At A Career Crossroads? 3 Exercises To Get You Unstuck

Today’s question comes from a reader stuck at a career crossroads. If you’d like to see your question answered in a future issue, send me a message ! For career coaching from a recruiter who has hired thousands, join my Dream Career Club .

I'm trying to decide if I should keep freelancing full-time or get a more traditional job with benefits, especially since I have young children. Thank you. - freelancer based in Baltimore, Maryland

You will face many choices over the course of a decades-long career : freelance or go in-house; pick one industry or another; stay in the same role or pivot careers ; take this offer or that one. There are also multiple factors at play and ways to decide. If you have clear priorities and a thorough understanding of each option, then a pros and cons analysis is straightforward enough.

However, if weighing the pros and cons results in a tie, or you’re paralyzed by the weight of deciding, here are three exercises to help break the impasse:

1 - Write out your competing stories

Find a comfortable spot, grab a journal or your laptop and settle in with a glass of wine, your favorite scented candle or other relaxing ritual. You’re going to move from sterile pros and cons analysis to a more freeform imagination exercise. Write the success story for each of your choices. What are you doing your first year, second year and as far out as your imagination can take you? What are you doing in a typical day? Who are you working with? What are you working on?

This Baltimore freelancer might write about their ideal freelance projects – types of clients, scope of projects, rates they’re charging. On the flip side, they would write about the ideal in-house role and what that looks like both day-to-day and over the years. If there are aspects you’re unclear about, take your best guess for now. You will want to research this eventually, but for now highlight these gaps to fill in for later.

The goal isn’t accuracy of how much you know about your career options because pursuing these details will interrupt your brainstorming. Right now, you’re trying to capture a feeling of what success looks like in the different paths you’re considering, and which path leaves you with the better feeling. As you do this exercise, you might find you don’t know nearly enough about one option (or both) to make an informed decision, so your next immediate priority is to fill in those gaps. Or, you might realize that there is one option you greatly prefer over the other, and the next logical step would be to focus on that option for now. You can always keep whatever work you’ve already done towards the other choice as a backup.

2 - Flip a coin

Heads you freelance; tails you go in-house. As the coin rises, notice what you’re hoping for. That inkling is a sign of your natural preference. When the coin falls, notice if you’re happy or disappointed – another sign. You don’t have to follow the coin, as it’s just an exercise, but giving yourself over to a coin toss is a quick and easy way to uncover preferences you might otherwise censor when you’re talking it over with a friend or even journalling in private.

Take the exercise one step further, and actually follow the result – at least for a while. If the coin says “freelance”, this means tabling your job search for, say two weeks, and only focusing on pitching projects. This enables you to drop the indecision for a while, which saves you drama and energy, and just focus on one of your options. During that focused time, see how far you get and how you feel. The uninterrupted test period may be enough to convince you one way or the other.

3 - Let the market decide

Pursue both options earnestly, and see where you get the most traction. This doesn’t mean you just accept the first job or project that comes your way. However, using real-time market feedback to guide where you place your efforts will help with a speedy search (which may be a priority for you). It can also prevent you from spinning your wheels in one place.

In Decision Time by Laurence Alison and Dr. Neil Shortland, one of the key decision mistakes people make is belaboring over a decision they actually don’t have to make. An example of this is wondering which road to choose – freelance v. in-house – when you don’t yet have either a project or job offer. You expend energy on the hypothetical decision rather than on the very real work of getting to the point when a decision needs to be made (i.e., getting an offer somewhere).

Start with feelings. Fill in the facts.

The above three exercises focus on getting you unstuck in this moment so you can continue the work of looking for your next job or project, and leave the actual take-it-or-leave-it decision till later. It’s about getting in touch with your natural preferences and feelings one way or the other, or least tabling those feelings, so you can focus and get more clarifying information. Once the feelings are dealt with (honored or tabled), you can focus on factual information – what is the scope of the work, who might hire you, etc. – and incorporate these important details into your decision. You may still get stuck again, weighing two compelling offers against each other, but at least you’ll have moved forward from where you started.

Caroline Ceniza-Levine is a longtime recruiter, career coach and founder of the Dream Career Club . She hosted the Land A Job You Love webinar, available to watch for free HERE .

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