Corporate to Creative in 10 Gruelling Steps: A Realist’s Guide

You are sitting in a grey  office on a gloomy day, tried, and after yet another frustrating day, you are thinking your life is going to waste.

You take your phone, and see a person – maybe even a friend – sipping cocktails on a tropical beach and bragging about their freedom, and – more gratingly –  being bale to afford a care-free, happy life by posting photos of cats, or cute flat-white pictures.

You sigh.

After wondering what went wrong in your life (“But I worked so hard! And went to good schools!”), an idea pops into your head. Maybe you too can embark on this journey to fulfilment, wealth and/or fame by showing your creative side on social media.

“Why don’t I film myself reciting shitty poetry? Or write restaurant reviews? Or have a podcast with my two friends about contemporary culture?”

You google around, and you see swathes and swathes of pages urging you to follow your passion, thousands of videos telling you can make money by following your dreams, and maybe even a few helpful courses that will – for a small fee – make your creative endeavour a cash cow.

This gives you a skip in your step and you think that maybe the first creative endeavour you will undertake, is a resignation letter. 

 From the on it will be beach, sun and fun, fulfilling, meaningful work and you will finally show to the world that you are not just another corporate cogwheel churning money to your clients/bosses, but a creative, multifaceted, talented individual. The world will celebrate your true self and you will bathe in cash, and rather than hunching over Excel or aligning crappy boxes in PowerPoint all you will only need to take nice photos and write witty, heart-felt articles…  


  1. Don’t do it for the money


If you like me found a relatively well-paid corporate job straight after uni, you probably never experienced how difficult it is for people to part with their money for anything you do. Although the choice of what you do will have a big effect on this – people will pay more for excellent food you cook, rather than funny videos – money, especially in the short term should not be the primary driver. Although, admittedly, it should also not be an impediment to pursuing your new plans, never forget creative (and entrepreneurial) world are synonymous with financial stability – there’s a reason why writers, actors and musicians were more associated with poverty than investment bankers, management consultants and lawyers.

  1. Don’t do it for fulfilment or happiness

Although work is increasingly seen as the main avenue to seek fulfilment (especially for under 30s) and happiness, changing careers, even to something you deeply enjoy, may not, in the long run, really change all that much. Of course, if you hate your job, day-in-day-out, quitting will definitely make you happier, and, similarly, doing something different will give you a much needed rush of joy. Nevertheless, even if you feel you are spending your productive energies more meaningfully, you can still find yourself feel stuck in other areas of your life. Given how much of our identity is bound with our careers, you can also feel like you lost an important part of who you are, or you may miss other aspects of corporate life: socialising with colleagues, predictability and a certain standard of living it afforded you.  If you are feeling deeply unhappy and dissatisfied, you should try to delicately address your wider life – maybe with help of a therapist – and avoid making rash, dramatic decisions.

  1. Don’t expect it to be easy


While you may indeed enjoy taking hot photos of yourself on the beach or baking amazing vegan cakes in your spare time, turning that into a paying career is difficult and often gruelling task – I mean, if it was really easy, everybody would do it? For most people the toughest aspect is the one related to promotion and sale, especially in a field they may not be fully familiar with. It is a delicate and very useful art to know how be heard in the world where everybody is shouting, without feeling like you are betraying your integrity and privacy. It is a delicate balancing act which may take a lifetime to master even for those who have proven themselves very capable in the lower and middle rungs of corporate environments. Secondly, perfecting own “art”, even if you enjoy doing it, is arduous and takes a lot of thinking and practice, which may also make you feel exasperated. As Mark Manson eloquently put it, you should only do something if you can handle (or better, enjoy) the shitty aspects of it.

To make it more concrete: liking beautiful photos is not enough to “boss” Instagram. You also need to be able to endure (or like) the following: making 1000s of crap photos (occasionally in shitty weather), spending time pouring over occasionally stupefying photo editing software, maintaining your equipment, learning how to look the way you want to, endlessly trying to figure out what “works” by seeing likes, and only then “hustling” to see if you can make at least some money for all that effort.


  1. Don’t expect widespread support, even from those closest to you

“Don’t expect me to believe in what you decided to do”

Those were my Dad’s words on the first night I embarked on my career in writing/media. Two years in, we still regularly erupt into pleasant discussions on what I exactly expect from the future. Many of my friends do not give a toss about my creative projects, others only have very chilly reactions. Others yet often feel compelled to add that “he had a real career before in London”, when I say that I write for living. Although you will not like it: that’s life and don’t expect it to be otherwise, especially if up until now you lived surrounded by corporate-types who naturally value corporate lifestyle more than what you may be embarking on. If you live in environments which greatly value titles, steady jobs and financial success, prepare for daily challenges. This will especially hurt if you were used to praise for having done “right things” at school and at work up until you decided to do things differently.

