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The Side Hustle!

Feb 26, 2011

Posted Under: Tips & Tricks!

I recently came across this post How to Get Your Job to Pay for Your Side Gig on GenJuice, which instantly reminded me of a post I read quite a few months ago on Under30CEO – 15 ways to use your 9-5 job to start a business and the heated discussion around it.

As much as I loved reading both of these posts, I don’t agree with either. I second each one of the productivity tips that the “Anonymous” writer suggested in the article however, I would not encourage the young and aspiring entrepreneurs to utilize these tips to finish early with the day job and spend rest of the day on their side gig. Don’t get me wrong here! The post is full of practical tips that everyone should follow, only not for the purpose that the title & opening paragraph suggests. Just saying!

Similarly, while I like a couple of the tips in the other post, I still won’t suggest anyone to follow the rest of the advice there. Even if we totally ignore the personal ethics, honesty & integrity part of what’s wrong with this scene, to avoid who’s right or wrong and what should happen versus what does happen arguments, these tips for using your 9-5 to pay for your startup could be diabolic.

Here are a couple of reminders I give to my clients, who want to work a 9to5 as well as start something on the side:

Read the employee handbook! Well, skip to the sections that talk about employment exclusivity & relationship. Depending on your position, employment contract, company policies, and nature of your side gig – if caught, you may even have to hand over your side gig to your employer, simply because the employer owns whatever your produce/ create in those hours that employer paid you for. In some cases, the contract would clearly state that the compensation is for your exclusivity and comes with certain restrictions like – no business ownership, no part time jobs, or side gigs, etc all. You see, if you’re not a temp employee paid by the hour, the holidays, vacation, sick time, weekends etc all are part of compensation to make sure you are mentally & physically healthy to contribute 100% in those 9-5, 40 hours.

They are watching! Most HR & IT have access over almost everything you do behind the gray walls of 6X6 cubicle… They watch who is doing what, emailing what and to who, browsing what websites, making what calls etc. Plus don’t forget the office spies, gossip queens, and thin walls. If caught and you were let go because of “misuse/ abuse of company resources”, that would be pretty shameful and finding another 9-5 for paying the bills or whatever it is that’s keeping you there, would be pretty tough! What would you tell your prospective employers in the interview, why were you let go? Would your former boss still give a reference?

Now, enough of being the bad guy, the naysayer…

I did not write this post to discourage anyone from getting in the side hustle, in fact that’s one of the safest routes to escaping the 9-5 jail. I’ve done it, many of former clients did it and many of my friends and current clients do it.  I wrote this post to share my thoughts and forewarn every one of possible consequences. So what should the side hustlers do? Let me suggest some tips (& they all pass the integrity test):

Talk to your boss and get an informal green signal: As difficult as it sounds, this is the easiest and pretty much the only right way in reality. Here’s how you do it, first make sure you pick the right time, may be a time when you are getting some informal recognition for a job well done, may be the performance review time or just a casual coffee break. When would that time be, depends on your boss, time of the month/ year (if it’s a seasonal business), and most importantly your relationship with your boss. Prepare for the talk, make sure you don’t start the talk when you’re feeling the urge to, simply because you are angry at a peer or frustrated on something done a certain way in the office, because then it only sounds like a rant. Be prepared to answers questions like – why & how do you have so much time at hand when someone else in similar capacity is complaining about burdened with work? Why should you be given the special permission? Or what’s in it for the company? Be prepared for more tasks assigned from your boss, be prepared to justify why, be prepared to talk about your career & goals, and be prepared to suggest options (you dared to initiate this talk, might as well finish it with a solution instead of bringing it up over & over again)… Here are a few suggestions you can make depending on what you think would work with your boss and company (for example, if there’s someone in the team or office who’s already enjoying any of these arrangements, it gets easier to convince your boss). Assure your boss of the productivity and commitment towards the job and request him/her, if you can have an arrangement of:

  1. Come early, leave early: How about a 7am-3pm work day? So that you could have some interrupted time at work to be productive and most of the evening with a couple of business hours on hand for your startup. This one has the least compromise for the employer and hence is an easy sell.
  2. 4 days work week: How about 40 hours in 4 days? A weekday off in return of 10 hour long workdays for rest 4 weekdays gets them same amount of work from you and gives you one business day along with the weekend to better focus on your side gig.
  3. Telecommute: How about telecommuting/ work-from home? Promise them the 40 hours & productivity… This will save you the commute time and exhaustion as well as flexibility of taking occasional calls or replying super urgent emails of your startup, without feeling the guilt.
  4. Contractor or part time: If the first three don’t work, ask your boss, if you could be brought on board as a contractor or part time employee, with less 9-5 physical presence commitment and more deliverable based commitments.

If all else fails, you have two options: first, convince your boss that you’re fine with his/her decision and keep your eyes and ears open for “We will pay a lot of money if someone could do ‘__________________________________________’ for us.” This statement is full of opportunity juice! Can you be that someone who could do this for your employer as a contractor. Second, get a part-time job, with less responsibility and after-work stress, and resign from the current 9-5. May be an entry level/ part time position that you know would have least after work stress, so that you still have enough time & energy for your startup. This is a great way of keeping the cash flow in control, working on your startup, and staying social as well.

On a side note, here’s what I believe in – rewards are directly proportional to risks and efforts, if you put side gig efforts (evenings, weekends, some stolen hours from 9-5), it always will stay a side gig; if you don’t take the risk to face the uncertainty and give your side hustle, a fair shot full-time, it will always remain a side gig. Your call! Do you just enjoy working on one more project along with your job for some extra cash, or is it more than that? Please share your thoughts in the comments below.

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  • Hi Devesh
    Great article, you know I speak about this in my book, The Entrepreneur Equation. I would get a laywer involved to help you navigate what you are doing on the side.

    That being said, a side business (or jobbie as I call it) is a great way to test out the viability of a new business BEFORE you make the leap.

    • Thanks for the comment, Carol! Yes, having a lawyer’s help would be ideal!

      For those who find that as an expense or don’t want to spend a lot on hiring a lawyer, here’s an idea – “talk to your neighborhood lawyer or Law University students or Professors”.

      Carol, I’m half way through your book now! What I love the most so far, is the issue you raised of not having a particular screening process to be an entrepreneur, as other professions like medical, security, police, engineering, firefighting etc all, and your take on it.

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