How to Work Your Way Out of Corporate America Hell

Yes, this is a post targeted directly at some of my closest friends who are still tied down by the chains of Corporate America. I probably don’t speak to them often enough; it’s not because I don’t like them, it’s simply because each time we meet and begin talking, the conversation turns negative nine times out of ten. Why is this you might ask?   I personally don’t think I’m a negative guy. In fact, when I worked in “Corporate America” I was given the “Best Attitude” Award…ha ha! The reason things tend to turn negative, in my opinion (IMO), is because my friends know that what I’m doing as a self-employed entrepreneur is EXACTLY what they want to be doing…but they’re afraid to take the leap from that “security”. SECURITY MY EYE! It’s also because, due to the “chains” that have tied them down, there really aren’t a lot of positive things for them to share with me. In an effort to give you more than just my own biased opinion about self-employment, I reached out to some of the people I look up to in this world of self-employed freedom. Here’s what they had to say:
I worked as a consultant for two years, in those two years I saw my dress sense, hygiene, sleep patterns, health and body go to complete shit. I was working all the time I wasn’t sleeping, and I wasn’t sleeping enough, I would wake up and start working often without showering or dressing, often without having breakfast, never at the same time, I would order in and eat unhealthy foods, and I was almost completely sedentary. So my advice, have a room in your house that is a dedicated office space. Make sure you wake up at the same time every day and start work at the same time every day, make sure you have breakfast, shit/shower/shave and dress appropriately. Cook your meals, take frequent breaks and go for walks, do stretches, etc. Do everything the opposite of what I was doing. I was young and learned it the hard way. I was wide-eyed at the prospect of working from home but honestly, you have to pretend you’re not at home so you work smarter if not harder, work in an office space (don’t forget it’s tax-deductible), make sure you don’t let yourself get distracted by kids/wife/tv/anything else. – Muhammad Saleem To get all of the influential people in his/her life on board with the decision being made. You need to make sure that everyone understands the decision you have made, why you have made it, and that you simply can’t deal with detractors and doubters over the next couple of months/years. – Dave Mink In the words of Nike: Just Do It – make sure and have a plan though, set goals and work your ass off to achieve them. Leave all fear behind. There is no room for fear in self employment. Network. Use your connections and social media to let the world know what you are doing and how they can help. If you do, you will realize quite soon how much money you were losing by limiting yourself to a 9-5 … Be prepared for trials, but know after much adversity comes much success. – Mat Siltala
  • be out of debt
  • be willing to lose
  • have the funds to make educational “gambles”
  • be smart, if someone can do it better than you, hire that person to do it
  • stay connected with your market
  • be flexible
  • and work with your pants off
  – Paul Barker
From time to time I get to work with clients who are classic “Corporate America”:
  • They have to asked permission to speak in turn
  • They have to bring in 5-7 people to make simple decisions and get everyone’s complete buy-off
  • They have to use lots of acronyms and corporate “jargon” to sound more sophisticated
  • They use lots of cliches like “Win Win” and “ROI” and “High-Level”
Granted, there may be some “Corporate America” jobs that are to die for. But in my experience and in talking with many others, they are definitely few and far between. So what can be done? Gary Vaynerchuk, one of my favorite social media rockstars, shared this advice: The key concept you have to take away from all of this advice is you have to WORK; you have to WORK; you have to WORK! Continuing to work at your crappy day job and doing your self-employed dream on the side for a while is ok. But don’t fall into the trap of “someday I’ll take that leap” because that someday may never come. I took the self-employment leap over a year ago. It hasn’t been easy, but I’ve learned a lot of things. Here’s my list of suggestions on how you can take that leap and work your way out of “Corporate America Hell”…

The Hell-Hole Release Formula

  • keep working on your businesses while your at work (or before or after hours if that’s more safe)
  • set specific, measurable, reachable goals and HIT THEM
  • make a list of ALL your contacts
  • make a list of all the special skills you have that you can offer as services
  • set up a freshbooks account:
    • it’s a free invoicing tool that helps you keep books as you do work
    • it also has a timer to keep track of hours you’re working on projects
    • it took me a bit to figure out how to best use it, but now it’s basically something I HAVE to use to keep up on book keeping
    • it will save you money from paying a slimy accountant the beaucou bucks
  • use a tool like to keep track of progress
  • write out what you would LOVE to do if money weren’t an option
  • write out what you’d love to do for work if you could pick one thing
  • learn how to sell, sell, sell
    • EVERYTHING starts with a sale
  • Most Important Tip: go to all your friends who have taken the same path and ask them lots of questions (ie. insurance, accountant, tips, tricks, any partnership opps, etc.)
Thoughts? Suggestions? What do you think?

23 thoughts on “How to Work Your Way Out of Corporate America Hell

  1. Mat Siltala says:

    Thanks for having me on this Nate … I have never met with a successful person in business that hasn’t lost their pants (so to speak) … name of the game is to keep at it. Great post.

  2. Nate Moller says:

    @Mat Siltala
    Thanks for taking the time in your busy schedule to answer my questions. Thanks also for letting me be part of the DSM team and share my “clogging” and “Jimmer” skills with the world LOL. If it wasn’t for your help way back when (and on-going), I wouldn’t be where I am today.

  3. Mariah O. says:

    Great advice, Nate. My biggest issue working for Corporate America did have a lot to do with the business running people’s lives. I felt like even when I wasn’t working, I was still working because I was always thinking about what I needed to do when I got back to the office. Even on my beloved weekends. Jobs are great, but you gotta live the rest of your life as well.

