A Thoughtful Diary

Thoughts on what it’s really like to start a business, from founder Daianna Karaian. The good, the bad and the in between, as it happens.


Sailing through the mixed metaphors of start-up life

11 December 2016

thoughtful diaryA few months ago, I became an explorer.

Realising how much starting a business is like going on an expedition—venturing into unexplored territory on rough seas with notions of changing the world—I decided to do the responsible thing as captain of this ship. I could see clouds gathering, felt I was going in circles, and was exhausted. I needed to find a port in the storm, a safe place to rest and regroup.

Looking back, I may have been crossing the trough of sorrow. After the highs of setting off on a quest to find fame and fortune, come the lows of the long haul. Sailing into the unknown is exhilarating, until you realise you don’t know when, where, or if you’ll ever land.

I took some time and space to regain my strength, to redraw my map.

One summer afternoon, feeling calmer, I looked around me and noticed there was something familiar about this port. It looked a lot like the destination I was so desperately seeking off in the distance—warm, friendly, stable. It was a community. It was the thousands of people who followed me to the same metaphorical shore—signing up to the newsletter, visiting the website, following on social media—to see what was up with this little dinghy called Thoughtful.

Not only did I find comfort in this community of thoughtful, creative people, I found strength and direction. With newfound energy, I brought aboard some of the most talented and good-natured people I’ve ever met to embark on a new adventure: creating an outstanding digital quarterly magazine. We wrote thought-provoking stories, ran local events and launched global projects. We made things that made a real difference, and inspired others to do the same.

If there’s one lesson I’ve learned in 2016, it’s that you are what you do. Our thinking plays an important role in shaping our worldview, and our words can heal or harm. But it’s actions that really define us. Actions change the world. I hope that 2017 will be a year of action for all who feel adrift in a world lurching toward intolerance, cruelty and division.

I, for one, have big plans. There’s still much work to be done on the good ship Thoughtful, and I’m more excited than ever to do it. Maybe excited isn’t the right word—more like determined, in a gritty, dogged, resolute kind of way. This quote from an unknown source caught my eye recently…

The devil whispered in my ear, “You’re not strong enough to withstand the storm.”

Today I whispered in the devil’s ear, “I am the storm.”

Whether it’s the steady wind of fighting for progress, the rolling thunder of peaceful protest, or a flash of light that suddenly reveals the truth, when the sea is looking rough, better to be the gathering storm than a ship listing on the waves.

Thoughtful crew, we are the storm. See you next year.

This post can also be found on, and shared from, Medium. Sign up here for more.


What it’s like to discover the future

31 July 2016

I once had a fish named Sir Francis Drake.

At school I sat in a rapture as my teachers lectured about Christopher Columbus, Lewis and Clark, and Captain James Cook. I assumed I’d be an astronaut when I grew up, exploring the furthest reaches of space.

But I never made it to Space Camp. The urge to explore faded. I enrolled at university, got a desk job and went about the usual business of growing up. Then, last week, it hit me. Without thinking, without even noticing, I’d become an explorer.

The realisation came after feeling lost for a month. A scary vote just took place in Britain, with an even scarier one looming in the US. Thoughtful was hitting snags. I was tired and worried and fumbling toward what felt like, at worst, darkness, and at best, the unknown.

If ever a band of passionate, creative, generous people was needed to map out the contours of a brighter world, it is now.
But when has charting a new path ever been easy? Anyone who’s ever ventured into unexplored territory has done it with only the most rudimentary map, unsure of what they’ll encounter along the way. Some days it’s calm, glorious sunshine and the wind in your sails. On others, it’s stormy weather and choppy seas, with headwinds blowing you off course. Sometimes you confidently go down one route only to find you need to change direction, then change direction again.

It became clear that building this business is a lot like going on an expedition. I started Thoughtful to test my limits. I started Thoughtful to change the world. And if ever a band of passionate, creative, generous people was needed to map out the contours of a brighter world, it is now. My journey is to discover the future.

In the past year, with a little dinghy, a big ambition and a determined captain, Thoughtful has amassed a crew of over 3,000 likeminded creators from all over the world. So I’m building a bigger boat—one that has room for all of us, and many more, that’s better equipped to make the most of our talents and desire to find a better way.

