Growing Pains – A Startup’s First Steps

So much has been written about working for yourself and the pros and cons of entrepreneurship, from serious articles to humorous ones. It hasn’t even been a year yet that I set out on doing my own thing but I’ve learned a great deal in this time and I continue to discover more every day. Most of my friends are in startup mode as well, and a few coffee meetings every now and then reminded me that we are in our phase of learning about things most people will never even get to experience.

Quite a few people have asked me what it’s like and what I’ve learned, so I’ve put together a few of the bigger things I’ve learned over this time:


You’ll be called crazy or brave at least a few times along the way. Probably both.

Between friends, family and random strangers I strike up conversations with, I often find myself being told I’m insane for working so hard and I need to ease up, or that I’m brave for doing what they are sure they will never have the guts to do. I suppose you need a spark of madness, or at least mad determination to succeed at getting a business off the ground or working for yourself. You have to be prepared to go far beyond the point where most people would get fed up, scared or unsure, and be too stubborn to just let it go. The rewards are tremendous – on many levels – but I have come to realize having the ‘stuff’ needed to do something like this, is either ingrained in your character or it isn’t…and there is no flaw or lesser strength in either having it or not. It’s as straight forward as being a morning person or not, loving sweets or preferring savoury snacks. In the end, it’s a yes/no variable which you sometimes don’t truly know your placement in, although making the choice to go alone and actually seeing it through already tells you a lot about which side of the fence you tend to be on.

You’ll be disillusioned quite rudely at times and learn all about counting chickens before they hatch.

At first, the help and support of mentors and angel investors seem like the best possible thing for you. While these are undeniably great benefits to have on your journey, you need to evaluate if their vision and assistance is truly in line with what you aim to achieve or if it will stunt your growth – not every offer or opportunity should be accepted and you’re often better off buying your time and securing your footing first. You’ll run into people who offer their help yet end up getting carried away with their own interpretation of what you should be doing, or promise to help yet ultimately never do. As is the case with most things in life, relying too heavily on the help of others means you become dependent, which can seriously hamper your growth and set you up for unexpected falls.

You’ll have to re-think and re-envision everything you initially saw yourself doing as a business.

Initially you start off with an idea of where you want to go and what you want to do, but as you interact with clients and peers, you will be asked to do things outside of the scope you initially envisioned. You’ll also either realize you’re doing something everyone else does and start specializing when you recognize a niche in the market that needs to be filled, or you’ll come into your own and start to identify what makes you different and where your strengths lie. As I’ve mentioned, I have several friends who also run digital startups or work for themselves, yet none of us are in direct competition with each other because we each have strong, individual skill sets that make us good at a particular style of service or working with a specific type of client. Ultimately you will need to decide where you draw lines in terms of your services, or prepare to expand far beyond what you envisioned at first.

Everything is a case of extremism.

If you like balance and predictability, you’ll have a rough time adapting to running a startup. Everything, from workload to income, can completely flip on its head at a moment’s notice. One week you pull 18 hour work days and pray for sleep, the next things become almost suspiciously quiet and just as you become accustomed to a less mad pace, the next wave of mayhem hits. Financially, unless you’ve got retainers in place, you can go from having a pretty great month where all the bills get paid and you get to save a bit of cash in the bank, to realizing it’s the 20th of the month and you’re not sure if you’re going to make rent unless you pull a rabbit out of a hat. It’s both nerve wracking and exhilarating at the same time. One thing you can be sure of is that change is the only constant and that you’ll be on the edge of your seat pretty often.

Extremism also exists in your behaviour, depending on your mindset.

You either procrastinate heavily after a rough, long work phase, or you are overworking yourself to the point of burnout. Moderation is for the meek and this isn’t an apathetic person’s playground. While you’re trying to find your feet and figure out when and how you work best, you’ll probably go well overboard pretty often and be left wondering what normal is again.

You learn a great deal more about yourself, both good and not so good.

