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7 Easy Steps (and 180 Sleepless Nights) To Becoming Your Own Boss

This is the true tale of my transition from corporate mid level exec jockey to mid priced self employed business consulting dude and largely the reason why the Donut Monday has been on hiatus the last 6 months or 180 sleepless nights. Large bouts of joblessness and possible financial ruin strangely dulls my humor. Only the names and the companies have been omitted to protect the not so innocent starting with yours truly who doesn’t want to get his ass sued as I recount my journey.

Step 1 – Get Fat and (Un)Happy In the Corporate World

You blink and all of a sudden you’ve been at one company for 13 years. You didn’t plan on it but you figure out how to not only survive but thrive in the corporate matrix. The pay is good. The benefits even better and the 6 week sabbaticals downright intoxicating. You think about leaving but they toss in Sr into your title. You think about leaving again and then they start calling you Director and that’s got a nice ring to it. Now it’s business class bookings on corporate travel and a cute admin. At this point you’ve dodged atleast 6 or 7 company wide layoffs so you think you’re untouchable or just damn lucky but who cares. You made it through the gauntlet and you start buying into the hype. But even though you’ve built up a dream and become a delegation superstar you’re in meetings 8 hours a day and 200 daily emails is a regular occurrence so you catch up at night after the kids are in bed a couple (every) night a week. Your friends start calling you a lifer and you think maybe they just might be right.

Step 2 – Buy Into the Start Up Dream

The dirty little secret is that living in the bay area can be a grind. So much wealth abounds and even though you’re W2 would bring bring no sympathy to anyone else in any other part of the country you start to feel like you settled and the house starts to feel smaller. And you’re about to turn 40. So you start to put out feelers on making a move to a start up , kick your feet up and wait for the offers to pile in like high priced veteran ballplayer who has just become an unrestricted free agent. But no offers come in. Sure you’re great, wicked smart and you put in the hours but you’re a corporate guy and you’re best years are behind you. You don’t know how to work in an environment without process. Can you sell the vision and close when the company’s existence depends on it? Can you work in an environment where everyone is 20 something and that salt and pepper hair is not helping things. No one tells this to your face but that’s what’s going on.

But then all of a sudden an offer comes in from a start up. OK it’s a start up that has been a start up for 10 years and you’re not feeling good vibes about the founder/CEO but then again every start up founder is a bit of a mad scientist so you talk yourself into this being the one. Who cares if it’s the only one. You take the job. The wife is supportive but starts to update her resume just in case.  The company is not based in the bay area so you become a temporary road warrior but you can handle it until you see the hotel reservation the company made for you and you think the one star rating is a typo. It’s not.  Business class is a long way away from your new home in row 39 middle seat. But you’re a seasoned veteran who knows how to play hurt and you soldier on. And before you know it you’re living the dream. Deals are closing. Attaboys and high fives all around. You start sitting in the quarterly board meetings. Your confidence skyrockets and you’re already counting ways to spend your forthcoming start up stock option wealth. Life is good.

Step 3 – Get Fired

While you are hitting nice strides in your job the revenue numbers come up short and your team members are getting picked off one by one. Rationale thought is in short supply and then one day the mad scientist CEO sets his sights on you and next thing you know you’re fired. I’m not talking about one of those prolonged individual performance plan layoffs with a soft landing and a fat severance plan kind of terminations. Or  the  sorry that risky new direction we took the company in didn’t quite pan out so we need to perform a mass casualty slaughter set of terminations. No I’m talking about a coming out of no where-in your face-made for TV-you’re fired-no soup for you kind of terminations transacted in about 15 seconds at curbside pick up at the airport by your boss who you were there to meet and drive to the big customer meeting that you set up. So now you suddenly find yourself curbside and jobless. And the airport cop behind you telling you to pull forward right afterward is not helping the situation at all at the moment. Curbside and jobless.

Step 4 – Have the Sure Thing Job Offer Fall Through

You know you had not been happy in this job for sometime anyway so the feeling of shock is quickly replaced by relief and ultimately joy because another large company had been recruiting you for a few months leading up to this moment. You were hesitating up to this point about going back to the corporate life but after getting virtually gunned down in broad daylight you start thinking maybe this start up life is not for you. Collect a severance, sign a fat offer and walk away unscathed. But just as you’re pricing out a 4 star family trip to Hawaii to celebrate the hiring manager calls up says the open headcount has been pulled but let’s talk again in 6 months and that’s when you really start to sweat.

Step 5 – Consume Large Quantities of Humble Pie

You’re a survivor so you shake it off, fire up the laptop and make LinkedIn your default home page. You punch out some key words in the job search that are representational of who you are and what type of role you are looking for. “VP”… “Team Leader”….”Superstar”.. “Generous Compensation”.  A few weeks later you’re resetting your expectations to “Entry Level”…”Flexible Hours”…and “Free Uniform Cleaning” It’s not going so well. You become a networking mad man. Lunch meetings are your daily ritual and while you put on a good face for friends and former co-workers who actually answer your email or calls no good job leads are materializing and you start to wonder if in fact your shit maybe does stink afterall.  You sit and your home office and do the job math. One unemployed single household income earner times  2.5  months average interview to offer time divided by 6 weeks left of severance to the power of end of season/holiday no one hires this time of year. Don’t forget to carry the one.

Step 6 – Reinvent Yourself

You’re on the 48th coffee meeting when a wise man asks if you’ve considered consulting. You had not. You’re a one company kind of guy but maybe it’s time to reinvent yourself. It’s 10am on a Sunday morning and there is an industry trade show Monday where you know everyone. 2 hours later you’ve booked a flight on your dime and 10 minutes before your local Fed Ex store closes you’re printing out the last batch of home made business cards. JSW Consultants is born. You’re on the 7th hour walking the tradeshow floor when in fact one of your former business contacts says they could use your consulting help a few hours a week. That grows to a few days a week and as you’re filing your business license, installing QuickBooks and pondering what exactly you can and can’t write off on your taxes in your new self employed status an email comes through on a new consulting opportunity referred by one of those networking lunch contacts you thought might be a waste of time.

Step 7 – Remake the Dream

Now it’s 6 months later and you have multiple consulting projects going at once, a few more in the pipeline and atleast 2 intriguing job offers, both of which you turn down for now. You understand the perils of consulting and realize there is no job security and it could all go away in less than 30 days but for now you’re not just surviving your thriving. You are the salary man who only knew one way to earn a living consciously took an unchartered career path and in the end learned alot more about yourself along the way.

5 Comments Post a comment
  1. John Wellwood #

    Very sobering and yet what a wonderful way to find the real opportunity of meeting and exceeding personal expectations.

    May 25, 2013
  2. Madeline Long-Duke #

    Scott, you are a great writer, very witty and candid.

    May 25, 2013
  3. Charlene Schill #

    This is such an enlightening description of the process you’ve been through. Thank you for that. It helps me understand what you’ve been through. I admire your courage, your skills and marketability as well as your ability to write so that others can really feel the experience.

    May 25, 2013
  4. Sheila Wellwood #

    Scott, I had so many laughs reading this epistle although I’m sure not so funny to you. I have always said that you are the most creative writer I know and I so enjoy your “Donut Mondays”. I love and admire you so much.

    Sheila

    May 26, 2013
  5. Reblogged this on sindyindah1996.

    June 2, 2013

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