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Transition Tips for Your Personality Type

Aug 10, 2023Aug 10, 2023

When it comes to military transition, the instructions should be so short, they could fit on the side of a coffee cup and read by your average terrier. It ain't that easy.

Instead, there are so many programs and so much advice on how to do transition right that you could drown in it -- and your little dog, too.

So how do you A) find transition advice that works; and B) find advice that works for you?

"That's the million-dollar question," said New York Times bestselling author Gretchen Rubin when I reached out to her recently. "People really want to be told the one right way, even when it is perfectly obvious that there cannot be one right way because people are so different from each other."

While researching her book "The Four Tendencies," Rubin found that how people react to inner and outer expectations can be the key to help them improve outcomes in so many stressful areas of their lives.

Expectations are a huge factor in military transition. I bet you are facing outer expectations from everyone from your spouse and family to your boss and the entire Department of Veterans Affairs. You also have inner expectations about what job you want to do, how much you hope to be paid and what you want to do for the rest of your life.

You may find that by paying attention to how you meet both inner and outer expectations and by altering your strategies accordingly, you can change the course of your whole transition.

Rubin divided people into four tendencies -- Obligers, Rebels, Questioners and Upholders. Look below to see a description of each tendency, what drives you crazy about transition and your best strategies to deal with it.

Upholders are those rare people who can meet both outer and inner expectations. You know you are an Upholder if you have worn out your Fitbit. If you stick to a New Year's resolution. If you still balance your checkbook.

What drives Upholders crazy about transition:

Unclear expectations. Nearly 200,000 veterans transition to civilian life every year. You would think that there would be one easy-to-understand, official, to-do list by now. But when you Google "military transition to do list," you literally found 147 million examples. How are you supposed to know you are doing the right thing at the right time?

Strategies that work for Upholders:

Applied contempt. It is so tempting for you to look at every list out there and decide you will do it all. Don't let yourself get sucked into the siren song of to-do lists.

Instead, Rubin (a natural Upholder) suggests that you pick a fixed number of lists you will look at closely. Find 3-5 examples from reputable sources. Pick more than five, and you can waste all your transition time reading lists) Use these exemplars to put together a master starting list for yourself. Then find the most skeptical Questioner you can to look at the list with you and decide which tasks are must do's, nice to do's or monumental wastes of your time.

To-do list ecstasy: Once you have your list, feel free to execute with vigor. Monitoring is a strategy that works well for Upholders. Keep track of your to-do lists on a spreadsheet or with an app and check them off as you go. Only let new things appear on the list if they are important and truly move you forward.

Transition appointments. Since your type responds so well to scheduling, make transition appear on your calendar as an appointment once a week. Do your transition work at that time and then put it away for the week, with the assurance that you have done enough. For now.

Questioners meet their own inner expectations, but they resist expectations from outside sources unless convinced it is worth their time. Questioners only need to look at the subject line on your email to figure out whether they will bother to read the rest of it. They question every aspect of transition to determine if it is truly necessary.

What drives Questioners crazy about transition:

Networking nonsense. Even though nearly all the research says that people find their jobs through networking, Questioners don't really believe it. The process is too nebulous, and the "strength of weak ties" sounds like a trick.

Strategies that work for Questioners:

Find the expert. Questioners are known for their ability to research and analyze. Since you are skeptical of networking, take the time to look up the research on social networks and jobs for yourself (and watch our free master class, Networking Without Awkwardness.)

By investing in the activities that statistically lead to a job offer, you will make your search far more efficient and effective than the competition.

Customize your networking approach. Most veterans and spouses start their networking with their close friends who are in the civilian world. Questioners don't like that approach because they hate being asked questions -- especially questions they don't have the answer to.

Customize your networking instead by starting with recognized experts -- veteran recruiting teams at the big defense contracting companies. Learn the right questions to ask them in our free master classes: Find Defense Contractor Jobs and Security Clearance Jobs for Veterans. Then when you have the answers, you can reach back to your friends and colleagues.

Cosmic clarity. "Analysis paralysis is a super big problem for Questioners," Rubin said. "There is so much research a person could do." In an area where there are 45,000 veterans service organizations offering transition help, the possibilities are endless. So many rabbit holes, so little time.

