Living a Startup Double Life

Managing your startup project while staying employed full-time

How did you get into this mess?

You’re an office monkey in a Fortune 500 company, making “a real impact with your work”, as your manager feels necessary to assure you during your annual performance review; you earn a decent salary, regularly get your hand shaken by senior executives and every Friday is Full-English-Breakfast day! Life should be fine.

Hell, it’s not like you have to wipe elderly asses for a living.

But you still wake up every morning with this feeling that you’re living the not-quite-so-good life, increasingly turning into more of a can’t-take-it-anymore life.
You just know deep down in your belly that, for all the benefits of this secure and well-rewarded job, which most people would see as a successful career in its middle stages, you can hardly stand another day of it.
Something is wrong, and — like a man trapped in his burning house — you desperately look for an open window through which to leap to freedom.

So you start reading. You have followed startup stories and small business ideas online for some time and you are starting to generate ideas. It never takes long to find a few which seem viable and eventually you probably settle on one that is either close to your current job, making use of your existing skills and the experiences you gathered in the corporate world, or one which is related to a hobby or passion you've been developing for a while.

You have a plan, you know what needs to be done, what the project will take, how to start… but there is one problem: You have no money.
Or at least not enough. The ideal scenario of quitting your job and living off of your savings until your side project generates something of a salary is a distant utopia to you. A year or two ago you didn't know that you would need a big pot of gold now. You never actually got around to implementing a real savings plan which would be large enough by now to pay your bills for six months or a year. And let’s face it: Your family and friends would probably help but unfortunately they neglected to become millionaires themselves and you've got bills to pay that go beyond basic rent and food.
“Thanks for allowing me to install a Google Fiber line in your basement, mom. Do you think you could buy some new clothes for my wife and kids sort of soon-ish?”

You've got no choice: You need your day job to finance your new startup night job.

So what do you do after binge-watching Breaking Bad the whole weekend following this realization?
You start re-organizing your life, that’s what.

You will face three devils.

1. The Obvious Lack of Time.

Between an official 9-5 day job (unofficially more like 7 to 7, amiright?) and basic necessities of life such as sleeping, never mind eating, it’s going to be tough to be productive for your new venture.

Here are a few tips to make sure you get the maximum time available to work on your new business:

Optimize your day job!

In order to not work too much overtime, make sure your daily activities in the office are being done as efficiently as possible. Start by scheduling more: Use whatever calendar, task manager or other tools you can exploit to their full potential, to enable you to work according to predefined time slots and reduce ad-hoc activities to a minimum.
If it’s feasible in your role, make it clear to your boss that, unless you get to take any of the overtime you’re currently doing off later, you won’t do it any longer. Do whatever you can to leave office on time and not a minute later.

Delegate if possible and reject urgent work that cannot be scheduled by pointing at your already full calendar (you can re-prioritize if needed, but then something else needs to go).

Try and finish as much of your daily work as you can in the morning, in order to free up some time towards the end of the day (without publicizing that fact to your boss or colleagues). You can then safely spend some of that freed-up time to “mind your own business”, as Robert Kiyosaki would say.
Yes, technically you’d be doing private stuff on company time, but if you have already completed the work that is expected of you, you shouldn't feel guilty about that.

Next, make sure your time spent on the new business is organized effectively as well! This will depend on your specific circumstances and the type of business you’re working on. But the idea is to identify what work needs to be done when, and not waste any of your precious time by doing too much too early or the wrong thing entirely.

For example: Writing a business plan? Don’t believe the old-school hype. It’s really only good for one thing: To get outside funding. If you already have the funding you need, you can be very flexible with the paper work. In order to organize and formalize your business idea, a simple one- to two-page Google Docs paper with the basic structure of your vision and an abstract timeline of what you want to achieve at which stage of the project, is really all you need to get started. You will necessarily refine and flesh out details later, and you are the best judge of how much up-front planning is really needed before you can begin taking your first steps. Things like market research and product mock-ups are much more useful and urgent in your initial stages!

