The worst vacation policy I've seen—and how to avoid it

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I learned the hard way about the importance of reading the vacation policy before accepting a new full-time gig.

Actually, it’s not even that. My mistake was even dumber.

I read the policy—I just had no clue what was acceptable.

After college, I attempted to build a few different businesses. The first was Shock and Yawn, “an online music magazine” with a focus on indie music. We made $8 in 9 months and I realized I had no clue what I was doing. I shut it down.

After that, I started a wedding photo agency, which did pretty well considering I really didn’t know how to run a business. I was making 30% more than any of my other fellow journalism graduates, plus I ran my own schedule and worked from home. Still, at the end of the day, it was a feast or famine job and I wanted security.

I applied to 40 jobs. After a grueling interview process, I got the offer.

I was so excited to get a secure paycheck, healthcare benefits and, most importantly, the chance to learn from others, that I would have signed nearly any agreement.

But I overlooked some landmines in the handbook.

For example, were I still working for that company, and I had taken yesterday (Friday) off, I would have had to take two total personal days. One for my vacation, one for the Memorial Day holiday that followed.

Yeah. They made us take vacation days for holidays.

This is total BS. But more importantly, it’s a red flag to watch for in the hiring process.

Ask the right questions

I’ve seen so many bad fits over the years. It’s taught me how to hire better, and if I ever find myself looking for a job again, I also know much more of what to look for when reviewing a handbook.

I didn't know what I was looking for when reviewing benefits. I was young and ignorant.

I learned quickly though—it did not take long to realize the vacation / PTO policy was horrible.

Once you’re aware of these kinds of situations and aggressive policies, you can sniff them out by asking questions around how the PTO works. Let’s review a few of the problems with my old company.

A few gripes:

• We got 7 sick days total. If you needed more, your pay would be docked (we were all salary…).

• No vacation for first year employees.

• We had to work 3 years before we got 10 days (effectively standard for all new employees with most companies).

• The worst part: If we took a vacation day in sync with a holiday, we had to also take the holiday. So if I took Friday before Memorial Day, I would also have to use one of my precious PTO (paid time off) days for the holiday.

• Zero vacations allowed in December (this was because they did give 5 company days off at Christmas although you were still on call). Still, it’s time you didn’t choose, and is also not very accommodating for those who may not celebrate the holiday.

• No more than 5 days of vacation in a row.

This is the worst vacation policy I have seen among a corporate setting. Most companies do better these day, but I'm sharing it to make it clear for anyone on the job hunt:

You deserve better.

If this is remotely close to your offer as a salaried employee, run.

I don't care how inexperienced you are, this is no way to treat a team. And had I known then what I know now, I’d have known it was a red flag for culture.

The company handbook was effectively telling us that our personal wellbeing and mental health was not important. I didn’t realize that. I was coming from working for myself—I worked all the time. Mental health wasn’t top of mind.

But the company’s attitude rippled out in other corporate actions, such as the annual “give back” day, where we were “donating time” to volunteer as a part of a citywide effort to get companies to give back to the community. The intent was to replace a day in the office with time volunteering for community service. Instead of using a work day, the company made employees come in on a weekend (I was slightly jaded at this point and just skipped altogether).

How I handle this now that I’m the CEO

Three of the GoWild founders worked for this company, and when we built our first vacation policy, we vowed to not only do better, but to lean into giving back as much as we can to our team:

• 3 weeks paid vacation out of the gate

• No BS rules around taking "contiguous" days to a holiday

• We do not track sick days

• If you need more PTO, that's fine. We track it to make sure you use it.

• We'll pay for your hunting/fishing/backcountry hunting license if you're needing it for vacation

• Take as much of your vacation at once as you want

Times have changed, but there are still companies restricting vacation time. Just know, if this is you, it's not normal or fair, and you deserve better.

And for the record, I am very anti "unlimited PTO." This has been proven to be a terrible system because employees don't know how much they can actually take, so they take less. Corporations know this when they roll it out, too.

When you’re on the job hunt, do not overlook these important policies. Ask questions. Dig in. And make sure you’re not only getting the right salary for your lifestyle, but finding a company that supports a life outside of work.

3 ways to evaluate a handbook

1) Look for landmines

You should expect at least two weeks of vacation policy. Dig into the company’s policy, and think through your goals over the next few years. After I was fired from this company, my wife and I were able to take a trip to Italy. The previous company’s 1 week policy would have kept us from taking such a trip.

2) Ask questions about flexibility

Great employees understand that if they’re a strong contributor, last minute vacations can hurt the team. They’ll be mindful about not dropping last minute requests on their manager. Still, make sure your new boss is forgiving because life happens, and sometimes you need mental health days or just random vacations. Our team randomly hit us with “I just need a day” and we give it—no questions asked.

3) Know the long term

When I was young and dumb, a few years to earn two weeks sounded find. But working 260 days a year without a vacation is insane. Working 520 and only getting five? Even crazier. Understand your long-term potential for your benefits and vacation policy, and know what is healthy for you.

Who I’m listening to: 49 Winchester

What I’m reading: “The Revolutionary: Samuel Adams”

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