Is Your Career a Journey or a Destination? What To Consider as You Make Your Next Move

Samir Wagle
5 min readSep 24, 2021

A few weeks ago, I met with a client who was going through a career transition and wanted some advice. To protect his privacy, we’ll call him Michael.

After several successful interviews, Michael had two job offers on the table: one in the C-suite of a startup and one as an operating partner in a private equity firm.

Michael’s situation is not unlike the one that many workers are going through right now during this era of the “Great Resignation.” Even with a disappointing jobs report in early September, employers across the country still say that they’re having a hard time finding workers to fill open positions.

Before he considered changing companies, Michael spent time defining and creating the thoughtful blend of personal, professional, and social values that he wanted from his next position.

As expected, neither of his job offers ticked off every box, which led Michael to run into a mountain of self-doubt. Which offer should he choose? What if it was the wrong one? At the end of the day, should he just stay put at his current job?

As the founder of 11:11 Partners, I frequently help individuals and teams find the intersection of their skillset and passion — Michael was no exception. Before any candidate makes a career shift, here are three questions I ask them to answer before they make a decision.

Do you think of your career as a journey or a destination?

Imagine there’s a city called Dullsville, widely known as the most boring city in the U.S.A.

Let’s suppose I told you that you had to live in Dullsville for the rest of your life. How would you feel? If the city is anything like its name, you’d probably be pretty disappointed, right?

Now, let’s imagine you’re moving from Austin to San Francisco, and it just so happens that Dullsville is the perfect midpoint to break up the journey between these two cities.

In both scenarios, you have to spend time in Dullsville. But in the second scenario, a stop in Dullsville is just a stepping stone in the journey toward your final destination.

Thinking about a career transition shouldn’t be much different. We may like to think that we’ll be at a company for quite some time, but the days of being married to one workplace are long gone. According to a recent report from the U.S. Bureau of Labor Statistics, the median tenure of workers aged 55 to 65 is nearly 10 years.

For those aged 35 to 44, it falls below five years. And for those aged 25 to 36? The average tenure is less than three years.

Your next career move is unlikely to be the last time you switch jobs. Framing your career as a journey can help in deciding what you want out of your next move.

Are you giving yourself enough time to understand your objective?

The next step is to ensure you are in the right mindset and have given yourself enough time to think about your journey. When we hop into a new career, we’re often “running away” from a problem instead of “running toward” an opportunity.

People often believe that the most obvious problem in front of them is the real problem, which, in this case, is whether or not you should take a new career. The reality is that a new job may just be a new distraction. If we dig a little deeper, we may give ourselves the ability to contextualize and frame our problems more clearly.

To instill a new sense of focus in your professional and personal life, it’s important that you provide the time for reflection. Meditation, journaling, and mind mapping are excellent methods to create the space you need for a thoughtful evaluation of your path.

These aren’t quick-fix solutions. But finding acceptance in not knowing about what the future holds — and what letting go of an old career and starting a new one might mean for you — will allow you to think about your journey more holistically.

How will your next workplace get you closer to your long-term objectives? And what do you have to give the company in return?

To understand what you can get out of your next career move, you must ensure that your professional objectives fall under the factors within your control.

First, create career objectives that are SMART — that is, specific, measurable, achievable, realistic, and time-bound. For example, if your objective is to receive an annual salary of $6 million as a sales VP at a tech company by next year, your objectives are specific, measurable, and time-bound, but likely not achievable or realistic.

But if your career objectives are to be hired as a CFO by July 1, 2022 and to work hand in hand with a company’s veteran CEO to learn from her experience, your objectives likely check all the SMART boxes.

Establish these objectives early. When interviewing with a new company, you’ll be able to compare these objectives against the demands of the role. Simultaneously, your questions will help the employer understand your priorities. If the new position doesn’t fulfill your personal goals, then it’s not the best option for you.

And if they do, great — you’ve found the right option for you at this point in time. As an added benefit, these parameters provide important benchmarks to reference when the asks of the job change from what you need.

For instance, if your company goes through a reorganization and your responsibilities change, you might understand it’s time to leave based on your inability to fulfill your objectives. Leaving a job becomes much easier when you have a clear vision of your expectations.

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A few weeks after I spoke with Michael, he sent me a message.

After asking himself the above questions, Michael implemented meditation and morning pages into his routine in an effort to “really listen to myself,” he said. And his diligence and commitment to the practice made the job decision a relatively easy one.

He opted for the private equity firm in favor of the startup, citing a spot on the company’s leadership team for the business unit as important for his journey. The total compensation also felt better for his family.

Sounds like he’s “running toward” his next opportunity.

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Samir Wagle
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Founder of 11:11 Partners, Samir is an innovator with wide leadership experience in the consulting, retail, and hospitality industries.