  1. Plan the best you can


While creative life is considerably more unpredictable than climbing the relatively pre-set corporate ladder and receiving monthly pay-checks, it does offer options to plan and manage you risks. Firstly, try to get a realistic ideas of the workings of the new field you are entering, ideally by talking to (realistic) insiders. What is the business model? How much money can you expect at each stage? Who are the “gate keepers” to success?  What are the main trends and who/what sets them? What resources are there? Who are the top dogs? What are the main countries/cities/neighbourhoods where you can sell your wares? These things greatly vary depending on the industry: from managing Facebook algorithms for bloggers, to charming gallerists for visual artists. From there, to understand what niche you can/want to occupy and how much potential is there. Then, try to see how you can use resources and skills from your corporate days to differentiate yourself. Use all of this to make a rough sketch of what you can expect in the short and medium term, and set own metrics for success (i.e. page views, earnings, meals cooked, yoga classes held).


  1. Do it “like a motherfucker”, but prioritise to avoid burnout


The difference between the people who are truly successful writers/painters/chefs/… and those who are in it for the “cool” and the lifestyle, is that the first category put their full body and soul into what they are doing. Although it is tempting to use these careers as a placeholder when someone asks you what you are doing, while you are actually just taking a break from a corporate life, if you are serious about doing them you need to work and think hard about them every day – basically doing them “like a motherfucker”, as Cheryl Strayed would say. This means that you will be working at least 9-to-5 type hours (although maybe more flexibly) and carefully honing your new skills (either in your core work or in sales/marketing). Furthermore, if you love what you are doing and/or want to make it, you will probably want to do much more than you can realistically (or physically) manage. If you are a bit of an A-type obsessive, this can lead to a burnout and make you really miserable doing what you love (see under 2.). The difference between those who hate their “callings” and eventually let them ruin their life, and those who manage to pursue them more or less happily, if learning how to prioritise. This is especially important in the beginning when you are trying to find your niche and deciding what to learn and do first, as you can be overwhelmed by the possible paths to take. Whenever you are feeling frazzled, I suggest making a three-dimensional matrix according to what you enjoy doing the most, what elicits the best feedback and what pays the most.


  1. Expand your environment


Obviously, in order to be able to keep abreast of the developments in your new field and the opportunities there are for you, you should make a few friends in the field, and use main publications/blogs/websites/podcasts. However, you will also need to do this to be able to share your new experiences, worries and fears, as there is a high chance that your current environment would not fully understand them, as they had little exposure to people in creative careers. What makes it worse is that some corporate professions foster fault-finding or relatively narrow mindsets (it’s all about sales!), which can be a challenge if you just emerged from them.

Although there is a high chance you will bump into a lot of pretentious, unhelpful fellow creatives, majority of the people like anywhere are nice and want to be helpful and share their thoughts. You needn’t necessarily limit yourself to people in your new field, but people with similar experiences and lifestyles who you can have a coffee and a moan with at 10am with while your corporate friends are busy. If you are not a natural in making friends at bars and evets you can organise groups, drinks or arrange interviews. Besides this, as a writer/podcaster I found the following podcasts very useful:



Tim Ferris Show


  1. Be careful with taking advice


Although creative careers are difficult to succeed in, they are (unfortunately) easy to have opinions on. Your corporate friends and colleagues are sure to shower you with a lot of advice of “why don’t you do it this way” especially, in the beginning. Some of these nuggets will be invaluable and allow you to see things differently, learn and improve. Majority, however, will only make you confused or waste your time. Best advice will be the one you ask for, ideally from the people whose opinions you respect, and with a clear idea of what you will use it for. The more you ask for specific, “actionable” advice the less you will feel the compulsion to listen to unsolicited random ideas of non-experts.

However, one question you should never ask anybody who is not your closest, truest imaginable friend, is whether they think you should do what you are doing – that you should know.


  1. Be patient and open


Unlike school or graduate career path, with annual performance appraisals and promotions, creative careers tend to meander and spurt. Frustratingly, what you think is your best work may be completely ignored, while your lesser works succeed. You need to give yourself time to find your feet, and that means not a couple of months, but probably at least a couple of years. Yes, it is frustrating for a lot of A-types, but that’s the only way.

The best thing about a creative career is that you can often make pivots and yet still transfer the basic skills you learned at the beginning: once you learn how to not be ashamed of your expression and viewpoint, you will be able to know how to express yourself in poetry, writing or photography (albeit with different levels of technical skill). Similarly, if you learn the golden art of selling your perspective on the world, you can use it for anything. This means that you can afford to be open to new possibilities and follow your gut, a bit more than in the regimented life of a corporate.


  1. Just do it


If you feel the urged to be creative and see if you can make a living out of it, you should definitely do it. Should you leave your job and risk starvation for it? Probably not. Nevertheless, you should try to do it in some shape or form: on the side, even if you can only spare an hour a week. Sharing something you enjoy doing with the world is an extremely liberating and life-affirming feeling, even if it does not make you money. I never regretted my choice, and I don’t think I ever will.  Even if might have to climb the hamster wheel again in the future, writing and podcasting not only felt great to do, they also opened my eyes to how rich the world is, and equally importantly, to how much more I can do outside the office.

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