5 Thoughts for Career Crossroads

Ed Burdette
7 min readAug 27, 2019

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Normally, a career crossroads is something we’d try to avoid.

Maybe we were moving along in our career, doing our best to get along and keep our head above water. Work was hard enough as it was, and we didn’t want to make things more difficult.

Time passed, and even though every so often we’d wonder about other work, the steady flow of demands we faced kept us from really looking into our work. The work we are ‘called’ to do? That sounds very idealistic. How about paying the bills and getting through the day, day after day?

But then something happened. Maybe it was a failure at work, despite our best efforts to keep things together. Maybe our company began to struggle, or our whole industry changed, and our position disappeared as a result.

And so we found ourselves — at a crossroads in our career. This is the place we were afraid of, the place we tried to keep away. Standing here, we can feel some of that fear, mixed with resignation, uncertainty, and hope at what this could turn into.

Looking around, we see different roads headed in different directions. Which one should we follow? What direction should we take?

When our busyness is arrested, we have no choice but to stop and take stock. We have no option but to revisit questions that haven’t yet been resolved.

When we face a crossroads, here are five ways we can look around and begin to gain a sense of direction:

1. What is the Story So Far?

Maybe you’ve heard the expression ‘to understand someone, learn their story.’

This is true not just for understanding habits and any strange practices we keep; it also relates to the direction of our career.

A friend of mine is weighing the option of staying at his current job with taking a completely different position raising funds (and his salary) with a nonprofit he loves. As he considers these choices, he’s asking questions like these:

What financial factors are at play here?

What draws me toward each one of these jobs?

What is my life meant to say, and how could either option help me say it?

When at a crossroads, we may find that, from the perspective of job pay and position, there’s a tie between options — one way seems as good as the other. Bringing story-based considerations in can help break that tie and lead us in the direction we are called, based on the unfolding of our life up til now.

Asking about and knowing our story lets us see a bigger picture, and it’s in that context that we may well find insights for choosing the path forward.

2. Vision: The Preferred Future

My friends Bryan and Amanda were moving. After several years in a 1000 sq. ft. house with three kids, they took some time together to imagine the new house they wanted.

Would it have a dining table big enough to fit the family and several guests?

Would it include a ‘mudroom’ where people coming inside from the back yard could store boots, shoes, and coats?

Would there be a quiet corner where someone could sit and read?

As they considered specifics, a detailed picture began to emerge. They could start to really see the house.

One helpful question when we’re at a career crossroads is What do we want? This simple question, followed down to the bottom, gives us a start toward imagining what could become the vision we flesh out and pursue.

Here’s the idea with vision: it must be something that we’ll know when we reach it. Vision is an ‘intended destination.’ A crucial question in setting it up is: how will we know when we’ve reached it?

For Bryan and Amanda, this meant moving into a house with certain specific qualities. Their vision was clear because they could easily tell whether the house had those things or not!

For us, when we create vision for our work, we’ll want to be as specific as possible about what success looks like. The clearer we are, the shorter our path to getting there will be.

3. Where We Stand

Looking out into the future is a helpful step at a career crosspoint. Yet as my friend Gregg likes to say, ‘If we were in Colorado, but I thought we were in Missouri, and we wanted to get to Montana, how confident would you be that I could get us there?’

In other words, to get where we want to go, it’s important to know where we are! This is sometimes called ‘current reality.’ Current reality is a snapshot of everything in our life, positive oand negative, as it relates to our vision.

For example, if our vision is to write a 200-page mystery novel, then in writing down our current reality we would include things like whether we’ve written a book before, how much time we have to write, and how far along in the project we already are.

Considering our current reality regarding a career move, we would probably include our family situation, our financial position, work history, hobbies, and where we live.

It’s by doing a thorough accounting of our current situation that we gain the clarity to know how best to proceed toward a vision.

By engaging in this process, we may find that we’re farther from where we want to be then we initially thought. It’s good to discover this at the outset, because it protects us from missing our target later on. It keeps us from building a 100-ft-long bridge when really what’s needed is a 200-ft long bridge.

4. Resources to Make Change

Following along so far, we have two ‘points on the map’ — one is where we want to go (our vision), and the other is where we currently are (current reality). The next piece is to begin taking steps to close the gap between the two.

When we’ve given time to sharpen our understanding of both our starting and ending points, we find that steps to close the gap begin to emerge.

For example, say we have a simple vision: we want to throw an ugly-Christmas-sweater party. We’d like 15–20 people to come to our house, have snacks and drinks, and be part of a ‘secret Santa’ gift exchange.

Say further that our current reality is that our house can accommodate this number for a party, that we don’t have any special food or drink provisions in our kitchen, and that we know that weekends in December can already be busy with holiday events.

What steps will we need to take to bring our vision about? Based on our current status, we can see we’ll need to

* Make a list of who we want to invite

* Send them invitations, including instructions on the gift exchange

* Schedule the party for a weeknight to minimize conflicts with other events

* Make a list of snacks and drinks we’d like to offer guests

* Go shopping for those items a few days before the party

* Clean the house a day or two before the party

* Prepare a festive list of songs to play during the party

* Buy our gifts for the exchange, and perhaps a few extra for anyone who doesn’t bring one

With these steps written out, we can tackle each action one by one. When they’re finished, we’ll have done what we can to bring our vision into reality.

Regarding career transitions, the actions that emerge may lead us to train in a new area, reach out to our network for connections to new opportunities, or conduct an informational interview.

Different steps, but the process is the same — our actions stem from clarity around where we are and what we want.

5. Something from Outside Must Intervene

Notice that in that last section, there was space between doing all the action steps on our list, and actually bringing our vision into reality. In other words, it would be possible to do all those things and still not have the party we want.

We might send out invites but not get more than a couple replies back. There might be a storm the day of the party that shuts down power and we have to cancel. There are things we can’t control that nonetheless must happen for our vision to be realized.

With vision, this is always the case. There is always a mysterious separation between our best-laid plans on the one hand, and what actually happens on the other.

There’s a gap we can’t bridge. Complete control is outside our grasp. Ultimately, whether things happen a certain way is not up to us.

Rather than this being discouraging, or something negative, knowing it’s true can give us a healthy sense of release and freedom. We can gain a care-less-ness that’s good. Trust can start to grow.

Being stopped in our tracks at a career crossroad is not fun in the moment. But it can give us a ‘gift of interruption’ that sets us on a better road toward our calling.

Have you ever found yourself in a similar situation? What questions stood out to you at that time?

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