Stuck? 6 Ways to Approach Your Career Like a Caveman

The digital economy is changing everything, average is over, and the only solution is for you to take the reigns, become the CEO, pivot, plan and INNOVATE, baby! There’s only one problem, and it’s a big one: We are not machines. We are flawed, fear-prone, desire-driven, often-irrational HUMAN BEINGS.

As soon as we ushered out the era of the career ladder, experts and pundits (myself included) started trumpeting the parade of thinking of yourself like a start-up! A brand! A smart phone!

It makes sense: the digital economy is changing everything, average is over, and the only solution is for you to take the reigns, become the CEO, pivot, plan and INNOVATE, baby!

There’s only one problem with this line of thinking, and it’s a big one.

We are not machines. We are flawed, fear-prone, desire-driven, often-irrational HUMAN BEINGS.

As my friend Peter described it during one of our email conversations on this topic:

“People are NOT companies. A company is a dispassionate entity that is only as irrational as the people pulling the strings. But in the start up of you, your obstacles are primarily emotional. We’re psychologically unprepared for the exponentially accelerated change that technology is driving — in our workflow, our economy, in our big corporate company culture. We are apes who crawled out of the ocean not that long ago (in the grand scheme of things) — and we’re still operating on that hardware.”


I do believe in re-framing career as a non-linear progression, hence the smart-phone analogy that I use: you get to download all the apps you want and need to feel fulfilled, so long as you remember to recharge, clear clutter and build a support network.

But what do you do when you’re entire operating system needs an upgrade?

It’s not as easy as clicking “update now” and waiting five minutes for a shinier new sheath to set in. If only reshaping our career (and lives) were as straightforward as that.

What we forget, or fail to see, are the MONTHS (sometimes years) that entire teams of people at Apple, let’s say, spent toiling over every pixel to get that one-click download ready for showtime.

So what’s the solution? Time to take a page from the days before technology was even in the picture.


I’ve talked about our fight-or-flight response as it relates to speaking like a pro, but did you know it may factor in to your ability to navigate a big decision you’re staring down?

In my work with dozens of coaching clients and friends on the cusp of a major career, life or relationship change, I’ve noticed that many come to me at the point of Fear + Freeze (or Fight). They know they’ve hit a ceiling, they know in their gut it is time to change, but they are afraid. And so they freeze or fight the reality of how they really feel. I’ve been there.

Career changes in particular trigger and often appear to threaten the most fundamental needs that we have for food, shelter and clothing. Our fear response tells us that if we make one wrong move, we’ll soon become homeless and unemployed, unable to fend for our very survival.

Perceiving this potential threat to our primary needs, our creative faculties shut-down (or get clouded over by fear-based thinking) and we freeze, flee, or fight that pestering voice that seeks greater purpose and meaning. Get off your top-of-the-pyramid self-actualization high horse! We want to shout to the scary person within us instigating this next phase of our evolution.

In order to make any progress at all, you need to think of your career like a caveman.

Here’s how:

  1. Create a safe environment. Let’s use the example of a coaching client who might want to leave their job. I take them through their current state: what’s working, what isn’t, what they would want in an future scenario, how their ideal average day plays out. We might even go through pros and cons of their current job, then pros and cons of a different one. 45 minutes in I’ll ask, what does your gut say? They almost always know, and can state it with confidence. The pros and cons may have helped, but the hidden helper here is the relaxed environment, the open dialog, and the feeling that they are not alone. One of the most powerful things that a friend said to me last year was, “I will hold you up even when you can’t hold yourself. Keep going.”
  2. Get your body right. You won’t have a snowball’s chance in hell at your best problem-solving abilities if you aren’t eating well, sleeping enough, getting outside or exercising (even just walking or light movement). Focus on the fundamentals before putting too much pressure on yourself to be brilliant.
  3. Get clear enough to ask for help. If you can suspend your fear for a moment, what is it that you really want? (the classic “if time or money weren’t an issue” comes to mind) AND: what, specifically, would be most helpful in this moment? See if you can pinpoint exactly what you are stuck on. Are you lacking clarity on your talents and strengths? Or needing to build-up a specific skill such as sales and marketing? Would it be helpful to hear how someone else navigated a similar situation? Identify what is creating the bottleneck in your brain; if you can do this, you can start to ask for more targeted help.
  4. Call upon your community. Start talking to people. Set-up 30-minute calls like it’s your job. We survived on the savannah because of teamwork and cooperation. Friends, family and trusted advisors can be a major boost to feel safe enough to take risks. Figure out who, specifically, can help in the areas you’ve identified above.
  5. Celebrate the small wins. Given that hunter cavemen would often go for days without a big kill, they relied on their their gatherer counterparts to bring home the berries. It’s critical that when you are undergoing major change you learn to take just one small brave step each day, and recognize yourself for doing little things that can add up over time. These additive wins will sustain you over the long haul, and even out the rollercoaster highs and lows of the big risks, successes and flops.
  6. REST. And take as much alone time as you need. For all the benefits of community, major life changes can also be intense, exhausting and overwhelming. You may not feel fully like yourself. As Martha Beck would say, “Play (her view of work) until you feel like resting, then rest until you feel like playing — and not a minute sooner.”


Though admirable and certainly well-intentioned, there is often nothing more frustrating to a Stuck Person than an immediate bombardment of your best advice.

It’s a bit like helping someone search for lost keys and asking, “Where did you last leave them?” If they knew, they would have them! Similarly, if your Stuck Person knew what would send them sailing past their impasse, they would absolutely be doing it. Nobody wants to be hitting their head against the Great Wall-O-Stuck every day.

Rest assured that your Stuck Person is smart and resourceful, has likely been wracking their brain 24/7, is exploring all options, reading The Internet like it’s their job, and talking to anyone and everyone they can.

Coming from a person who felt frustratingly stuck across several areas of my life of last year, I found the following tips to work well for clients and myself:

  1. Start simple with a heaping dose of empathy — it goes a very long way.
  2. Check-in before you dish out. It’s not that your advice won’t be helpful — it absolutely can be (outside perspective is critical in cloudy times like these), but either wait for the ask or say, “Would it be helpful to brainstorm a little bit? Even if not right now, I’m available any time.”
  3. Ask big questions. The best questions are big, broad and open-ended: “What is your ideal outcome?”, “What does sound interesting to you?” or the trusty aforementioned “What does your gut say?”
  4. Ask short-term survival-mode questions. Take them right to the present moment with questions like, “What would be most helpful today? Is there anything you need right now from me, or to do for yourself?”
  5. Best yet, boost their battered confidence with what you perceive as their biggest strengths, examples of times you’ve seen them triumph in the past, and perspective on how this very challenge may fit into their “life movie” — the start to an epic journey with important lessons to learn. If you mean it, reassure them that they WILL come out of the fog feeling stronger and wiser, and that you’re available to chat when things get tough.


Not an option for the caveman of yore, we have the perk of resources available instantly at our fingertips. The Unstuck App for iPad is awesome. For a sample of their content, check out their cool year-end tip cards.

This article originally appeared at Jenny is an author, international speaker and career coach who helps people and companies optimize systems at the intersection of mind, body and business. To kick off the new year and help you make plans, plot your next big leap, or just plain get unstuck, sign-up for a 60-minute Strategy Session. Follow her on Twitter @jenny_blake.