How to overcome challenges in choosing your career

Updated 2023-09-08. Originally published 2013-09-06 on VocationVillage.com

bulletin board with career choices

There are common emotional challenges that happen when people try to decide about their careers. Here are some ideas about how to resolve those obstacles:

“Nothing looks right.”

Because there are no perfect possibilities, some people conclude all the options are terrible. This is a type of perfectionism. In addition, the U.S. workplace can seem harsh and unattractive, so I am not surprised when someone tells me they don’t see any good options because they see systemic flaws. I’m sympathetic to this, but unless you have a patron or trust fund, you probably have to earn a living. The goal is to find a choice that will not be perfect but will be satisfying and meaningful. I also believe if the work feels purposeful, it is easier to tolerate the inevitable day-to-day frustrations as all jobs have these.

“I’m interested in so many things, I can’t choose.”

Even though this is a good problem to have, it can feel painful. Decision-making in this case means deciding if you are a person who can multitask and build a “portfolio” career with lots of variety and different income streams, or whether you prefer to hyperfocus on one career area at a time. There is no right or wrong answer to this … the best strategy is the one that fits your brain and personality. It’s also important to defend your choice in a compelling narrative you can tell potential employers or clients so that your history makes sufficient sense to them they will hire you (for salaried jobs), become your client (for services-based businesses), or buy what you offer (for products-based businesses).

“How can I decide when there are options I don’t know about?”

There will always be options you don’t know about. First, there are 100,000+ job titles and those are just the traditional ones. If you count all the creative jobs that are composites of multiple jobs, the choices become infinite. You could never know about everything, even if you had a hundred years. To further complicate things, new careers come into existence all the time. Before 2023, how many of us had heard of “Prompt Engineers?” Choosing a career isn’t like shopping for a car where it is possible to know all the makes and models. The only way to manage the uncertainty of not knowing all the ever evolving career options is to move into a work environment where you will be one of the first to know about new paths. You can job shape to do something new if your skills and experience are adjacent to it, but first you have to join a professional community to be in the position to benefit from new choices.

“I’m afraid I will be disappointed.”

As long as you don't move in any new direction, you can keep the fantasy that there is an ideal career out there for you, but you just haven't found it yet. Once you make a real career choice, there will be good and bad things about your decision, which means facing a certain amount of disappointment. Therapy or coaching can help you work through these feelings and to learn to feel less dissatisfaction that it isn’t possible to find a career path that is 100% joy and 0% disappointment. Since all jobs involve some parts that are stressful, tedious, boring, or otherwise unpleasant, it is important to learn how to make peace with this, but to choose something that is worth it.

“What if I make a mistake?”

You definitely will make mistakes because mistakes are part of learning. There is no way to know in advance whether your predictions about yourself will come true. As you gain more experience, you’ll become better and better at knowing which situations are best for you, and you will be quicker at saying, “No,” to the wrong things. Everyone makes mistakes, so it would be better to make mistakes while learning than to make the mistake of inaction because of paralysis. It might reassure you to know that research shows people more often regret not trying something than trying and failing.

“I want mutually exclusive things.”

If you want entrepreneurial success with zero risk, that’s an example of mutually exclusive desires. It will never be possible to have 100% certainty and a guarantee of success when you launch a new venture. Another example of a mutually exclusive desire is seeking an extremely high income but wanting it immediately. I’ve never seen a “get rich quick” scheme that works. The goal with career decision-making is to decide what is MOST important to you, and which desires are secondary.

“No one ever taught me to make decisions.”

Some parents either didn’t know how to make decisions themselves, so they couldn’t teach the skill, or they knew how to make decisions but not how to give up the control of letting their child learn to make decisions, too. This causes a situation where an adult lacks the essential skills of adulting. Some coaching clients have the fantasy that a coach can tell them which career to choose. No one else can make the best life decisions for you … they can only ensure you have all the tools you need and the support to navigate the decision-making process.

“I feel worried all the time. Or sad.”

You may come from a family environment where anxiety, worry, and/or sadness are the dominant emotions. You may have a personality that is prone to anxiety or depression, and you may have to work harder than other people to feel peaceful and optimistic. That’s okay … even people struggling with fear or depression can learn to feel more centered and confident. If you suffer from clinical anxiety or depression, these are treatable disorders.

“I know what I want, but my family won’t let me do it.”

Your family may be well-intentioned but convinced that the only way you can be happy and successful is to pursue something they picked for you, usually something like engineering, accounting, medicine, or law. The problem is that other people’s dreams for you might not be in sync with your skills, interests, and values. Trying to follow someone else’s preferred path can be like trying to hold a beach ball under water ... eventually it will probably fly into the air. If you need help to set boundaries and achieving more autonomy without losing valued connections, a therapist or coach can help you find the right words and feel sufficiently supported to say difficult things to the people you love.

“This process of choosing a career is overwhelming and lonely.”

I know! That’s why I recommend professional therapy or coaching. It’s always easier to do challenging things when you have more support.


Do you have questions about your career? If you send me a coaching question, I may select it for a response for a future article.

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