2. Avoiding Distraction.

You know these days: You’re working on this super important project, which is so complex and so critical that you think about it all the time even after work: on your way home in the evening, during dinner, you even dream of it until the morning when your first move is to check for new emails. This has to stop!
Draw a clear line, create a routine that lets you shut that noise out as soon as you leave the office and won’t let it back in until you step into the office in the morning. Maybe go to the gym, exhaust yourself right after work, read a few pages of a captivating novel or have a good conversation with your child about their school day or with a friend about Ice Road Truckers.

In the morning, do not check emails until you’re in office! I’m dead-serious: unless it is part of your job description, don’t even look at your phone after waking up, during breakfast or while sitting on the train. Use that time instead for private things, conversations with family members, reading a few more pages of that novel (make sure it’s fiction, don’t fall into the trap of picking up a non-fictional book that makes you think too hard).

Whatever it takes to get your mind off this work nonsense and let’s you start the day fresh and unburdened. From now on work stuff only matters when you’re at work. It has no value for your private life or your new business so shut it out whenever you’re not there!

Family and Friends should be aware of your new project. You want to avoid disappointing them by declining invitations too often, so explain to them what you’re doing and make sure they understand how important it is to you. Make no mistake: Your social life will suffer! If you’re working a full-time job while also starting a new business on the side… something’s gotta give. That is not to say you shouldn't make some time, especially for close family, but you need to be able to dedicate time to your startup after work, and just like in the office scheduling can help you here as well.

Whatever scheduling tool you prefer to use, make sure it starts when you wake up and ends only when you go to bed. Plan and timebox everything. If you have a family, agree with them what part of the day will be your dedicated startup time. You know… Kids go to bed at 8, then you have a dedicated startup time slot until 9:30, and the rest of the evening is spent with the wife or maybe another hobby etc.
During that dedicated time slot, remove yourself from everything and everyone else! If you have a home office, lock the door or make sure everyone knows not to disturb you. Otherwise go to Starbucks or a pub with free Wifi and work over a coffee or a beer. In fact, getting out of the house is usually better, even and especially if you live alone. But that’s up to you. Also apply all the usual tactics to minimize distractions while working: Make sure you don’t browse social network sites (unless your business requires it, of course), don’t watch TV, don’t chat with friends on messengers… You’re an office worker, you know exactly what I’m talking about!

3. This nagging Death Wish

Your early stage will be wrought with fear and uncertainty. You don’t know whether this is going to work out, you don’t know if it will make a single penny, you are afraid you’re wasting your time or that you are forgetting something important, or worse: you don’t even know whether there’s something important you should be doing instead of still tinkering around with code or correcting typos in your oh-so-thorough business plan.
Later on, as you learn more and details get fleshed out, you will become more confident about what you’re doing, but the stress of keeping up this double life is seriously gnawing at your knees.

Basically, throughout your project, from the first idea through to go-live and the first growth push, you will keep hearing these voices in your head that tell you to just give up and go back to your old life.
Everything was so much easier back then. Is it really worth it all? You see your family and friends starting to get worried or angry even. Your health starts to get affected, you’re constantly tired, eating too many takeouts, neglecting your workout… What the hell are you doing here? Are you crazy? You’re going to fail spectacularly and you will deserve it, for being such a fool to run off on this random idea you had in the shower one day!

You need to resist these voices! There may well come situations when cutting your losses is the right way to go, but these decisions are driven by rational and well-considered analysis!
Tiredness, a reduced social life, self-doubts and fear… none of these are valid reasons to turn around and give up on your dream!
One, because they are just emotional resistance which tell you absolutely nothing about whether or not you can or cannot succeed.
And two, these are the kind of problems you can actually do something about. They are not brick walls mounting up into the sky in front of you. Market research that proves your idea will have zero demand, unavailable funding, not getting access to a death ray satellite… these would be examples of such a wall.
No, these emotional hurdles are only there because of how you approach this whole thing, and there are ways to overcome them:

Overworked, constantly tired? Rearrange your schedule, reduce your dedicated startup time slot, maybe give yourself one or two free days a week, go to bed earlier, dedicate more time to relaxing activities etc… The internet is full of advice for this kind of thing. Remember that you don’t have to have a fixed deadline for your go-live, certainly not if your health is the price!

