SUPER-BLUNT FAQs for Quitting Corporate Life to join a Startup

(FAQs down the back if you don’t need to primer)

Introduction

If I could describe the one key and overwhelming difference from moving from being a lawyer, banker or a consultant to working in a fast growing company (or starting your own business) is the transition from being in the world of people who talk about doing, to the terrifying world of people who do (and often fail).

This is not criticism or exaltation of either and definitely not an exploration in the benefits of the former over the latter. Enough surface level articles would give you the framework for thinking through whether the transition is right for you “it depends, your lifestyle preference, your risk profile, your stage in life, your mortgage or your current or prospective family commitments, your working style, your dream goal, your hobbies” the list can and definitely does, go on.

Rather this is my experience of a very particular transition - both of the concerns expressed to me by people who want to change, and the experience of seeing people who have done so.

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The source of value

The starting point for thinking about the implications of a transition and the “where can I fit in to this?” is with an unpopular opinion.

All advisory is glorified sales.

The advisory business model is predicated on the ability of the Managing Director or Partner’s ability to sell the teams specialised skillset This is why you will see managing partners who may not have shot the lights out as juniors, begin to thrive when doing the work becomes less important than selling the work. Doing the work is what hardworking juniors (you) are for.

Because they are closer to the creation of value for the business they are in, they command the highest remuneration, and this is why they also have a nicer car, watch or house than you, but maybe a worse marriage.

The implication here, is that upon moving to a business where selling ideas, advice or process are no longer the key drivers of creating value, it is likely that without upskilling you will need to take a discount on the value of your opinion — unless you’re a founder, you’re probably going to land further away from where value is being created.

What does this mean

While you may have covered the industry from the outside, done your research and been very well read, the gap between how good you think you may be at solving problems, being ‘strategic’ and the realistic value that you can provide at an early stage start up who needs do-ers is probably pretty wide without a willingness to roll up your sleeves and literally just do stuff.

I’ll give you a personal example — When I was at a bikeshare company working in a warehouse with a group of contracted Nepalese removalists we moved bikes morning and night into an abandoned very dark and very terrifying abattoir. The people who were most valuable were the people who would show up and get things done, not the people who could hypothesise on how to 1% improve my process. This is the same way I approached the task of moving 10,000 40kg bikes. You need it done, so just do it.

…This implies that, in order to be super valuable you should be willing to do whatever it takes* to get the task done.

Your ideas are worth something, but stand alone not more than the next person’s who can just do the thing..

FAQs

When is The Right Time to Leave?

The right time to leave, is predominantly a question of a honest appraisal of your own ability. For some really great people that I’ve worked with, they probably didn’t need the corporate training that graduate programs typically provide.

That definitely was not me.

I consider myself a slow learner, and definitely benefited from surrounding myself with smart, structured people for a few years, until I half figured out what the hell was going on.

But the ‘general learning’ starts to plateau, and that is probably around 2 or 3 years. This is not to say that you are not learning at all, but rather that you are learning things that are hyper-specialised to your industry, sector or coverage area. It is also more likely the time when you commence managing people (even more-junior juniors, or grads).

When making the choice between ‘managing juniors’ vs. hands on experience in industry (in a startup or in a small business or running your own thing) it is likely as a junior that hands-on experience will trump ‘managing others’ every time. Employers will generally assume, if you’re well spoken and seem like you can get things done, you can probably figure out how to manage other people (and if you don’t now, you can learn).

The right time to leave, is when your next year looks like it will feel a lot like the last year

But isn’t it risky?

But isn’t it risky, to do your own thing, start your own company or join a rollercoaster startup that will probably end up going the way of Xinja, Wework or even ENRON ??

Yes, it is. But allowing yourself to be at the mercy of capital markets, partners being poached, businesses being disbanded or getting too senior or encumbered to leave, is also risky.

While it is true that the path is less structured. Assuming that you worked hard enough at wherever you are now, the corporate/advisory world appears to have an almost insatiable for people who are getting things done (the bias here is that we’re in the central bank forever-bull-run so this statement is definitely product of its time).

This means, if things blow up in startup land, the worse case scenario is you end up back in the job you’re in now, with a story, lateral real world experience, a wider network (who maybe you can sell your services to down the track) and a group of colleagues who are probably jealous that you had a crack.

The risk after leaving, appears much smaller after you have, than before you do

What is the right role for me?

It is likely that without a previous experience in areas of the business where value is created in actual products or things (creative, design, marketing, engineering) that you will end up in operations. This is generally the land of practical-smart-generalists, who do things.

Operations is usually the most likely exit/entry point for corporate escapees.

What is The Hardest Part?

Time allocation.

Working hard vs. work smart vs. working hard and smart.

In most high pace advisory environments 16+ hour days are the norm, when I worked in Singapore the average finish time was 4:00am and in Sydney I regularly worked until 2:00am for many years. That entire time, someone was telling me what we needed, or at least the outline of what we needed to do.

It feels like working hard, and it is taxing, but it’s not hard.

Upon leaving, to join more unstructured environments, it’s super clear that burning the midnight oil to produce more output, doesn’t necessarily lead to better decision making and worse, doesn’t lead to better outcomes.

Nights and weekends you’ll need to crack on, to get things done, but predominantly the difficulty is understanding the change in thought process. Feeling like you need to be constantly working, often trumps the feeling of feeling like you need to be working on the right thing.

In advisory world, the more work you do, the better you look internally as a junior, even if the thing someone asked you to do is absolutely fucking stupid. In a world where only results count, only doing work that creates value matters, and deciding where the highest yield on your time, is the thing it appears most people find difficult to grapple with.

Decision fatigue is real, 80/20 is real, doing what you can to get a directional answer before moving on as legitimate strategy, is 100% real.

It appears to me that the hardest part for people leaving is understanding that the “where” you apply your energy, is the step before and equally as important as “how much” of your energy is applied

• caveat this however you want, within the law, within your morality, within reason

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