6 ways to redesign your career by letting go of outdated beliefs

What should I do with my life?

Jessica Tiao
Published in
6 min readJun 20, 2021

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Whether you’re exploring what you want to do next or you know the dream role or dream company you want to be a part of, this article is structured to give you practical steps towards designing your career.

1. Career ≠ job for life

“Job for life” used to mean you would graduate from college and work for a company, then retire. It meant loyalty. It meant a sense of pride. It meant a sense of meaingn and purpose.

Millennials — people born between 1980 and 1996 — have been labeled the job-hopping generation. While the data supports this, the tone of this societal discourse is outdated. We no longer live in the medieval era as knights where you swear your life to one overlord.

Let’s change the conversation: what if you didn’t have to find that one job that defines your life? What if you could think of your career in 2–3 year chapters, a series of tours.

You don’t have to figure out what the end looks like. Figure out your career one step at a time.

Source: Chuck Frey

2. Luck does not mean you need to be in the right place at the right time.

A research study showed that lucky people are open to opportunities. They prepare and develop skills. Good fortune comes from our thoughts and behavior. Move away from magical thinking and embrace a rational point of view towards luck.

Are you an opportunity generator? While you are nailing your day job, look left and right. Keep your ears to the ground. Stay insatiably curious.

3. Networking is not about using people.

In an episode of Veep, “Soulless Dan” networks with a first-grader.

Does networking feel sleazy or intimidating? Do you think of polished, selfish people who manipulate other people for their own gain? Have you ever met a networker where you could feel a sneaking suspicion that they want to use you?

If you think networking is tacky, let’s reframe how you think about it. For example, reframe networking is to imagine it as asking for directions.

Think back on a time when a complete stranger came up to you and asked you for directions. How did it make you feel?

You’ll likely feel a boost of happiness to help someone out. Think of asking for help finding information in a professional setting as though you are asking someone how to find the nearest cafe or ATM.

The goal isn’t to do the act of networking. The objective is to get your foot into the community.

4. Don’t look for jobs. Look for offers.

Have you scrolled through job listings for the perfect job before applying? The job descriptions are often a far cry from what the job really is.

How to spot red flags in job descriptions (original source)

You think, “Nope, not for me. I don’t want to work here.”

You might’ve ruled out a company or an entire industry or role after reading job descriptions, and your red-flag radar is ringing off the charts. The sad truth is that you’re either rejecting a position based on something you know very little of, or by the time you’ve ruled out bad jobs based on the job descriptions, there are too few options left.

Let’s reframe this by asking, “What interesting opportunities might this company/role be able to offer?” Look for offers rather than jobs. Be curious about the possibilities of each company/role rather than your preconceived notion of what it might be. Don’t look for the perfect position to apply for. Look for as many job offers with an open mind. When the offers start to come in, you’ll have more information to decide and negotiate from a place of understanding.

5. Informational interviews are not useless.

Most jobs are invisible. 4 out of the 5 jobs I have had in my career came from informational interviews; they didn’t come from job applications.

Here’s a template to ask for an informational interview:

Request for an informational interview request

Here’s the thing about informational interviews: don’t expect to get anything more than information. Don’t go into the interview expecting to get a job or to get introduced to a hiring manager. Offer to buy them a cup of coffee. Be curious, bring your questions:

  • How did you get your start?
  • What do you like about your career path?
  • What do you recommend for people who are starting out?
  • What are the significant trends or developments in their space?

At the end of the interview, thank the interviewer and set up an action item for yourself to follow up:

After the interview, send a hand-written thank you note (these are more memorable because most people don’t do this), or send it by email if you have the email.

Later, when you have something to share — an upcoming interview or maybe a job offer — send a note to your informational interviewer to let them know about your news:

If, after a few weeks, you get the job, congratulations! It’s time to follow up with another note. “I got the job, Jill! Thanks for all your advice.” The point is to be friendly, gracious, and helpful. Cultivate your relationship over time.

6. Stop giving your energy away; protect yourself from energy drainers.

This section is written for people who are tired of feeling tired. How can I stop feeling drained all the time? Is there anything I can do to recover my energy? And prevent this from happening in the first place?

This exercise is beneficial for introverts, INFPs who have trouble with protecting their energy. On a graph, plot out what is giving you power versus what is draining your energy:

Energy Engagement Map PDF by Bill Burnett & Dave Evans

Here’s an example of an engagement map:

After you’ve mapped it out, ask yourself: How can I rearrange my energy, so the levels improve? Once you identify how you can improve your energy levels, pace yourself.

Takeaways

When you’re feeling the itch to make a change, get curious, talk to people, try different ideas and tell your story. You don’t have to figure out everything or solve everything from the get-go. Set the bar low. Give yourself time.

Think of it as: I’m making progress, I’m learning, I’m going to meet new people, I’m getting out there.

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Sr. Product Designer @Twilio. Past lives: Crazy Egg, Kissmetrics, Tradecraft. Puppy and llama fanatic. Star-gazer. @JessicaTiao, www.jessicatiao.com