  4. Chris von Nieda says:

    Excellent post Nate. I made the leap about a year and a half ago and couldn’t be happier. I have my family to thank for supporting my decision and riding the waves. 2012 is looking like a great year in the SEO business.

  5. Nate Moller says:

    @Chris von Nieda
    Yes Chris, that’s one thing I should have added – an ESSENTIAL thing – family support HAS to be there or you’ll sink the ship for sure. To get family support, I had to map out what I was going to do, how I was going to do it, AND have a back-up plan if things didn’t work out the way I hoped. I also had to show my wife the goals I had for monthly, quarterly, and yearly income.

    Thanks for the addition.

  6. Rosy Prose says:

    I started my own business 25 years ago and it was successful to the point where I had big office overhead, a staff, demanding clients,people to handle the IT and operations, bookkeeping, and all aspects of administration, a 401K and benefits for employees, etc. etc. etc. In short, I was working for my staff and clients,had more stress, worked more hours, lost my independance and was not having any fun. So I retired from that and now it’s just me and a computer and I’m in heaven! My advice – keep it small!!

  7. Mark Evans says:

    For me, the great thing about being a consultant working for yourself is being able to walk over to the computer at 3 am and work if you want to. Then, take the next day off without having to answer to anyone but yourself. As long as you are truly dedicated to your product and work, the rest to me is easy. After 12 years in business on my own, the excitement and danger of going out on your own as an entrepreneur keeps me on edge and hungry for revenue. And revenue checks made out to my company still give me a huge sense of accomplishment. I have no regrets about leaving the corporate world, and chances are I’ll live a lot longer. To all the good ole boy managers who got their jobs in the corporate world cause they knew someone not because of competence, I hope you have to go out and work for a living like everyone else. Unfortunately, most of you have already retired comfortably.

  8. rapid prototyping services says:

    After reading your post I can say no one can explain this thing better than you. Really good work you done here. Hope to see more good posts.

  9. Loc says:

    I agree with you 100%. I have a business which I do on my spare time that I just started but it is not generating any income (very little). Like you said Nate, it is a lot of work and can be very stressful at times especially if you have to work your 9-5 job and come home and do your business on the side. I hope the reward is worth it in the end.

  10. James says:

    In my opinion, the most critical point is being missed here. It’s not about “working for the man” vs “being the man”, it’s about your passion and happiness. To generically categorize those that have a corporate job as fools or sell outs is a mistake. My dad has worked in corporate America for over 40 years and has been passionate about his job the entire way. He’s approaching an amazing retirement and should be extremely proud of an incredible career. I have a friend that was just hired on at Back Country and absolutely loves it because, again, it’s what he’s passionate about. These guys have followed their passions and have never felt “tied down by the chains of CA” as you described. Not to mention, some guys just don’t have the risk aversion in their DNA to handle their own gig…that’s okay.

    In addition, I know many independent business owners that feel extremely “chained” to their business and long for the security of a corporate job. I guess what I’m saying is my advice to your friends whose conversations turn negative nine of ten times when talking about their “J-O-B” would be to leave and find something they’re passionate about…whether that’s their own business or something in corp America.

    The real irony here is that some day YOU will have a large enterprise with many “corporate America” employees. Where would we/you be without those that can get passionate about working in corp America? You have to love capitalism.

  11. Miele Callisto says:

    I have been self employed for along time and beauty of it is the FREEDOM that comes with it.Most people would love to be in the same spot but a simply unwilling to try it.People tend to need to be told what to do and are o.k. being restricted on how much they can make or what their value is. Just have a plan and execute it!

  12. Nate says:

    I totally respect your opinion but feel you should use your real name and email as opposed to a cover name and email. I heard this EXACT speech from one of my “upper-management” friends before I left corporate America for good. It’s funny how much your story resembles his.

    With much respect to you, I wonder why you hide who you truly are and would question how much you are called on to “hide” as a Corporate American manager.

    I agree that some corporate America jobs defy these rules and are wonderful places to work (just ask Costco employees and Zappos employees), but the corporate America jobs I’ve had (2 specific ones), feel into this criteria 110%.

    Best of luck to you.

  13. Brian says:

    I made that leap years ago, but it is very difficult without some money behind you. There’s many days Ive gone without food and its really just luck that has got me this far, which is still just survival level really

  14. Nate S says:


    Now that I am on the other side of this coin (doing my own thing), everything that was written, quoted, and implied in this article is absolutely correct! I think that one thing could be added… If you aren’t afraid to make the leap then there is a problem. A lot can be learned from coping with the fear and exercising the courage needed to put your best foot forward, and succeed cause you want to, because you NEED to. Go with the plan, stare at the opportunity with a “kill em all” attiude, and then DO IT!

  15. Nate Moller says:

    @Nate S
    Hey Nate! Thanks for the add on there – yeah, fear is a great thing if you let it motivate you to “getter done!” Although I do believe in a wise proverb that says, “If ye are prepared, ye shall not fear!”

    The biggest fear I’ve had to deal with is fear of doubting myself and my abilities. Sometimes fear of success can be an issue too. I know that sounds a bit contradictory, but it really happens.

    What are some of the ways you dealt with your fear and pushed through?

    (By the way, I went to the Dunes out past Delta last weekend on ATV’s and thought of you. I gotta get one of those soon!)

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