Turn Jobs Into Journeys

Photo by Vlad Bagacian on Unsplash

I remember when I graduated from college in 1997, the goal was to simply “get a job”. The implication was that once I had a job, I could shift my focus to keeping the job. And that would be that. I’d hang onto that job as long as I could and then, someday, retire.

This is not the experience of people coming out of college today. In fact, not everyone entering the professional workforce is coming out of college because college is no longer the gatekeeper for professional careers. The notion that you learn learn learn and then graduate and get a job has finally been shattered. More and more, we are recognizing that, if approached with a growth mindset (see Carol Dweck’s groundbreaking work on Growth Mindset), work is a fantastic arena for learning and growth. We no longer learn so we can work. We now learn while we work.

We no longer learn so we can work. We now learn while we work.

Photo by Vladislav Babienko on Unsplash

How did that shift come about?

Let’s create some context here.

As of 2014, 34% of American workers were freelancing. (Kleiner Perkins Internet Trends Report) And that number is expected to rise to 51% by 2027. (Freelancing in America by Upwork and the Freelancers Union) That means that half the workforce is not even trying to keep their jobs. At least not in the traditional sense. More accurately, they are not trying to keep their jobs with their one and only employer. They are actively looking to go from job to job.

Employees see this as a way to diversify their experiences which keeps their work interesting. They also see it as a way to control their own schedules and carve out the freedom that they desire.

There are advantages for employers in this new model, too. Employers can avoid paying health insurance and committing to annual salaries. They can lower their overhead. But employers who are trying to build consistency so that they can provide consistency for their customers are struggling to retain their people.

When employees jump from job to job, they have new environments and new opportunities for learning and growing with each new job. They meet new people, face new challenges, stress-test their strengths and uncover and work on their weaknesses.

If employers can’t say that about the opportunities they provide for employees, they are competing against the independence that modern employees crave. According to the Kleiner Perkins Internet Trends Report, Millenials who do become full-time workers value training and flexibility over pay. That means that, in order for companies to retain their best talent, they need to provide new challenges that allow for employee growth ALL THE TIME.

…in order for companies to retain their best talent, they need to provide new challenges that allow for employee growth ALL THE TIME.

Note that this is not just the millennial mindset. According to Roger E. Herman of the Herman Group, a group dedicated to analyzing and solving the employee turnover challenge, “Young people have always wanted something different than what their parents had. Today’s condition goes deeper, because the desire for change is not limited to young people. Practically our entire society is in transition.” (The Workforce is Changing How We Do Business)


Photo by Ruediger Theiselmann on Unsplash

People want a journey, not a job.

Let’s define a journey as an opportunity to both make money and (and this is the big shift) learn and grow along the way. It makes sense. If I am going to have to sell myself to get the next job, I have to be able to get better with each job that I do, thus coming out of each job a little stronger and more marketable than I was before.

So if you are a business owner, the question you should be asking yourself is, “What is someone who is working for me gaining while they are here?” Put another way, “What’s in it for them?” And business owners need to get out of the habit of thinking, “I’m paying them for the work. What more do they want?” Because the fact is, they do want more than that whether we like it or not. We can complain about that all we want, but the longer we complain about it, the further we fall behind.


There is an exciting part to all of this… for both the employee and the employer.

For the employee, a workplace that provides constant challenge and opportunities for growth keeps that employee engaged, interested and growing. If that employee ever decides to leave, he or she will be well positioned for the next job.

And here’s the good news for the employer.

If we are able to provide that kind of environment — one where employees are constantly challenged and are regularly growing — they are less likely to leave. After all, that is what they are looking for. AND our employees will always be getting better. AND if they do leave, they will speak about our organizations as places where people can go to grow.

That is what we want. We want to get a reputation for being the kind of place where people can go to grow. That will help with retention when we want to retain people and attraction when we want to hire new people.

We want to get a reputation for being the kind of place where people can go to grow.

So how do we create environments like that? How do we design a culture that is hyper-aware of the needs of its people so that we know exactly how and when to provide new challenges and keep our employees happy and healthy and growing?

We are not going to stop the new rhythm of the economy: employees jumping jobs every 2–3 years. That is here to stay until the next big trend comes along. What we can do is shift the way we build our arenas — the place and the way people work — so that we can attract and retain the best talent. That is the problem to solve in the first part of the 21st century.

Here’s your challenge: Analyze employee engagement at your company. Are people feeling challenged and engaged consistently? Are they being given new responsibilities regularly? Think about how you can feel the pulse of your people.

I’d love to hear about what you learn. We at CultivateMe are fascinated with the way people work now, the way people wish they could work and how we can build the bridge to the new world where learning and work are two parts of the same whole. Send me an email at doug@cultivateme.xyz.

If you’d like to learn more about CultivateMe and the way we are solving the employee engagement challenge, check us out at cultivateme.xyz.