How To Sabotage a Job Before Your First Day

Why in the world would anyone want to sabotage their brand new job? That sounds like a terrible plan. And yet, people do it all the time by accepting job offers that are not a good match for how they work or what they want from their career.

A few examples, with possible ways to avoid them:

Taking a job because you want “an exit”without guaranteeing that result.

There is no guarantee that a startup will achieve a large exit. Most startups fail. Even good ideas with good leadership. If you are OK with that risk, make sure the company is headed towards the exit you desire:

  • Ask in the interview what the end goal of the company is – if they say anything that does not match your goals, be wary of joining unless everything else about the job would make you happy if the exit never comes to fruition.
  • Read the employment contract carefully. Be sure your employment contract includes compensation upon any type of acquisition, including a funding round. Do not rely on the board of directors to watch out for your interests when making future deals.
  • Push back if the contract doesn’t offer what you need. You have a job offer in hand. They want to work with you. You can negotiate the contract without having to walk on eggshells out of fear of killing the deal. Ask for what you want – the worst that is likely to happen is they say “No”.
  • Do not over-value stock options. They are just as likely to be diluted away as they are to ever be worth anything.

Taking the first job that comes along out of desperation.

Know what you need from a job. Know what you want from a job. Know the difference. Make zero compromises on your needs. Go ahead and compromise on wants, with care – you probably want to spend at least a year or two in this job, so don’t compromise yourself into misery. Make sure enough of your wants are covered that you can get back on your feet without undue hatred of your work.

Be strong. It can feel reckless to turn down a job offer in your hand when you are desperate for work, and could start a job next week. It is tough situation to be unemployed with bills piling up and a family to feed. The need for work is real. But if this job offer doesn’t meet your needs, you’ll still be in a tough, miserable situation… just with more cash. You have traded one problem for another.

Taking a job that goes against your personal values

Suppose you get a great offer from a company that looks like they will give you the perfect environment, but it is run by leaders who go against your ethics, or produce products and services that run contrary to your personal beliefs. How long can you be happy spending 1/3 of your time each week working towards goals that conflict with who you are?

I recommend not even starting discussions with such companies. You’ll just end up having to decide exactly what your price is to break your own moral code, and either sell out or quit the job anyway.

This isn’t a life lesson you need to learn first-hand. Just stick to companies you can believe in.


These three examples don’t cover all possibilities. The first and third likely won’t even matter to the same people – mission-driven people often aren’t looking for an exit, and money-driven people often don’t understand the idea of working for a mission.

Those types of core personality differences are exactly the larger point, though – we are all different people with different goals, needs, and wants. And no matter what your goals are, some jobs will be a good match while others will be bad matches. Ask the questions while interviewing for a job to know which is which. And hold out until you find a good match.