratifying.


Connections and relationships are where its at.


But even I made mistakes here. I’m an introvert at heart. I used to want a small, close network. As I’ve seen the power of a good network, I’ve worked to come out of my shell and be more outgoing, taking more risks and being bolder with building connections.


Go big, but don’t for get the golden rule of networking - give first.


2. Make LinkedIn your priority.


How can you build a large network quickly?


Throw your resume away and make LinkedIn the hub of your life’s work. LinkedIn is where you can build your network in a meaningful way. Build, talk, network and debate in public - you never know who’s watching.


Since I’ve made LikedIn a priority, I have:

  • Been on podcasts

  • Found guests for ** The BREAK **

  • Signed a sponsor

  • Spoken at a conference

  • Got my first coaching clients

  • Become friends with big influencers

  • Got my ass in shape

If you need help with your profile, start with the best linkedIn writing services (or DM me for additional recommendations of who to follow on LinkedIn for this topic).


3. Go generalist.


Most career advice peddlers will tell you to become exceptional at one thing. That certainly can bring you success, but it also leaves you vulnerable to a dynamic and rapidly changing landscape.


How do you think the photo film designers at Kodak felt when digital cameras came out?


It pays to diversify your skills set and develop abilities in multiple areas.


I’ve always had a hard time articulating what I am good at, but I know with certainty I can get 80% of the way in almost anything and that has allowed me to survive and adapt in tech.


4. Be likable.


What’s one way to instantly connect with new people? Be likable.


Low hanging fruit, but . . . positivity and liability increases your luck surface area . As Sahil Bloom puts it: “pessimists sound smart. Optimists get rich.”


Embrace more positivity.


Have some energy.


Give yourself and others some grace.


Be helpful and upbeat.


Give more than you take.


Life is positive sum, it’s not tit for tat.


5. Be reliable.


Again, low hanging fruit. The bar is very low to stand out. Unfortunately, reliability is in short supply.


Just do what you say you will do.


Be on time.


Show up.


Keep your word.


This goes for at your job and while building your network.


6. Hone the holy trinity of meta skills.


What’s the holy trinity?

  1. Written communication. The ability to write concisely, persuasively and for impact is a huge skill especially in remote first/digital environments. I hire for written communication and know tons of other CEOs that do as well.

  2. Verbal communication. The ability to speak concisely, persuasively and for impact is a huge skill today. No one wants to talk anymore, but people who can communicate verbally show their presence when big decisions need to be made. P.S. good comms make you more likable!

  3. Getting Shit Done. GSD is an art form. You can have 0 hard skills and still develop a reputation for getting shit done. I’ve seen it (and experienced it) time and time again. Who do you want on your team? The smartest person, or the person you know can execute?

You can do anything with these three skills and you can take them wherever your career takes you.


7. Always have a consulting business on the side.


You have a job. You get paid for some skill. You could provide those same services to other companies/people/entities.


I have had a “consulting” business since 2012. I have used it in between career moves twice, and taken on countless side projects over the years.


When my first startup failed, I became an early stage business consultant. I replaced my income in less than a month.


When I left another startup, I used my consulting company to get long term contracts with a Fortune 500 company, and ended up working with them for almost 3 years.


Use your side business as part of your networking story and see what happens.


8. Build a side income stream.


Side incomes are the new savings account.


Similar to #7, I have found that having a side income not only diversifies your income in case of a job loss, but perhaps more importantly, serves as a creative catalyst if your day to day job is drudgery.


Some ideas:

  • rental properties

  • website/blog

  • physical product like Quotebook

  • course

  • coaching kids sports

  • teaching

9. Save money and keep a cash cushion.


Ok, I saved the boring stuff for last.


The most critical aspect of a new business is runway - just being able to stay in business long enough to figure it out. Same is true with the startup of you. Just live below your means.


Aim to have at least 6 months of cash in the bank.


Understand what expenses you can cut immediately if something bad happens.


Cash in the bank is the ultimate option for you to walk away, invest in yourself, start a business or buy a business.


I’ve met tons of people who have changed their lives just because they had some cash laying around and decided to bet on themselves.


See you again next week!

3 ways I can help you:


1. Book a free Intro To Advantage Mapping coaching call . In this 30 minute, no obligation call, we'll get you executing on a high odds career path by leveraging your natural advantages and Circle of Competence.

2. Find your new job! Remote tech jobs curated for you. Follow me on Pallet .

3. Get in the Breaking Work conversation on Linkedin. Messages are open. Follow me here .


The Break Job Board


I teamed up with Pallet to create a curated job board for our community ! These jobs are tech focused, remote first opportunities. I’d love it if you followed. Maybe, just maybe you’ll find your next big opportunity here.


Here are a few featured opportunities:

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What’s happening on the pod?


Manoj Jonna is the Co-Founder & CEO of Ramped , a skills-based hiring platform that is revolutionizing the job search. Prior to Ramped, Manoj served as Chief Strategy Officer of Reservations.com and as Vice President and Founding Team member at YayPay. Before YayPay, he worked as an investment banker at Deloitte Corporate Finance where he focused on mergers & acquisitions. Manoj holds a JD from Georgetown Law School.


You made it to the end! Hopefully you learned something about breaking your career today! If so, please share this with someone you care about.


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⭐️⭐️⭐️⭐️⭐️ This was super helpful! ⭐️⭐️⭐️ Could be better. ⭐️ This one needs work!

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