// Internet Duct Tape

9 Ways to Know When to Jump Ship at a Startup

Posted in Startups and Business, Technology, Workhacks and High Tech Life by engtech on January 11, 2008


For the last couple of months I’ve been plagued with wondering if I should stay at my current startup. I’ve been approached with a few different job offers that I haven’t followed up on, and maybe it’s time I pursued greener pastures. In the words of the Clash: should I stay or should I go now?


Changing jobs is a big, life altering decision and if you have my knack for risk avoidment it can be a horrendous see-saw of uncertainty. It’s this state of uncertainty that is ultimately the cause of the most unhappiness in your life. Leaving your options open is always less satisfactory than making a firm decision.


When comparing offers from other companies, you need to compare the full package which is a lot harder than it looks.

  • Health benefits / Health insurance
  • Overtime compensation
  • Pension plans / Pension matching
  • Stock purchase plans / Stock discount
  • Stock options / equity
  • Travel allowance / food allowance
  • Raises

In particular it’s very hard to figure out what stock options are worth, if anything. The best advice I’ve read is that your stock options aren’t worth considering in any compensation comparison unless you are a founder.

This wiki page does a very good job of explaining how any employee can figure out what their pre-IPO equity is worth. What’s most important is to figure out the percentage of total options and how much funding the options are worth. Don’t forget to include capital gains tax (eg: 40%) when figuring out how much those options are worth.

More information on equity dilution

Business Plan

When will the startup be profitable? How much money has been invested in the company? How much more funding is needed until the startup can stand on its own legs? The more you can find out about this, the better off you’ll be, because you can’t accurately evaluate your monetary compensation and the future of the company without it.

At my previous job I was making more money than I am now, plus there was an average of a 5-8% raise per year. Startups often have no salary increases until they are profitable, or at least have revenue on the books. When you look at the roadmap to profitability you need to factor this in so you can evaluate if the potential payoff if the startup does well comes close to matching the potential revenue lost working at another company.


Most startups fail. The most likely outcome of working at a startup is showing up to work one day and finding the doors locked. There may be no compensation package for the newly unemployed workers until they land another job. Waiting for a golden handshake from downsizing is a worse idea than acting on an opportunity that has presented itself at a different company.

Technical Debt

Startups cut corners. You may not have the best tools available to get the job done. You are always squeezed for time and money, which means quality suffers. Poor quality can throw a monkey wrench into schedules, forcing crunch time in order to meet the delivery dates. This technical debt is just like any other debt in that it requires interest payments and you’ll have to pay it off eventually — although project managers often ignore it completely. Steve McConnell covers technical debt in more detail.

Signs of Success

Success should happen early. If things are always running smoothly then the work environment will be enriching and enjoyable. If things never work properly the first time then it can create a big cloud of doom that hangs over the head of everyone in the company and curses the new work being done.

Positive Reinforcement

How are employees reinforced for good work? In a startup, it usually won’t be monetary but that’s ok because one of the best rewards is the time to work on pet projects. Interesting work is its own reward.

Work Experience

Monetary compensation might pay off the bills, but it won’t make you feel as satisfied as a job well done. What makes me happiest is learning/improving new skills and knowing that I’ve done a good job. Having to constantly return to the same project that never works properly is one of the most soul-sucking experiences I’ve ever had. It’s like a bad relationship that drags on and on. You’re trying to make things work, but there’s always something new that comes up and drags you back into old issues that you thought were worked out a long time ago.

“Will I enjoy the work?” is the one of the most important criteria for evaluating a job change, because passion can’t be faked and it’s the only way a job will enrich the rest of your life.


Jeff hit the nail so squarely on the head when he said that the most accurate predictor of job satisfaction and success is if you like the people you work with. No matter what the problem is, it’s a people problem and if you don’t enjoy working with your coworkers then you’ll never enjoy your job.

Did you like this post? If so then please vote for it on digg. Thanks!

Related Posts