Starting a job in a startup

Stefano Bellucci Sessa
7 min readNov 23, 2021

This is an edited transcript of Episode 010 of Design, In Confidence, mindfulness & design podcast with Stefano Bellucci Sessa’s learnings on creative confidence, emotional intelligence, and mental health.

The design decision of hiring you

Before you started working, the startup made a few design decisions:

  • looking for your role
  • hiring you.

In a previous episode, I explained how everything is designed, but not everything is mindfully designed.
So ask yourself:

how mindfully designed was the decision of hiring me?

Keep reading, to find out why you might not be good enough but, most of all, why you might be even more than good enough.

Learn how hiring you is not good enough

The startup probably tried a few solutions in the past.
Some of them were not good, others were good enough with the resources available.

Maybe someone else was doing the task that you’ve been asked to do.
When I joined a startup as the first UX designer, I found out my tasks were distributed between product manager, developers, and design contractors.
Until someone in the startup (informally, or formally, consciously or unconsciously) thought:

[this event] made us realize that we need someone that can [do these things] so that we can [achieve this outcome].

Make sure you understand that event and, even more, its expected outcome. The findings will help you to clarify the startup’s needs and expectations.

Discover what’s expected to happen in the future

The decision of hiring is a solution to address a problem or opportunity that might be:

  • a good enough solution
  • the wrong solution
  • or not enough

Maybe they came up with the wrong solution (and the expectations).
And it’s ok, but you have to get it right by either:

  • meeting expectations by owning what you are good enough for, or
  • setting expectations by accepting what you are not good enough for

As always, unleash your creativity and consider multiple solutions by looking at the situation not in a binary way, but as a spectrum.
For example, “not being enough” will mean:

  • solving problems, but lowering expectations
    (e.g. in a longer time, with lower impact, with different resources)
  • not solving problems, but contributing on finding the solutions
    (e.g. understanding better the problem, hiring a contractor or a new employee)

Align and manage the expectations of your boss and your team.
They might be unrealistic on not what’s best. And that’s okay. It’s normal.
It’s not about you, your ability or hiring the wrong person.
It’s about how your role was designed.
They didn’t have the time, the knowledge, the expertise to define in detail what your job is going to be. You do.

Design your role

It’s part of why you are there – they aren’t subject matter experts, you are.
It’s your responsibility to define expectations around your role.

Investigate the past of the startup but also its future by understanding business goals in the short and medium term for the startup as a whole and for your role.

Everything moves fast and changes quickly in a startup — accept and prepare for your role to soon change too. Understand how.

You should grow as quickly as your role grows.
Keep in mind I said “should”, not “must”.

Startups scale fast and it’s okay if that’s too quick for you, don’t feel bad about it. Especially if you don’t have a senior subject matter expert in the startup helping you grow as quickly as the startup does.

But you “must” accept that (sooner or later), the startup will need your role to be bigger had they will either:

  • promote you because you demonstrated that you’ve outgrown your role
  • accept that you didn’t, and hire somebody else to manage you

In confidence, the latter happened to me.
It was hard to see I wasn’t “good enough”, but I finally had a manager in my same industry, look at the at work, and take note of:

  • a few things I wasn’t doing, even needed or expected
  • a few things I was doing, but not demonstrating to the leadership team – unaware of how much I had outgrown my role

I honestly soon left, also for other reasons.
But try to make the best out of that opportunity to define your areas of improvement.

To recap on not being good enough:

Design your role by understanding why you’re needed and by using it to build trusted relationships with your team aligning their expectation. At some point, they will evaluate (and then, re-evaluate) whether creating that role and hiring you are the right design decision.

But also, by let’s find out why you are already good enough.
Or a bit more.

Why you are good enough, or a bit more

Accept that, for the startup, you are just good enough.
Embrace it.

The startup hired you because doesn’t have the resources or the confidence to invest in a bigger name, team, or department.

Your role is a “good enough” early iteration of that, “good enough” to address some problems and opportunities.

Learning ̶b̶y̶ while doing

In confidence, I always felt the startup I worked for deserved better.
As soon I started to discover all the user’s problems, I felt it even more because I wasn’t enough to address all of them.

Awareness of why you are not good enough might crash you. So accept, prioritise and focus on what you are good enough to deliver and bring value to.

That’s what I did, getting better at delivering that value quicker with time.
This freed up time for what I wasn’t good enough for, so I could learn a lot about design leadership, practice skills and tasks I wasn’t confident in, and understand how to delegate some of them to future hired dedicated experts.

Learn like everyone else

It’s okay to be good enough in a startup (and in life).
Trust me: everyone is only good enough.

They might look confident, like Morpheus or Trinity in the Matrix, only because:

  • they are unaware they aren’t good enough
  • they are aware, but pretend not to
  • they are aware, but own it

I suggest to go for the latter.
It’s impossible to have everything figured out and achievable, because every startup has many unknowns and tasks to address with limited expertise and resources.

Increasing your experience means increasing your awareness of all the problems and opportunities that you should address, but you aren’t enough for.

Experts’ creative confidence comes from being mindfully aware and in control of limited resources and potential, and make the best out of them.

Mindful design brings it to accept that you’re on a journey.
In the future you will get better, but focusing on the here&now will show you why you’re already good enough, and why you can do even more.

Yes, you might be below the startup’s expectations for a few reasons and unable to meet (yet) a few others.
But you are already able to go beyond the start-up expectations.

Learn by stretching your role

Everyone is stretching their role by being outside of that comfort zone. Their failure or modest impact is (or should be) accepted from everyone, because they are learning things about their job, the startup, and sector as they go.

Take the initiative to learn, try and impact beyond your job description, owning tasks without a dedicated expert (or that you are better enough expert than others).

Stretch beyond your role and you salary, looking for opportunities to capitalise that experience because:

But remember to be mindfully aware when your salary/effort/expected impact (a.k.a the startup’s “return of investment”) aren’t good enough for you. Show the startup when investment in a pay rise or a new team member is needed.

So, to wrap up…

Temet Nosce

The sign in the Oracle’s kitchen in the Matrix.
As she tells Neo:

It means “Know thy self”.

I wanna tell you a little secret:
being the one is just like being in love.

No one needs to tell you you are in love.
You just know it.

And that’s I suggest you to do.
Know yourself by:

  • Mindfully discovering your role
    Find out why you’re needed so that, you know (and let them know) why you are the one meeting their realistic expectations.
  • Mindfully designing your role
    Define and stretch your role (and let them know) beyond their expectations.

And let me know how it goes.
Let me know how you find the confidence to start working as a startup.

Or let me know if this blog gave you some confidence.
Clap, share, comment.

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What I share doesn’t represent any of my current or former employees.
But I thank
EasyPeasy and Fluxx, for giving me these amazing learning opportunities.

Please review, and share it with others.
Tell people why you found this valuable, and that you are a safe space to find support in building their creative confidence.
If you got this far, I’m sure you’re a great listener — which I thank you for.

And now, it’s time to listen to your thoughts.
And remember to thank yourself, for the time you spent to learn, and grow.



Stefano Bellucci Sessa

Innovation consultant and design thinking evangelist, helping organisations create experiences that improve the world we live in.