The fear of failing is getting to you? You feel you don’t know what you’re doing? Well guess what, no new startup founder ever does! It helps reading founding stories from other people, engaging with them if you can. You will quickly find that every first-time startup creator had to take adversaries as and when they arose. No one anticipates everything and you will hear from every single one of them that the experience needed to succeed in your business is a post-factum thing: Learning by doing is basically part of your job description.

Visualize your worst case scenarios. What really is the worst thing that can happen? That alone will ease your mind, weirdly enough, because it’s never actually as bad as it feels when you haven’t thought it through. Maybe you can even plan for that scenario, mitigate the risk somehow, just in case?

Know that all you can do is make a start with whatever knowledge you have, having done all the research you can think of at the time, you simply get the ball rolling while keeping an attitude of constant learning and adapting flexibly to new circumstances… everyone else did it this way, so you will be fine as well, I promise!

As mentioned above, networking with others who have gone down a similar path will definitely also help you avoid some nasty traps, and at least turn some of your “unknown unknowns” into “known unknowns”, enabling you to prepare yourself for them.

Create a new world around you.

You may be an active Facebook and Twitter guy or gal, conversing professionally on the most important memes of the day, sharing political news with your like-minded friends, discussing House of Cards on Twitter… But that’s all bullshit and you know it. None of that is important, certainly not more important than building your new business, so cut it out!

Get all your social networks, RSS readers and news aggregaters geared towards your new business!

Drop any pointless celebrity gossip updates, any comics or funny videos, even world news! You don’t need to watch YouTub videos about unrest in the middle east right now, you can’t avoid picking up headlines every now and then, anyway. Unsubscribe from all of these things right now — both literally and mentally!

Instead fill your subscriptions and reading lists with blogs, people and sites that are relevant to your new business, as well as to startup culture itself!

Don’t be an addict, be ruthless! Once you have more time again you can always re-subscribe to some of the idle entertainment for relaxation purposes, but for the next few weeks and months you need to surround yourself with the world you’re trying to be a part of!
I cannot stress enough how important and helpful this is!
Creating this conducive environment around you will do wonders both for maintaining your level of motivation AND for tackling that learning curve you've been worrying about.

Organize your thoughts.

If you’re not already using tools and systems to manage tasks and information relating to your project effectively, start now! Ideally, use as few separate systems as possible. All-in-one solutions are best, such as Evernote, OneNote, Google’s online apps - you get the idea. If it’s a development project, look for tools that can hold both administrative tasks and development-specific activities, such as an issue tracking application. I have been able to leverage my day job’s Jira software for my own project, because… well I’m an admin on it, ehem. But be careful, as using company resources could be worse than using company time if it’s not authorized. If you have a supportive and flexible boss or application owner… just ask them.

You need to manage tasks and activities on the building of your product, as well as administrative activities around it, such as budgeting and strategy planning. Then you’ll want to keep track of efforts on marketing, market and other research, as well as general notes and ideas… so if you can manage all of that in a single formalized system or can make few different systems work well with each other, you’re in pretty good shape on that front. And your 6-months-from-now self will thank you for it.

Final thought:

Just start!

Whatever you’re planning, whatever work you feel is needed to get the ball rolling, start doing something. Even if it’s just posting a poll on some related forum as your first piece of research, during your lunch break at work. Or draw up a mock-up of the product or process you envision, write a blog post or save just a few bullet points in Evernote… Don’t fall into the trap of never-ready. Fear of not being prepared for the daunting task of starting a business can make you hesitant to do any work at all at the beginning, and just taking those first few steps is the hardest part. They don’t cost you anything, you can throw in a few minutes of research whenever you browse the internet, you can scribble on a post-it note here and there, you can write a few emails to other entrepreneurs whom you’d like advice from…

Remember: Progress is cheap at the beginning! By the time you need to invest anything like real money or a significant time commitment, you will already be an entrepreneur at heart.