This story is going to “date” me a bit, but I’m sharing it as a parable. It’s about all the ways we convince ourselves that what we have is good enough – and all the ways that can hold us back.
Watch the story in the video or read the text below to learn more.

Back before the iPhone, there was a device called a Palm Pilot.  It didn’t have phone or internet capability. It was simply an electronic organizer – a place to maintain a calendar, a to-do list, and notes that didn’t require constant rewriting. I loved mine. My only frustration was having to carry that PLUS my flip phone. I kept thinking that there ought to be a way to merge the two.

Eventually, Palm did, bringing out a small device with a tiny screen and chicklet keyboard. I loved it. I could email and text, manage my calendar, and make phone calls. It worked for me.

Not too long after that Apple came out with the iPhone. It was beautiful and expensive. I convinced myself I didn’t really need it. I was happy with what I had. I watched my friends with their iPhones as one version after the other came out, and I kept thinking, “It’s okay. I’m good.”

At some point, about when the iPhone 3 or 4 came out, I realized I was falling behind. It occurred to me that I had another 20 years or 30 years left in the workforce. If I let myself settle for the technology that I had, I would fall very far behind.

I had seen that happen with my Dad who never really got onto computers. He worked for a small company that didn’t require it of him. But later, after retirement when he tried to find another gig, he couldn’t. Companies were no longer satisfied with sales guys keeping notes on paper. By then, sales teams were using laptops and software to track their calls. He had no idea how to use any of that technology, and so, there was nowhere for him to go.

The point of this story isn’t about keeping up with technology, though – although that’s a useful side note.

The point is about keeping up with your career. It’s an invitation to notice the number of years you have left in your career, and notice: What are you settling for now that might hold you back later?

I noticed that with 20-30 years left in my career, settling for old technology wasn’t serving me. For you it might be something else:

  • A boss who isn’t giving you new opportunities
  • A company where you’re not getting the next promotion
  • A role that doesn’t light you up, where you feel like you’re just going through the motions
  • Being a “good enough” manager, but not really someone who inspires great performance in your team

I think there are two main reasons we end up settling, rather than staying on the cutting edge.

The first is that there’s comfort in the familiar. It feels safe. I knew how to use my PalmPilot. I knew how to make that work for me. Moving over into an iPhone meant I’d have to figure out a bunch of new ways of doing things. It seemed easier to stay put with the technology I had. There I was with my little bitty two-inch square screen, and I could have had a whole iPhone screen instead. But I was settling because it was familiar and comfortable. To settle, I had to ignore what I was missing out on: all that extra functionality, the big screen, the apps.

I’ve seen far too many people do that in their careers, too. They convince themselves that it’s better to stick with what they know. They ignore the fact that their careers don’t really let them spread their wings. They don’t see that there’s so much more out there, that could be available to them if they were able to truly shine. They find it scary to think about truly stepping into their leadership or moving up or finding a new job somewhere else. They think, “What if I don’t have the skills? What if I can’t figure it out?” So, they don’t, and they lose years of progress in their careers.

The second reason people stay stuck – and this was true for me with the switch to the iPhone – is that upgrades require investment. For me, there was the purchase price of the iPhone, but also all the other pieces that went along with it: the charging cords, the extra headphones so I could have some in my bag, some at my desk, etc.

Moving up in a career also requires an investment. It takes time, energy, and commitment to build leadership skills and to find and land the next role that will propel your career forward.

My clients spend 3 – 6 months building their leadership skills and exploring new options. That might sound like a lot of time, but when you compare it to the remaining 20-30 years left in your career, six months is nothing.

Making the most of your time is where a coach can really help. When you have a proven strategy, you’ll focus on actions that will get you to your goals. Too many people hesitate to work with a coach but waste endless hours scanning through online job boards. That approach may feel like you’re doing something, but the reality is that it doesn’t work.

Of course, investing in a coach takes more than time and energy. Just like my iPhone, it’s also a financial commitment. Spending $5 – 10K on a coach can feel like a big leap. However, if you think of it as an investment in your future, it’s really a no-brainer. For example, if your next promotion earned you a raise of just $7,000, that would be an additional $140,000 over the next 20 years. And that doesn’t account for future promotions and pay raises. If you invested just $10k in working with a coach, you will have earned an 18% annual return on investment. To put that in perspective, the average annual stock market return over the past 20 years was just over 7%. Investing in yourself is a good move.

If you’ve been in the same role for more than, say, three to five years – or if you’re new to your role and have been stumbling along trying to figure it out on your own – it’s time to ask yourself if that’s really serving you in the long run. Is it getting you to where you want to be 10, 20, or 30 years from now? If not, let’s talk. Book a call with me at We’ll have a conversation and see what we can do to set you up for the career you deserve.

Recieve My Articles in Your Inbox

Every month, I dive deep to share insights and action steps that will shift your perspective and renew your faith in what’s possible. Receive these directly in your inbox by subscribing here.

You have Successfully Subscribed!