Every bit of your personality, character and ethics – both inside of work life and outside of it – gets tested to the very limit when you set out on your own. You don’t truly understand the scope of your limits and abilities while you’re working an 8-5 job, because you’re still in a relatively safe environment where you get to clock out and decide how you spend your free time. The moment you leave that and have to fend for yourself, all of these aspects become a lot more accentuated. If you procrastinated while employed, you’ll find yourself having to fight hard not to put off tasks to the last minute now that you decide your own hours. If you had a tendency to take work home with you, you will find yourself frequently haunted by thoughts about outstanding tasks and mentally extending to-do lists at 2AM while you’re trying to fall asleep. More than ever, you’ll learn that setting schedules and allocating time to every part of your life becomes crucial, because there’s nobody else there to force you to abide to time slots and you can easily get caught up in doing too much, or too little, of something for months at a time. Without fail, you will also become more responsible, more accountable and more meticulous about how you take on your life, and it will spill over into every other part of it as well. You go from being perfectly happy with someone else managing your tax payments and deciding your schedule, to carefully reading the fine print of every document and making very sure you know the ins and outs of everything you are involved in or sign up for. In essence, you take charge of your own fate in a way you never have before.

Sometimes, for a brief few seconds, you envy employed people.

Granted, you will shake off any of that envy within moments of having it cross your mind, but sometimes you’ll look at fulltime employed people and think that they’ve at least got the knowledge that they have a set income and know exactly what to expect at month end, as well as having mostly predictable work expectations. Then you’ll remember how absolutely terrible it is to be forced to work at set hours in an environment that probably isn’t good for your creative or intellectual wellbeing, for a manager who is, quite likely, a dictator in their own right, and that no matter how much extra effort you put in, you won’t reap extra reward if you happen to put in 60 hours of overtime one month. Then you’ll take a break and go have coffee at the mall at 3PM, surrounded by housewives and retirees, because you can.

You may not need to put in sick leave, but sick days cost you so much more.

While it’s not necessary to write a text message or call in with a husky voice to explain that you really feel like a bus hit you and still have to go get a doctor’s note to validate this, every hour you’re sitting in bed staring at the wall with glazed-over eyes, you’re losing money. There’s no company to pay you for sick leave days regardless of whether you reply to mails or sleep the day away, which means flu season can be a real hazard. Also, that bittersweet indulgence of knowing you can crawl back into bed while your co-workers start their day, is replaced by calculations of how many extra hours you’ll have to put in to make up for the need to hug your pillow for a few days.

The space between what you realize you know and what you don’t know yet, will get bigger.

Transitioning into a startup and taking on the world by yourself means you probably already know a bit more than most of your peers, whether it’s because of an unquenchable curiosity that keeps you learning, or the need to advance for professional reasons. As you grow your startup and start interacting on a new level with new individuals, you’ll come to realize there are some extremely inspiring people in a league you just haven’t reached yet, in spite of your experience beyond employment level. For a curious mind, realizing how much more is out there and that you’re in the middle of a huge upward shift in growth, is pretty much the equivalent of letting a kid loose in a candy store.

You realize that client relationships are ultimately interpersonal relationships, and sometimes they just don’t work.

It’s impossible to differentiate your work style from your personality, at some point in time they do converge and it tends to be in the moment you meet a prospective client and as you start working on a project for them. While many times you may not have the luxury of turning down income, you may find yourself at a crossroads from time to time, realizing that your client’s demands and the way they deal with you and vice versa, clash beyond the point of agreeability. At the end of the day, as is the case with everything, it comes down to people dealing with people, and sometimes you just don’t ‘gel’ or play well together and you realize it’s best to cut your losses and move on. In the same breath, finding a client who is completely on par with you and treats you with respect and professionalism, makes for a fantastic, lasting work relationship that very little can compare with. Treasure them like solid gold bars and treat them with gratitude for helping to secure your freedom from an office cubicle.

Wishing for island getaways vs having full throttle drive happens pretty much simultaneously.

You’re fantasizing about a holiday on a remote island somewhere, with minimal use of your phone, except to update your Instagram account with a sunset picture or a shot of your most recently ordered cocktail. Yet at the same time you’re feeling so excited about the next step, the progression of what you’re doing, that you don’t want to stop. It’s a constant mix of ‘I would kill for rest and peace’ and ‘This is amazing, I’m so close to another milestone’. Again, always an elevated state, never a dull moment.


Having said all of this, I wouldn’t trade it for anything else. Judging by the past few months, next year is going to be even more challenging and rewarding, and I wouldn’t have it any other way. Forget taking the bull by the horns…be the bull!


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