Looking for a new job? Here’s what holds you back.

Photo: Bethany Legg — https://unsplash.com/bkotynski

Around 75% of the people reading this are open to or looking for a new job.

As we consider the next steps in our careers — whether we want a different role inside our current company, a similar job at another company, or are moving into something entirely new — many of us hold ourselves back by:

  1. Waiting until we’re 100% prepared before taking any real action (e.g. spending weeks perfecting our resumé rather than contacting a hiring manager)
  2. Paralyzing ourselves over choosing the “right” decision rather than embracing that careers are a series of small steps (e.g. agonizing over whether to enroll in an MBA program before having spent a day working in an office)

Let’s explore both in more detail.


Mistake #1: Waiting until we’re 100% prepared before taking any real action

Careers are not about prepare prepare prepare until – AHA! — one day you are ready.

Even if you earned your MD yesterday, you may never feel fully prepared as a doctor. Your credentials confirm levels of expertise and experience that are crucial to doing that job with the required level of mastery. You have proven your skills enough to legally treat patients. But preparedness is more about one’s state of mind.

What’s better than being fully ready is to prepare just enough to get started (with professional oversight if, as in the case of medical care, it’s your ethical duty).

Everybody feels like a phony to some extent. Some take action despite that feeling, while the rest of us wait until everything is perfect. Which, of course, nothing ever is.

Whatever job transition you’re considering, that next role will meet some of your expectations while failing to meet others.

You can’t predict everything in advance. Avoid the urge to over-prepare or you risk wasting time learning things that have nothing to do with the job. Instead, if you prepare just enough and approach the role ready to learn, you’ll be more open to novel solutions. Your mind won’t be cluttered with pre-thought, textbook answers or years of learning things the ‘wrong’ way. That keeps your thinking rigid and narrow. So embrace your beginner’s mind and stay open to whatever surprises come your way.

This also helps to avoid perfectionism. Your resumé or portfolio will never be “ready.” Whatever job you seek, someone has most likely found themselves in a similar role with a portfolio sloppier than your own. It won’t help you until someone sees it.

Get Repped

A creative director friend of mine has been working for the past few years to become a TV comedy writer. Let’s call her Morgan.

Nah. Let’s call her Jill.

Jill is hilarious and extremely proud of her four pilot scripts. She has run them by dozens of people in her network, which consists of current and former TV writers, producers, showrunners, etc. These scripts are as polished as they’ll get.

But none of her shows will never get made — nor will she become a staff TV writer–until she gets a talent representative to find work on her behalf. Without a rep, she’ll forever fend for herself and will likely be taken advantage of by a bizarre industry that plays by its own rules. She’ll always be spending her time and energy on things that are out of her element, chasing jobs and trying to make deals rather than writing.

With a rep, whose entire job is to get find her writing jobs, Jill could focus on what she does best: observing life and using it to write dark, funny, thoughtful TV shows.

Yet even though she knows a talent rep is the crucial next step, Jill is not yet willing to take meetings. The scripts aren’t quite ‘there.’

That is, they weren’t quite there until she and I met yesterday to talk about this. In that conversation Jill realized that her high standards and perfectionism have been delaying her TV career. I got pretty fuzzy inside when, after we said goodbye and were walking in opposite directions, Jill turned back and yelled, “You’re right! I just have to do it! I’m gonna go make some calls! AHHHH MOTIVATION!” before running away.

Now, I am not discouraging you from polishing your resumé, website or portfolio. It’s important to feel confident that any material you present is a solid reflection of your best work. It’s also wrong to spam a bunch of hiring managers with your LinkedIn profile. Don’t be lazy. It shows.

My message here is that we need to be aware of the trap we’ve all experienced where we spend months tweaking the font on our resumes rather than writing a few emails to someone who might actually want to work with you (despite your love for heavy, serifed fonts).


Feedback Rules

Another way around this portfolio perfectionism is to ask for feedback on a project that is in-progress. Say something like, “I’m working on this new infographic. The layout is still a bit messy, but the content had some insights I thought you’d find valuable so I didn’t want to wait to pass it along. If you have any thoughts or feedback I’d love to hear them!”

This shows that you

  • are working on something important
  • trust the person enough to value their opinion
  • care about the quality of your project (you are being open to constructive feedback)
  • understand their needs as a potential client or employer, because you have identified something that would be of value to them

In fact, this process can serve you even better than a polished resumé. Getting the other person involved in your project by reviewing your work turns potential employers and clients into partners and collaborators. They’ll get a chance to see your enthusiasm and learn how your mind works. Plus, now that they have participated in the process, they have a stake in your success and won’t want to see you fail.

