How to Navigate a Career Change

🚀 What if you’re no longer on the right path? – Issue #149

Maybe it has something to do with moving up into the Sierra Nevada mountains after spending over 20 years of my Tech career in Silicon Valley. But, I keep thinking about the similarities between successfully navigating a lifetime career and climbing a mountain.

I know that sounds a little strange. But, bear with me.

As you are just getting started, from a distance, the mountain looks deceptively smooth, and the ascent seems like it must be accessible. But, you’re never prepared well enough, and each step of the way has some surprise.

As you get closer, you select a point that you consider to be your summit. You choose a reasonable path, and you begin climbing.

However, once you are in the thick of things, you can no longer see the summit or even the entirety of your chosen path. All you can see is what is right around you.

What seemed accessible from a distance is now rocky, challenging, and occasionally treacherous. You may discover that your path is blocked.

You find that you have to change course to continue your upward progress. You even have to backtrack occasionally to find a way around and start up a new trail.

Finally, as you ascend and get closer and closer to your original summit, new vantage points may reveal that it isn’t what you thought it would be. That “summit” isn’t where you wanted to end up, and now you can see other goals that are more appealing. 

You’re stuck and can’t decide how to proceed.

Prepare well

Just as you would prepare for an actual mountain climbing expedition, you need to plan how you want your career to turn out. You can’t just toss a few things into a backpack and wing it. 

Do that, and you’ll most likely end up somewhere you wish that you were not.

Spend some time understanding who you really are and where you want to end up in life. Think out 10, 20, or even 30+ years. 

Deeply understand your talent, strengths, capabilities, knowledge, and experience. Where can they take you? Where do they lead you?

Envision a summit that would make you feel satisfied and fulfilled.

Plan multiple paths

It’s a lot easier to map out alternative routes when you have some distance and perspective. Once you’re neck-deep in the daily grind, you will lose sight of what options might be possible.

We all do.

I call this having your Plans A-D:

• Plan A will be your initial ascent. Given your best planning and thought, this is the path that you think will take you to the summit that you want. I remember when this was my career plan at eBay. I wanted to be a Head of Design.

• Plan B is a course correction that looks like a reasonable alternative path to your desired summit if Plan A goes wrong at some point. For me, this is when I left eBay to join Yahoo and became the VP of Consumer Products for Search. A GM role seemed to be my new summit.

• Plan C is an entirely different course of action that leads to a separate summit that you think would also be desirable. I activated my Plan C when I decided to leave the corporate world and become an entrepreneur with my own consulting business and founding a startup (i.e., my new summit was founder and CEO of a company). Eventually, this Plan C becomes your new Plan A, which has been the case with my work as a leadership coach and career advisor in my own business.

• Plan D is what you fall back to when a surprise storm hits. When everything fails, and you need to go into survival mode for a while, Plan D will keep you going. For example, I have my eye on a job at my favorite local hardware store. I love tools. 😉

A limited window of opportunity

There are some paths and peaks that you don’t want to attempt at night. I remember my brother telling me about one of his climbs in the Rockies that started later than planned.

The path was excellent in the full daylight, but darkness began to fall. It became increasingly treacherous, and he wasn’t sure that he was going to make it back down safely.

Unfortunately, some careers are the same.

You have a window of opportunity for your ascent — obviously measured in years, not hours. But, you still have to climb fast and hard, to have any chance of reaching the summit.

If you slow down, take breaks, and make camp along the way, you’re in trouble. You may not achieve that peak.

My friends in Silicon Valley Tech know this. Over drinks, people will become more honest and say, “If you’re not a C-level executive by 50, you never will be.” 

Ageism is alive and well there.

I know that several professions have similar issues with ageism. If that is true of your industry, then make your plans and climb fast.

Otherwise, identify a career summit that doesn’t discriminate for any of the reasons with which we’ve all become sadly familiar (e.g., ageism, sexism, racism).

We all get stuck

It’s normal to feel stuck or stalled at some point in your career. There will be times of rapid advancement (i.e., frequent raises and promotions), and times that it seems to slow to a crawl.

If it goes on for too long, you may need some strategic job-hopping.

It helps to have a supportive “scene” and a peer group that will listen, give honest advice, encourage, and support you in your climb. I also think it is critical to have a realistic “career hero” in mind, which I wrote about recently.

This person might be someone who has made the ascent before you and knows the twists, turns, and surprises on the path. He or she has reached the summit and understands what you will face. If you’re lucky, this person could even become a mentor.

It’s OK to ask for help

The smart climbers never climb alone. They know how risky that can be.

If something goes wrong, no one else is there. It is best to have partners who encourage, guide, and help each other.

Many of us let our pride get in the way of asking for help when it’s appropriate. We don’t want to look weak or foolish. We don’t want to admit that we’ve made a mistake.

It’s unfortunate because letting yourself be vulnerable and asking the right person for help can create the exact breakthrough that you need.

Best of luck!

I wish you the best of luck with your career ascent. Plan and prepare, surround yourself with the right people, stay focused, and climb hard. Don’t be afraid to make a change if it is necessary.

Life is too short to be miserable. It is too precious to waste chasing a career goal that isn’t what you thought it would be.

You do have the right to choose a summit that will fulfill you.

Don’t forget that making a change doesn’t have to mean starting over. If you need any help transforming your career and putting a plan together, reach out to me. It’s what I love doing. 😀

Quick Tip – You don’t have to start over

Ascending the summit of your career has a distinct advantage over climbing a physical mountain. There are some ways that you could switch to a different summit mid-climb, but they are pretty intense.

When you decide that a particular career summit is no longer right for you, it is very discouraging. Part of you wants to push on and keep going, even if you’re miserable.

After all, you’ve put so many years — or decades — into this specific career. That’s the good ol’ sunk cost fallacy at work.

If you now have your eye on a different summit, you can’t even imagine climbing back down and starting over at the base of a new mountain. I was in my 40s when I did this, and I can confirm that the thought made me sick to my stomach.

I had spent almost 20 years climbing in my old Tech career; getting a Ph.D., scrambling from being an intern at IBM to landing a dream job at Apple, then a series of startups and entrepreneurial adventures, moving up into management at eBay, and finally becoming a VP at Yahoo.

Start over from the bottom of a new career? 😞

So, I rejected that reality, carefully constructed my new career path, and hit the ground running. Think of it as paragliding from one mountain top to another.

Terrifying? Yes, it was.

It was loaded with immense challenges, hard work, and long hours. But it was worth it.

I love what I do now, and it’s rewarding to help others with their career challenges.

I know that you can do this too, if you decide that you want to pursue a new career summit. 

You don’t have to start over. 

You can leverage everything you have learned and the skills you have acquired to kickstart the new career!

Are you considering a significant career change? What are you doing to prepare?

Companies Offering Remote Jobs

• MailerLite was born in 2010 to give businesses a simple yet powerful email solution to help them grow. They have several remote positions available for writers, engineers, and more.

• Creative Commons is a nonprofit organization dedicated to building a globally-accessible public commons of knowledge and culture. They make it easier for people to share their creative and academic work, as well as to access and build upon the work of others. They have two high-power positions open right now: Chief Executive Officer and a Director of Finance.

• Chef Software is the industry leader in IT automation and DevOps solutions. They develop the world’s best products for managing applications and infrastructure at scale, and they deploy them against real problems in all kinds of industries. They have a few remote positions available.

🎁 Do you know someone who is considering a career change? They might find this edition to be helpful as they make a new plan.