I’m Not A Good Employee

Have you ever heard someone say “I’m just not an employee” or “After working for myself, I can’t imagine ever working for someone again”. I’ve often felt this way, even though I don’t work for myself (well, there were those two weeks).

When I started my job at HotPads back in October, I told my then-boss “I have to be honest with you – I’m not a good employee”. What I meant by this is that I hate to be managed by others. I want to explore this a bit more, because not everyone who hates to be managed can work for themselves. Sometimes, we must learn how to succeed as we are, where we are.


What Makes A Successful Employee?

Success as an employee hinges on both the external and internal factors of your specific situation. I’ve had jobs where I thrived because it was an entrepreneurial environment where taking risks and failing fast were encouraged. I’ve also had jobs where I was just told to follow instructions, and so I left pretty quickly.

In my current job at Zillow/HotPads, I’m leading online marketing on HotPads.com, where I have a team of 3 and hopefully soon 4. HotPads is a company that was bought by Zillow in 2012 and is still a small company (albeit almost 3x the size it was when acquired). As such, it is a very entrepreneurial environment. I lead marketing and help my team succeed, but I am also still a contributor and work on very specific and technical SEO and content issues and projects.

At the end of the day, my boss (who is Zillow’s chief marketing officer) gives me plenty of rope under which to succeed or fail. This is very similar to what Tom Critchlow did to me at Distilled, where he basically pushed me into the deep end and told me to sink or swim. I decided to swim.

To be successful as an employee when you are the entrepreneurial type, you must learn a number of skills:

  1. To take feedback well
  2. To push when you know that you are right
  3. To take responsibility when you are wrong or when you fail

Many people  don’t know this, but at one point in my life I was on track to become a commissioned officer in the US Army. Prior to that, while I was in middle and part of high school I was in Civil Air Patrol, which is the civilian auxiliary of the US Air Force. I’m also an Eagle Scout. Each of these organizations identified me as “leadership potential”, so they put me on leadership tracks and into leadership positions.

Unfortunately, “leadership” in these positions is less about inspiration and more about giving orders and expecting them to be followed. One could make the argument that even in these organizations the most successful leaders are the most beloved and respected. I’d agree, but orders are orders in the military, and breaking them is not accepted. Businesses are, I would argue, different in this respect.

When learning how to lead in the business arena, and to be led, I have had to learn that it’s not so important how you perform (though that is important) but how you respond to feedback and adjust to fit that feedback where merited. Not all feedback is good, but hopefully you respect your boss and they are there because they are experienced and good at what they do.

Being An Employee Can Be Hard

I’ve never been one just to take orders (hence why the military was a bad fit for me). I ask “But why?” way too much for that lifestyle. When people now are thinking about changing jobs and ask me for advice, I tell them to look for a boss who seems wiling to let you challenge them and do things your own way, with the understanding and trust that you will take responsibility for failures too. Take it from me – allowing this freedom to those you manage is hard. But ultimately it’s what many employees want and also how you succeed – by hiring people smarter than yourself and enabling them to succeed (hattip to Spencer Rascoff for that lesson).

Ultimately, We Are All Employees

If you’re a CEO, you’re accountable to your board, your investors, and every employee at your company. You work for them, not vice versa. If you’re an entry level person, you’re accountable to your boss.

I’m constantly learning how to be a better employee, ie to take feedback well, while also continuing to be intrapreneurial.

Do you have experience with this? I welcome your thoughts.

8 thoughts on “I’m Not A Good Employee

  1. Thanks John – Happened to grab this the minute you tweeted it.

    Edited this:
    If you’re a CEO, you’re accountable to your board, your investors, your clients and every employee at your company.

    Definitely the people I feel most accountable to as the top rung on our ladder is our clients. Not saying I don’t feel accountable to the others, but it feels as though (esp. in the SEO world) clients have the most to lose if unattended.

    I was also in the military and found that taking constant “blind” orders all the time was rough. I thought when I hit E4 things would get better, but even the E4’s took orders from the E5’s, 6’s 7’s etc. I had to get out at any cost!

    I’ve felt the same way about not being able to / wanting to work for someone else again. I got a taste for it 10 years ago and since then I set off on a path of doing whatever it took to work for myself even if I have to write content for a penis pump blog 🙂 (havent had to go there)

  2. Hi John,

    Interesting read.

    Do you ever wonder if being self employed would suit you better? Would you enjoy it more and not have so many of these mental struggles?

  3. Great post. You are awesome. I didn’t know you were in the military. And Eagle Scouts rule (I’m one too 🙂 ).

  4. Interesting read, Jon. I think what I like best about being a business owner is that for the most part, I control my own future. I don’t have to worry about my boss’ mood on any given day, office politics, helping other people’s numbers, or being pigeon holed into a specific set of tasks.. At the end of the day, I’m accountable to myself and my clients. Having more freedom and choices makes life more enjoyable.

    1. Hey Paul – Not to be down on Distilled at all, but yes. I have a lot more freedom at HotPads to lead. I think a lot of it is a function of being higher up in the company. I’m essentially the CMO of the HotPads brand, which means I get to make hiring and budgetary decisions. It’s a completely different gig from what I had at Distilled.

  5. I love working for my self because it allow me to take responsibility of what ever thing I will become in future

  6. I can relate to your points about feeling like a bad employee in the sense of not wanting to take orders blindly without asking why? I work both as an agency employee and as a freelancer and both have their own unique challenges. It’s very true that even when you are self-employed you are still an “employee” of your clients.

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