Is it a bad job or just a bad day?

Five practical lenses to view the question of whether it’s time to leave

Nick deWilde
Jul 12 · 6 min read

There it is again– that nagging feeling that something’s wrong at work. Staring at the three-sentence email you’ve been writing for twenty minutes, you wonder if it’s finally time to hand in your two-weeks notice.

But doesn’t everyone have bad days at work? And what about all the good parts? You don’t want to quit reactively and regret it. So, how can you know if today is just a bad day or if you’re truly in the wrong job?

At Tradecraft, we often have conversations like these with our alumni. Whether they’re in their first job out of the program or their third, the decision to leave is never easy. If you find yourself in a similar situation, here are five practical lenses you can use to examine whether you’re in the wrong job or just having a bad day.

🧩 The Future Alignment Lens

A good job is one that prepares you for the job you want next. To figure out if this role is aligned with your career goals, try asking yourself the following questions:

  1. Am I helping the type of customer (individual, businesses, governments, etc.) I care about?
  2. Am I solving problems (access to information, transportation, health, etc.) that fascinate me?
  3. Does the type of solution we provide (software, hardware, services, etc.) interest me?
  4. Am I spending my time on activities (coding, designing, selling, etc) that I want to master?

Ideally, you’d want a role where you’re gaining expertise in all of these areas. If you find you’re lacking alignment in one or more of them, it might be time to think about a more serious career change.

If you aren’t sure what your career goals are, that’s okay. You can still confirm whether you want to continue down the path you’re currently on.

As a thought exercise, imagine getting a promotion.

Your boss pulls you into a conference room to share what a great job you’ve been doing lately. She’s been talking with her boss, and everyone agrees you’re ready for more responsibility and a title bump to go with it.

What’s your gut reaction?

Are you excited for the new challenge or dreading the thought of increasing your commitment? If a promotion sounds invigorating, it’s a sign that you’re on the right path. If you have no desire to take on extra responsibility, it means you’re either at the wrong company or on the wrong career path. To test which is the issue, picture yourself getting poached by the hottest employer in your industry.

How do you feel– excitement or dread?

Don’t worry if you don’t have immediate clarity on these questions. Replay them over the course of the next week and try to identify the emotions that are surfaced. These responses can you clarify your desires and goals before your rational mind catches up.

📈 The Progress Lens

Let’s assume this job is aligned with your future goals. A good job is also one that allows you to make progress toward those objectives. One way to measure this progress is through rate-of-learning. The question to ask is: are you building new skills and knowledge fast enough to justify staying?

To know whether you’re progressing at an appropriate rate, look at your calendar over the past month. What percent of your working hours were devoted to practicing and learning things that will be useful for the role you want next? 50%? 25%? 10%? Anything less than 15% should lead you to wonder if this job is the best use of your time.

Time-spend isn’t your only indicator of progress. Who you work with also has an impact on your professional growth. Returning to your calendar, consider the five people you spend the most time with at work. Are they strong in areas where you want to grow? Does their feedback help you improve? If you constantly find that you’re the smartest person in the room, it’s a good indicator that you should find a smarter room.

🌅 The Potential Lens

Beyond making progress toward your career goals, a good job is one that will continue offering opportunities for advancement. Here are ways to think about the potential of your current job:

  1. Is my company growing? — A growing company presents all sorts of opportunities to step up and try new things. Conversely, when your company is stagnant or shrinking in growth, you will likely need to spend the majority of your time doing the things you’re already good at (since these are the most profitable activities for the organization itself).
  2. Is my team valued? — Most companies have certain functions and departments that get favorable treatment. This can materialize in the form of increased budget allotment, better leadership, or opportunities for advancement. If you are on a team that isn’t valued, you may experience more resource constraints and limitations to your growth and influence at the company.
  3. Does my manager care about my advancement? — In order for you to grow within your company, you need a manager that is committed to your success. If you are in a situation where your relationship with your manager is tenuous, you have two options. One is to try to improve the relationship through feedback and communication. Alternatively, if the relationship has reached a dead end, you can try to switch teams or managers, though this can be challenging without support from senior leadership.

If you’re concerned about a lack of opportunities at your current company, start thinking about what you will need in order to advance at a faster pace, in the future.

👪 The Personal Lens

A good job is one that also aligns with your personal goals. While many employees have demanding jobs, these stresses, if taken to the extreme for too long, can have a deleterious impact on their health, wealth, and personal relationships. To uncover whether your job is responsible for unhappiness in your personal life, look out for these warning signs:

  • Your job is harming your relationship with your significant other
  • You don’t have time to devote to maintaining relationships with people who are important to you (children, parents, close friends, etc.)
  • Your job negatively impacts your health through loss of sleep or engagement in unhealthy habits
  • You come home from work with no energy

Sometimes the sources of these stresses are temporary and can be remedied. If your anxiety is the product of a specific coworker or your manager, you may be able to address the issue with a simple conversation. However, if you find that your stress is inherent to your role or aspects of your company culture, consider whether you’re getting enough benefit from the job to outweigh the toll it’s taking on your life.

⚖️ The Ethics Lens

A good job is one that empowers you to work within your own value system. If your success at work depends on your willingness to violate your own ethical principles, it’s not a good fit.

How do you know if you’re violating your own principles?

Try asking yourself how you would feel if your activities at work were explained to your parents, children, or published on the front page of the New York Times. While occasional violations may be easy to justify for the greater mission you’re on, repeated transgressions will impact how you view yourself and your ability to maintain relationships with others.

Before you turn in your two weeks notice…

Remember, it’s not always about you. You’re part of a larger organization that ebbs and flows. Some days you’ll need to take one for the team and absorb the stress of the company.

If you do decide that it’s time for a change, give yourself time to plan out your transition while you’re taking home a salary. By defining your career goals up front you will save yourself time and money in your job search and be better equipped to make informed decisions about the right role to take next.

If you need help with strategy or execution, Tradecraft has helped over 800 people transition into design, marketing, and sales roles at high growth startups like Airbnb, Away, Flexport, Lyft, and Samsara. Drop us a line if we can help.

Many thanks to Ariane Mohamadi for her editing help.

Tradecraft

Stories about startups, technology, traction, and design from Tradecraft members

Nick deWilde

Written by

Managing Partner @Tradecraft | Excited about building new channels for talent development

Tradecraft

Stories about startups, technology, traction, and design from Tradecraft members

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