Myths I believed when joining a remote start-up

Doubts that creeped in as I worked at Advisable.com.

3 metal links connected. The middle one gets broken. Links on the right start to take some life through colors, as the others look faded.

Me joining Advisable was a big surprise. Not because I didn’t want to get hired, but rather because I didn’t think I was ready.

It wasn’t my only insecurity. There were plenty of unknowns and thoughts on whether I could adapt, deliver great work, or fit into the team. Some of these were clearer in the beginning, but others were hidden somewhere in my subconscious, giving me crippling anxiety at times.

A healthy start-up culture and a great team debunked some myths for me pretty early. With the rest, I had to struggle myself and understand where my mind was faulty.

This is an ongoing process that’s far from being over. With some insecurities, I made peace and understood I simply had had the wrong expectations. Others are still a work in progress. It’s a process of finding what works for you, when it works, and how to adapt when things change.

My insecurities will appear in my next efforts as well, but hopefully, I’ll be able to identify them faster.

I thought I would agree with any idea because others were more experienced.

This didn’t exactly bother me. I knew that it would be an immense opportunity, so following instructions from people with more experience didn’t sound bad.

However, I was immediately discouraged from being a yes-man. It wasn’t something said directly, but Peter (Advisable’s CEO) always tried to hone and promote independent thinking in everybody. His questions were framed in such a way you had to judge for yourself.

With time, I understood that if he wanted help with something, it was because I had more time, passion, or curiosity in that direction. He entrusted me with some tasks, then I had to explain my reasoning and why it would work.

Every meeting related to Advisable was a conversation. Nobody in the team was the boss. You might’ve been responsible for one initiative but that didn’t make you a know-it-all. Most projects progressed through conversations and debates, everybody bringing ideas to the table and highlighting possible mistakes.

For most, this was natural. They had left their previous jobs looking for more impactful roles with bigger responsibilities. For me, it was tougher as I didn’t believe I could take on that much accountability with no prior experience.

But confidence, experience and mindset came with time and some guidance. Colleagues praised my work, Peter eased me into taking on more responsibility and provided me with the tools to do so.

I thought that I need all my skills fully developed to get hired in a start-up.

My journey in design and Webflow started in the summer of 2020. The opportunity at Advisable arose in February 2021.

My skills in both these tools were way off the mark — at least, that’s what I believed since I admired people way ahead in their careers and compared my work with theirs.

But here’s the key. Not everyone needs the people I was admiring, not everyone can afford them and not everyone knows they even exist.

You’ll always admire people that are better than you, because just like them, you want to improve your craft. But some companies out there need you for the skills you have now and your ability to evolve.

There’s a phrase that I often hear when scouts/pundits talk about NFL players before the draft: “That kid has a higher ceiling”.

Your skills will come from implementing ideas and repeated practice, not from consuming. Consumption is sometimes good for sparking ideas. Practice will be critical to getting closer to the people you admire. Start being prone to taking action and implementing.

I thought it was either black or white. I’m either ready for the new opportunity or I’m not. And if you’re anything like me, you’ll never believe that your work is good enough. Even more so if you’re just getting started.

I’ll probably always be in that gray area. Thinking that me or my craft are not good enough for the job that I’m dreaming about, but trying to get there. It’s my duty to apply for these jobs and jump on the opportunity if presented. That’s because I want better, more impactful roles or projects. These roles rarely come without making your own luck.

So make sure you show people you have a high ceiling.

I thought I’d have to work more than full-time because a start-up needs your entire energy, focus, and time.

Often times 8 hours of work should be enough. Whether it’s a one-man agency, start-up, or huge corporation, work will never stop.

A start-up needs lots of energy from everyone involved. It requires its people to do more than their job description or title (if they even have one). At times, you will either have to or want to work more than your schedule says.

But this shouldn’t be the norm.

You’ll learn that solving big problems takes months. You’ll see that planning a new product or setting a vision for it can take weeks. And as a young, passionate professional you want to do it now, fast, and perfect.

Hustling sounds fun until you understand burn out. Working 10 to 12-hour days is not the norm. It’s nice if you want to do it, but make sure it’s sustainable and you understand that it’s not required.

Sometimes, downtime can bring more clarity than forcing out a solution through work.

I thought working for a start-up wouldn’t provide job security and I’d stress about unemployment.

Parents and society instill this in you so that you have the security they couldn’t. And by definition, start-ups are not secure.

It took me a long time to appreciate both sides. Job security and some stability in your life are essential. Yet, you might want to or feel like you have to take a different path. Given your circumstances, you can partially trade in one or the other and reach a balance in the end.

Know that there are ways to mitigate your risk.

A frugal lifestyle and saving early was my way of doing things. It provided me with more security and freedom than I ever thought possible at 23. Of course, I wasn’t blinded by the dream of working at a start-up. I did my due diligence asking about the runway, possible bonuses or raises.

By knowing the insecure nature of the company, I saved more cash than probably recommended. It paid off. When Advisable shut down, most of us were shocked. It was almost a complete surprise. But it wasn’t the time to panic as I had a safety net.