I’m more ready than ever for this adventure. Am I nervous? Of course. Am I excited? And how. The thrill of going where no one has gone before, the awe of every new discovery along the way…

Right now, I’m preparing the vessel and plotting a course. When it’s ready to leave the shore I’ll be asking you to come with me. I hope you’ll accept the invitation.

This post can also be found on, and shared from, Medium. Sign up here for more.


Think before you […]

2 July 2016

thoughtful diaryI stayed up all night.

I kept dozing off on the sofa, but I couldn’t go to bed without knowing the result of Britain’s EU referendum. At around 4:40am, that result came.

I felt sick. I felt broken. I felt distracted and lost the entire next day. I still kind of feel it.

I knew I needed to get it together and get to work. I knew I needed to keep calm and carry on. I still mostly know it.

But I won’t move forward just for the sake of moving. That would not be thoughtful.

So I am going to pause… to think about how this growing movement of creative, forward-thinking and compassionate people can grow its influence and impact in a world that sorely needs it.

Because it’s not enough just to react with emotion. And it’s not enough just to hope that someone will fix what’s broken. It’s what we do, the way we behave, that makes a difference. If this last week has taught me anything, it’s that each one of us has the power to change things.

But we can’t act just for the sake of acting.

You might hear from me soon. You might not hear from me for a few weeks. But I will be here, listening, healing and planning. And soon I won’t just carry on—I will be back with renewed energy, effort and determination to change our world for the better. Meantime, if you’re curious what’s next for Thoughtful, say hi and let’s talk.

This post can also be found on, and shared from, Medium. Sign up here for more.


The creative (and destructive) power of identity

19 June 2016

It’s true what they say.

When you start a business you’re constantly learning. About how to tell your story, or how to operate accounting software. But by far the most rewarding thing has been learning more about myself; my strengths, weaknesses, what’s really important to me and, above all, who I am.

So, who am I?

The easy answers: I’m a woman; I am Hispanic; I was born and raised in the US; for more than a decade, I’ve called the UK home. But none of those things are ‘who I am’. For me, there’s something more important when it comes to my identity.

Who I am is why I’m here.

thoughtful diaryI’m here to help people who make things to make things better; and to help people who buy things to buy better things. Those things can make a real difference in the world and in people’s lives.

I am not a hippie or a tree hugger. I’m a passionate pragmatist. I’m no activist or campaigner. I am a quiet rebel.

I don’t believe that profit and consumption are the root of all evil. I think we should make money by doing good, and live the lifestyle we want while changing things for the better. That’s what drives me. More than anything else, that’s what describes my identity.

Goodness knows, if I identified as a minority, or an immigrant, or a woman, or even as one of the enviable nationalities I hold, I’d have a lot to feel bad about these days. But instead, by pinning my identity to the most important change I want to create, I’m driven to listen, learn, understand and explain that vision to others. Anything else is distracting.

By pinning my identity to the most important change I want to create, I’m driven to listen, learn, understand and explain that vision to others. Anything else is a distraction.
Paul Graham, one of the founders of startup incubator Y Combinator, wrote in 2009 that “people can never have a fruitful argument about something that’s part of their identity.” He was talking about religion and politics, and about how you’re more open to discussion and, as a result, have better ideas, when you “keep your identity small.” He concludes, “The more labels you have for yourself, the dumber they make you.”

At a time when blind anger and viscous rhetoric seem to be spreading like a disease, I tend to agree. But this doesn’t mean having no identity. As the old adage goes, “If you don’t stand for something, you’ll fall for anything.”

Teacher, leader, maker, healer, parent… you certainly don’t have to start a business to figure out who you are and why you’re here. Identifying the most important change you want to create in this world, in this life, and making that the cornerstone of your identity has tremendous creative power; but only when you’re willing to invest the time, energy and effort it takes to use that knowledge productively in a way that makes us all better off. Anything else is destructive.

The meaning of those other wise words—“Be the change you wish to see in the world”—has never been so clear.

This post can also be found on, and shared from, Medium. Sign up here for more.