I started my video editing career without a video reel and a coaching practice without a website or any clients. Had I waited until I had the perfect reel or site, I never would have begun. Even though I struggled with perfectionism like anyone else, the few people I did reach out to before I was ready ended up being the key to those careers progressing. Otherwise I would likely be sitting here, years later, still changing the colors on my website without having really worked.

Ok. We know that because you’ll never be ready it’s important to start reaching out now.

What about that second point?


Mistake #2: Paralyzing ourselves over choosing the “right” decision rather than embracing that careers are a series of small steps

Especially if you want a role that requires new or different skills, don’t expect to wake up one morning “ready” for the job.

Yes, you may eventually wake up with a new title or responsibilities that you didn’t have the day before. If you go through law school you will probably wake up on day as an Attorney.

But it’s in the years-long journey up to that point that the real shift takes place.

So if you are considering a job or career change, think about what you can do today to get started on that adventure.

Try things out. Find some people doing what you want to do and schedule an informational interview. Shadow someone. Instead of spending years getting an advanced degree, see if you like the life that degree would provide to you by asking some people in that field. Work for a day in a different department at your company. Help out on administrative tasks, if only to experience what life in a different role is like.

Our careers change over time, not overnight. We must get some ideas of the direction we want to go, and then take consistent action in that direction.

But don’t simply decide on a course and charge forth with blinders on.

It’s important to notice the tastes and smells so you can course correct along the way. If things smell fishy in one direction, shift your attention elsewhere. If an opportunity looks interesting, go after it. Touch it. Examine it from all angles.

I worked with someone who wanted to get into video production. She was working in finance at the time and felt she had no opportunity to be creative at work.

So she started talking to people in the broadcast production world, meeting with folks who were living the production life in front of and behind the camera.

After two weeks of exploring she came back to me and said, “Yeah, uh, I don’t think I want to be in production. It looks really cool and sounds really cool on paper, but it’s SO stressful, the hours are insane and I would never have a life.” Two weeks of research was far less costly than going to film school simply because the film industry sounded ‘cool.’

How, you may ask, did she solve the original problem of expressing herself creatively at work?

Those two weeks made her realize just how much free time she already had. Her 9am-4:30pm job allowed plenty of time after work and on weekends to write and take photos. She also discovered that, for her, being creative for a living would take most of the fun out of it. She was better able to work on — and enjoy — her creative projects when she kept them separate from work.


Explore before you jump.

Say you have always thought about getting into interior design and are thinking, “Ugh, I wish I could just become an interior designer. How can I do it already?”

First you need to explore whether it’s the right path for you. Find a designer you admire and reach out to them. If they don’t get back to you, find another and reach out to that person. Ask what they like most about their day-to-day, what keeps them up at night. Ask them why they get out of bed in the morning. Ask them what they would have done differently. Then see how their answers match up (or not) to your prior expectations about that job.

If it still sounds interesting, ask the same questions to a few more people and. The truth of what life is like as an interior designer will reveal itself as you begin to see patterns within those different perspectives.

If it’s still interesting, start the shadowing process, research professional skills and certifications required, and so on (if you need help from there, consider hiring a coach).

But what if you want a new role in your current company that’s drastically different from what you do now?

Again – don’t wait. Start now!

I worked with an individual who was a senior producer and for years wanted to move into the creative department. She had plenty of success producing, making deals with artists, scheduling and managing budgets. But she has a great artistic eye and was eager to get more hands-on in the process of designing and writing commercials.

For four years she jumped on every opportunity to flex her creative muscles in and out of work. She enrolled in night classes to build her skills and developed relationships with creative directors. She even stole real-world client assignments that were not meant for her– and took them as her own assignments.

At one point she sent some of those ideas to the creative leadership for feedback.

Turns out she had gotten pretty good over the years and her work caught the eye of a creative director. In fact one of the assignments that was based on a ‘stolen’ brief was so impressive that it landed her a job!

This person did everything right. She realized that to build a solid portfolio while working another full-time job she would have to be clever. So she took here career into her own hands by:

  • finding her own assignments
  • communicating with decision makers
  • soliciting feedback
  • being persistent

This took work. Four years of work. But it was well worth it for her to spend the next 10–20 years on a career path that makes her jump out of bed in the morning.


We’ve outlined the traps of over-preparing and perfectionism, learned the value of feedback and immediate action, and know how our path will only begin to emerge after we’ve taken the first step.

A few key takeaways:

  • you’ll never feel ready
  • nothing is every perfect or ‘complete’
  • since nothing happens all at once, the best you can do is get started now with the information you have
  • pay attention and adjust course as necessary

Now, in the spirit of taking my own advice, I’m going to hit Publish even though I don’t think this article is 100% done. I do hope you have found it valuable and would love to hear any feedback you may have.

Good luck out there!

Austin