Your guide to Leaving Corporate, and Becoming an Entrepreneur

So you have a burning desire to become an entrepreneur and run your own show, but not to give up the comforts of slavery, right? That cushy salary, being told what to do every minute of your day, all the comforts of your cubicle or open plan office, politics that makes Survivor look like a kindergarten picnic…?

Leaving corporate isn’t easy, I was trapped there for 20 years before being pushed out the nest by a company where I was hanging on by my fingernails, having long passed by sell-by date.

Six years later I am rocking and rolling, thanking God every minute for that fateful day when they told me I was retrenched. I put on my saddest, most disappointed face when being given the news, and afterwards, in my car, I literally wept with joy and relief.

There’s nothing worse than being wrong for a job.

There’s nothing better than losing that job.

There’s nothing better than starting your own thing.

There’s nothing harder than starting your own thing.

Let me talk you through a few things I’ve learned along the way and a few strategies I have for leaving corporate.

1. There’s no Short Cut to Finding your Purpose

Everyone is banging on about your WHY, your purpose, passion and destiny.
I have 19 year olds asking me when they’ll find their WHY. I have 50 year olds asking me the same.

My opinion is that your twenties and even your thirties and forties are for learning. And then suddenly a point comes where everything clicks and suddenly you’re living your purpose, you’ve found your why, and you’re doing what fulfils you, what you were born to do.

This might not be true for everyone, but in my experience, I had to learn a lot about things – life skills, work skills, people skills, me skills…and when I started my own company everything I’d learned came together in this holy synergy.

All paths merged into a single destiny. Personality, passions, knowledge, experience all melted together into my purpose.

There was no shortcut for me.

What I’m trying to say is, don’t leave corporate before you’ve paid your dues, and learned your lessons. There will come a time when you’re given a tiny, infintessimal window, a window you will need to leap through from a fast moving train and you only have a few seconds to make that decision, if you miss that window, I can’t promise another one will present itself quickly.

You will know when that window is there. Take it.

2. Soft Landing: Starting at the Top

So you leapt out the train and made it through the window, well done! That is some Trinity from the Matrix level stuff there.
If you landed softly, that means that you left your corporate hell with one or two clients en tow. You sneaky dog, you! That’s fantastic! That means that you’ve left at the top of your game, and started your own thing at the top, and you’ll only go upwards from there.

I have a few clients who did that, exited an industry where they knew everyone, were well connected, had a few clients join then shortly after going on their own, and they continue to charge top dollar for their services.

Good for them.

I strongly suggest you follow suite. Network with all the big dogs, make sure they know who you are, trust you and would work with you if they aren’t already. Get one or two of them to commit to sticking with you and anchors aweigh!

3.Hard Landing: Starting at the Bottom

This is where I landed after being thrown from the train…even though I’d worked at a Cape Town-based company for 6 years, I hadn’t met one person in Cape Town, because all our work was done in global markets.

When I started Shift ONE I had to start from the bottom. I also had never run an advertising and digital marketing agency before. I had to find customers, figure out how to apply my knowledge to help them grow, and then find more customers, build a team, and then find more customers.

I have often wondered whether I could have done it differently. But no, I keep going back to the fact that I knew nobody locally, had no local network and had no committed clients.

I got involved with the local startup community at the Bandwidth Barn, attended a few courses, got desk space at their co-working space, got my first clients, my first staff members and built up my business to where it is now…14 full time staff members, expanding to Sandton and the UK, launched a Digital Marketing Academy, and working myself out of the day-to-day operations of both businesses.

This approach isn’t ideal, but it’s necessary for some, as it was for me. Get networking as soon as you can and make sure you have at least a 6 month runway (money in the bank) to help you survive until your first clients turn up.

4.In Parallel

This is the approach I’ve advised a few of my senior clients to take. Start something on the side, a consulting gig or work evenings and weekends on whatever your passion project is.

This way you can see whether it’s something you really want to do, without quitting you day job.

You also see whether people want to buy whatever it is you’re selling.

It can, however, be exhausting.

And you have to make sure that your company doesn’t have policies about moonlighting.

It’s going to be tough, there are going to be many days when you yearn to go back into slavery, the big salary will call you, the comfort of working so many hours overtime with no reward, the security of your position there (not)…you just have to remember that hard times pass, that you are going to learn a lot, pass your tests, face your giants and get stronger.

It’s worth it.


If you want to know more about ways to leave corporate and go it alone, please subscribe to my new YouTube channel and watch the #AskDK show. You can post your questions to me using the hashtag #AskDK via any social media channel, and I’ll be sure to address your questions on the show.


Dylan Kohlstädt is the founder and CEO of Shift ONE, a creative integrated marketing agency, and the recently launched Digital Marketing Academy. She has also recently launched her YouTube #AskDK channel, targetting entrepreneurs as well as digital marketers.

Dylan is an online marketing specialist who is passionate about helping entrepreneurs and start ups succeed.

Dylan has 20 years marketing management experience in insurance, financial and property industries, and in online marketing involving web, mobile, SEO, CRM and Social Marketing and is considered a subject matter expert on all things digital.

She has extensive local and international experience (South Africa, UK and Australia), has managed global and national brands and is experienced in managing multiple product ranges in multiple languages and countries.

Dylan also has an MBA through UNISA SBL.

You can reach Dylan at:

Shift One

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