The strategy of clarity can come to your rescue here. Set out to determine what you plan to do for transition and why. "Dig, dig, dig," Rubin said. "Consider the opportunity from different angles: which jobs, which skills are required, how many openings there are. Once you have questioned enough, you will know if the path is right for you."

An Obliger responds well to outer expectations. They never miss a deadline. They will never stand you up. They can't bear to disappoint. But when it comes to inner expectations, Obligers don't do as well -- mostly because they put their own needs last.

What drives Obligers crazy about transition:

Fighting fires. The Obliger is so good at hitting deadlines and coming through for people that the command leans on them heavily. Obligers can get derailed by all the "shoulds" they face every day. No wonder you are not making progress on your transition.

Strategies that work for Obligers:

Hire a transition coach. Accountability is the No. 1 cheat code for Obligers. You thrive on oversight, deadlines and consequences to get things done. To make progress on your transition, you absolutely require the structure of accountability outside of yourself. (Spouses can't help here, because you think of them as part of yourself.) A monthly appointment with a career coach that you pay can provide the accountability and discernment you need to move forward.

Become the role model. Because you are respected in the command, other people notice how you approach transition and assume that is the right way. Resolve to model the right behaviors for others around you, so that they can have the best outcome possible. You are not only transitioning for yourself.

Deliver the treats. "Obligers feel immense pressure, more than other tendencies," Rubin said. That is why she recommends that Obligers give themselves a lot of treats during transition. Surprisingly, the treats are not rewards for getting your resume done or making a networking call. Treats are meant to energize you at a time you will be depleted.

"When we give more to ourselves, we can expect more from ourselves," said Rubin. Give yourself treats that truly energize you -- an afternoon at home on your own, a round of golf, a Sunday afternoon nap, a binge on the Marvel Universe.

When it comes to expectations, rebels have a maxim: You can't make me. And neither can I. Rebels resist both inner and outer expectations with extreme prejudice, even when it is something we want for ourselves.

What drives Rebels crazy:

Other people. The minute other people make a suggestion about transition, rebels must resist it -- as if resistance is their only weapon in a hostile world. Consequently, rebels often have a knee-jerk refusal to transition advice, even when it is something that might really work, like a job in Defense.

Strategies that work for Rebels:

Read hearts and minds. "The reason people are trying to nudge, remind and encourage is because they are worried you are not making progress on their timeline," said Rubin. When your stakeholders are pushing you, Rubin advises that you say something like: "I know I need to find a new job. Don't think I'm not paying attention. You need to let me do this in my own way at my own time." Then remind them of other times that you did come through as a good provider, responsible partner, loving parent and excellent contributor. Rebels place great value on being true to themselves.

Own your choices. When you joined the military, you knew that it would provide constant change -- new commands, new locations, new challenges. This transition to civilian life is something you knew would come eventually. You like fresh starts. Own your choice by embracing the transition as a time to emphasize freedom, choice, possibility and control through your actions. What do you want from your next role that you don't have now? Why do you want that? Who could you talk to? What would be your next steps to explore your options? How will I know that this path is leading anywhere?

In your own good time. When you have a knee-jerk reaction to an idea someone gives you (like a job in defense or government), resolve that you will let yourself come back to that possibility in your own good time. The more information you have, the more fulfilling your choices will be.

Also, when you do your informational interviews, resolve that you will hear people's suggestions as possibilities, not demands. Collect a lot of possibilities and then listen to your natural intuition as you guide. You could end up at an unusual post-military destination -- possibly entrepreneurship.

Oh, and IMHO, don't take a job with the federal government. Red tape will take years off your life, Rebel.

Military transition marks a major life change for everyone who has served in the military. Save yourself time and money by managing the way you meet all those expectations.

Jacey Eckhart is's transition master coach. She is a certified professional career coach and military sociologist who helps military members get their first civilian job by offering career-level Master Classes through our Veteran Employment Project and on her website Reach her at [email protected].

Transitioning military, veterans and spouses may be qualified for the job, but they are missing the secrets of civilian hiring. Find out everything you need to know with our FREE master class series including our next class You can view previous classes in our video library. Questions for Jacey? Visit our Facebook page.

Unclear expectations.Applied contempt.To-do list ecstasyTransition appointments.Networking nonsenseFind the expert.Customize your networking approach.Cosmic clarity.Fighting fires.Hire a transition coach. Become the role model.Deliver the treats.Other people. Read hearts and minds.Own your choices..In your own good time.