Not everyone will be in my position, but you shouldn’t be scared to join a start-up because it might not be “a secure job”. It taught me way more than I could’ve gotten from a more stable and comfortable company.

Knowing that I could take on accountability for a project, manage myself and my time, adapt to different circumstances, provided me more satisfaction and stability than a comfortable corporate job could.

I started to understand that the skills I develop will afford me with the freedom and stability I want. It’s not the job, manager or company.

I thought that design is immediately valued.

No. If someone hires a designer it doesn’t mean that they value the role immediately. They might recognize the need, but there’s still a long way to make design a core part of the business.

The number of teams that have design as a core value is small. The number of teams with a founding designer is even smaller. This profession is not respected by lots of people as they believe nice visuals are an extra. What they don’t get is that design is rarely only about nice visuals.

You need to start selling design. There will be times when you know the right way of thinking about a feature, yet you have to design it differently. It won’t be easy to push forward a design change, to explain why the platform needs your idea, or your way of implementing it.

Now you may say “I’m not a salesman, I was never good at this stuff”.

But it’s necessary. Even if you’re a junior, you’ll need to explain the importance of design. You’ll be required to read, research, and convey it. Not by your boss, but by your calling, or desire to do a great job.

Selling design shouldn’t imply tactics or strategies as in movies. It’s you reasoning from the foundations of design and communicating it as clear as possible to others.

There will be moments when people will follow your ideas. Some of them might even prove successful. You need to take notes on both the ones that hit the nail and those that missed it.

Documentation and/or writing is essential for becoming a great designer. It’s not only that it improves your thinking, but it will also allow you to become a better salesman of design. It will  enhance your ability to push your ideas forward. Through writing, you clarify your process, ideas, and communication abilities.

I thought that working remotely will hinder clear communication.

At times that might be true. Zoom, Google Meet and the rest of video conferencing tools might not be the best. But I believe they are not the main culprit.

People not knowing how to clearly communicate their ideas is the main factor. The medium matters less when your arguments are all over the place.

Without good communication skills, the dialogue is confusing in the offline medium as well. But online, it matters more. You expect the instructions to be clear. You zone out when someone is ranting about a subject without connecting the dots. You want to move fast, get to work, and understand the idea as soon as possible.

For this, you need a certain level of seniority or the practice to become a clearer communicator. It can either come with time, or with your efforts to improve it. Me writing this piece is an exercise to better convey my thoughts and feelings.

Something I struggled with was the transactional nature of conversations. It’s not harder to communicate, but most dialogues happen with an end in mind. You expect to hear some progress, chat about a new initiative, critique a design, get a raise, etc.

There’s no spontaneity. You “grab a coffee” with someone by scheduling a break in the calendar. There was a weird feeling of losing my social senses which is detailed next.

I thought working remotely will make me less sociable.

Me becoming less sociable is the half-truth. It was also paired with the fact that I’m not a huge extrovert and COVID was a real issue.

The pandemic showed me that it’s not always a bad idea for a hard reset. I lost friends, or better said, acquaintances. We could hardly go out or maintain superficial relationships. Everybody focused on what and who was important to them. I did the same, realizing that improving my work, myself, and keeping my circle tight is the best way to go forward.

At first, remote work seemed empowering and natural. It’s easier to focus on your work when you are alone. There was no commuting, no trams running late and I could get started as soon as I wanted.

Remote is great for deep work, but not always ideal for creativity. I tended to keep staying at home, trying to work, thinking that only work will bring me closer to my goals.

And that’s not at all correct.

It’s when I took breaks, ran, walked, wrote, stood, read, and listened to music/podcasts that my mind cleared. But that’s way harder to do when your workplace is your home. For some it doesn’t work at all, that’s why it was hard accommodating to remote work.

I was the opposite. Step by step, I understood the importance of going out, being the one that organizes activities, or signing up for meet-ups and coworking spaces. I seek these kinds of activities as they bring some creativity or relax the mind. And they are needed (for me) if I want to work remotely.

I was never the most sociable person. I enjoy good conversations, but I’m rarely the person to break the silence or start speaking with a stranger.

I don’t think remote work made me less sociable but it helped me see what works for me in terms of relationships, creativity, and serendipity. When things weren’t going great I didn’t want to be alone. I felt that loneliness is dragging me down and it was way harder to deal with it all by myself.

If the trend of remote/hybrid working continues, we could see more coworking spaces being open or just friends renting out a place and working together. It could be the best of both worlds: maintaining social interactions while you work with people that can’t physically be there.

I later found out that many of my concerns fell under the umbrella called impostor syndrome.

You dream of creating awesome designs, working with great teams, and impacting thousands of lives. We all have similar goals so we start designing on our own. Your initial projects are self-started with whatever ideas you have then.

But once somebody actually sees value and purpose in you, doubts creep in. That’s when the real growth as a designer (or person) starts.

Advisable was special. It removed some myths, gave me accountability, and surrounded me with a team that honed my growth. And we had lots of fun.

The opportunity from Advisable came as a huge surprise, but it set a really high bar for what I would expect in a start-up.