The Project Manager And The Creative Entrepreneur
We work with a lot of startup founders who come from corporate jobs, or who have been high achievers in various parts of their life.
They bring a strong CV, valuable skills and a passion for their project.
And yet when you start working alongside them, you begin to sense a tension that disturbs them – two parts of their personality that are pulling against each other.
Interestingly, there is no “hero” or “villain” here, it’s not the little cartoon angel and devil on your shoulder.
Both of them are valuable and both of them need to be heard.
We can’t just “tune one out”, we need to find a workable solution that gets the best out of each of them.
Let’s meet them:
The Creative Entrepreneur
Your inner creative entrepreneur is a big picture thinker and a do-er.
It’s a voice reminiscent of a kid looking out of a car window, imagining scenarios, asking questions, making plans and requests.
It has a sense of adventure, it hates boredom, it stirs you into taking action.
In many cases, it sees a future that benefits a lot of other people, and is inspired to build a valuable, necessary company.
The creative entrepreneur:
Wants and seeks out change
Thrives on uncertainty
Does hard things
Makes promises and makes sales
The Project Manager
Your inner project manager is a details-oriented person and a do-er as well.
It’s a voice reminiscent of a parent driving their kids around on holiday, keeping the trip on the rails, checking that everyone is happy and has been to the bathroom because we’re not stopping for another hour.
It wants to do a good job, it hates chaos, it stirs you into doing what you need to do.
In many cases, it wants to do right by other people, avoiding letting them down, protecting your credibility and relationships.
The project manager:
Wants stability
Wants certainty
Makes things easier for those around them
Delivers on promises and timelines
They’re both great, but they’re not good housemates.
And they clash because they’re both fighting for control of your calendar, your attention and your reputation.
Entrepreneurial vs Corporate Mindsets
Both of these voices have strong arguments, neither of them are wrong, but they can flare up at the wrong times, particularly when fear is involved.
Some parts of entrepreneurship are not compatible with a corporate employee mindset:
Entrepreneurs accept and embrace a level of risk that would be frowned upon or forbidden in a larger company.
Project managers spend more time on managing appearances, especially with supervisors and stakeholders.
Many say they have to fight for recognition within their own team.Since entrepreneurship offers no clear career progression, it’s easy to feel like you’re falling behind on your peer group or where you’re “supposed to be by now”.
Entrepreneurial planning involves sitting with uncertainty, thinking about scenarios and not being afraid to change long-held plans.
Corporate employees are instructed to create work that is totally consistent with everything else the company does, whereas entrepreneurs need/want to experiment with styles, tone and what’s on the menu.
Both types of work involve labour, but entrepreneurship has a different layer of emotional labour that comes from investing so much of yourself into the work.
It carries your name, and failure is sometimes harder to brush off.
As Nassim Taleb put it: “The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”
Moving away from stability is a tough adjustment.
Change is uncomfortable, and not all of the habits that helped your corporate work serve you well in entrepreneurship.
That’s why we need to find some sort of arrangement…
Negotiating With The Two
A 50/50 power split doesn’t tend to work, as it leads to overthinking and paralysis.
What might work is taking shifts, in which each side gets designated time to be helpful: using sprints and a grace period.
In this arrangement, your creative entrepreneur side gets a length of time, say 2-3 months, to make massive progress without judgement and over-analysing.
e.g. to hold 30 customer interviews, to create 20 designs, to post online three times a day, to run a pilot, to spend 100 hours in the studio.
After that sprint, your project manager gets to critique, assess and help plan out the next steps.
That way, they’re assessing something like a Minimum Viable Product, not the first crappy draft.
If the MVP sucks, you’ll look at your options and go in another direction.
This is the same advice we give on writing articles – when you’re getting started, don’t post them on LinkedIn one at a time as you create them.
It’s the wrong audience, the wrong pacing, and it makes it hard to find your preferred writing style.
Instead, we tell people to write batches of 10 articles at a time, editing them as a set so that they feel consistent.
Write without overthinking, then critique them as a set.
Then schedule your posts to go out while you write the next 10.
It might miss some feedback, but it creates the habit of consistently publishing work, which is one of the best habits to train and do on autopilot.
You might think “Well that’s easy to say, but how am I supposed to not think like a project manager in these grace periods?”.
A good option is to still be a project manager, but only looking at the lead measures, not the lag outcomes.
e.g. pushing yourself to write, to call, to build, to pitch, to design, without looking at clicks, revenue or your social media following.
Your project manager is so valuable for saying “Hey did you work on the pilot today?”, poking you about your efforts, not your tangible results.
What To Bring To A Pre-Accelerator?
As a team who run startup programs, we’re usually most keen to work with the creative entrepreneur, although we do appreciate that it was probably the project manager who prepared and lodged the application.
We’re asking you to trust the process – to try things that might feel like you’re taking the long way around, or that have no immediate payoff, or that duplicate work you’ve done in the past.
The point of a pre-accelerator or growth program is to intentionally do creative entrepreneurial work.
It does not come with certainty, it is different from a busy season in a corporate job.
For that reason, we generally ask people to set up a grace period for their work, where they won’t second-guess themselves and feel guilty about indulging their creative entrepreneur.
And we invite them to honestly critique their progress in the middle and at the end of the process too – the main person you need to persuade is yourself.
You need to be persuaded that there is a real market, a real opportunity, a real business model, and real assets that can give you a competitive advantage.
These take time to emerge, but you get final say over whether you have a business opportunity that you genuinely want to pursue.
Specific Terms For Your Negotiations
Project Managers hate vague promises, so let’s end with some very clear recommendations for your own internal dialogue:
Doubt and urgency are helpful at the right times, and they can also undermine your startup if they hang over all of your work like dark clouds.
You never need to pretend to like anything, your inner sceptic is welcome at certain points in the creative process. Suspending judgement is not the same as fake smiles.
Designating a sprint or a grace period may seem overly formal, but if it’s stupid and it works, it isn’t stupid.
You get to set the terms of these periods, but as a guide, 6-12 weeks is a helpful starting point.
Sprints or grace periods are not lax or lawless, there’s a lot of work to be done, but we’re not questioning why we’re trying this in the first place.
It’s helpful to be disciplined on the lead measures – the attempts made, the hours put in, the small acts of courage. Push yourself, don’t give up too soon.
Set rewards for attempts, not outcomes. E.g. rewards for doing 15 customer interviews, rather than for hitting certain levels of positive feedback.
Genuinely celebrate your efforts and your work; miserable people love discounting their wins by focusing on the next horizon.
The point of the work is to do the work. If you’re constantly trying to shortcut the process, ask yourself what’s truly driving this urgency and corner-cutting.
If you’re grappling with this type of arrangement, talk with a coach or advisor. It’s not them versus you, or them versus your project manager, it’s all of you versus the problem.