Wearing my heart on my startup

5 June 2016

I’m turned inside out.

All the dreams and beliefs I used to hold inside until it felt safe to share them are out there now, all the time, for everyone to see. The trouble with starting a business so firmly rooted in who I am is that I feel really exposed.

What if people don’t like it? What if they don’t respond to it? What if it fails? Replace ‘it’ with ‘me’ or ‘I’ and you’re listening to the little voice in my head. When, inevitably, something doesn’t quite work out as planned, it’s hard not to take it personally.

But it’s worth it.

I’ve been wearing my insides on the outside and hoping others find value in it. That can feel awkward and vulnerable. But it's worth it.
Never have so many incredible, likeminded people been in touch, offering their support or asking to join forces. The quick visit to Sophie Howarth’s pop-up shop that led to a memorable meeting over a long walk in the park. The short comment on a Medium post by Edlyn Yuen that paved the way for a transatlantic collaboration. The tiny act of kindness that, years later, made me realise there’s nothing more gratifying than finding out someone you admire thinks you’re pretty swell too.

From Cape Town to Vancouver, people I have yet to meet in person have become close collaborators and contributors. From New York to Melbourne, people are spreading the word. Here in London, I’m surrounded by some of the most thoughtful people I’ve ever known. Friends have become partners, and vice versa. As the size of the challenge increases so, thankfully, does the size of the community.

“Community” can be a dull word in our digital day and age. But at its best, it’s what you call a group of people you feel comfortable being yourself around. These are the people who ‘get it’ (and get me) enough to help answer tough questions, spark new ideas and share the load. I’m humbled by their interest in Thoughtful, and in the person behind it.

I’ve been wearing my insides on the outside and hoping others find value in it. That can feel awkward and vulnerable. But when you realise how much easier this makes it for kindred spirits to find you, from across the room or thousands of miles away, it just feels right.

This post can also be found on, and shared from, Medium. Sign up here for more.


How to cope with the blob

22 May 2016

Before Thoughtful was anything else, it was a blob in my head. A big, beautiful blob.

thoughtful diaryIn my mind, it was reasonably clear what I wanted this business to do. I knew what I wanted to achieve, and how I would go about doing it. But whenever I had to put the idea into words to explain it to others, things got mixed up.

Nice person: “I hear you’re starting a business. How interesting! What is it?”

Me: “Well, erm…”

Then I dumped the blob on this nice person—a mass of carefully crafted expressions mixed in with plenty of vague, unfinished phrases. This was met with, at best, a polite “Oh.” At worst, a blank, baffled stare.

Did they not see how beautiful my blob was? Was it too blobby?

This was frustrating and worrying. And, apparently, totally normal.

When you’re starting something new, especially when it’s not something most people know, like a restaurant or video game, it’s hard to put into words.

When you're starting something new, it's hard to put into words.
In the year since Thoughtful went from a side project to a full-grown business, I’ve tossed lots of things into the blob, and taken loads out. Through terrifying trial and embarrassing error, I’ve learned which bits go together to form something sensible, attractive even.

thoughtful diaryBut the most basic bits don’t change. Years ago, before Thoughtful was even called Thoughtful, I wrote down the vision for it on a scrap of paper while waiting in a queue at the bank.

Almost word for word, that vision has stayed the same. But how I achieve it has changed, and will continue to evolve, in word and in deed. Call it pivoting, tweaking… it happens to the best of us.

It’s brutal when you’re explaining your own beloved idea to someone and not quite hitting the mark. But it’s inevitable and important. On the web site, in the business plan, at the dinner party… each is a chance to shape the words and ideas until they’re less blobby. And that’s a blessing for me as much as anyone else.

This post can also be found on, and shared from, Medium. Sign up here for more.


This isn’t all unicorns and moonbeams

8 May 2016

I have a confession to make. I’m scared.

To start with, I’m scared to write this. It’s a little unusual to admit to the world you’re scared. And maybe there’s a reason for that… maybe it’s not a good idea. But let’s go with it.

I’m scared because a year ago I decided to dedicate my mind, body, heart and soul to starting a business. No regular salary, no pension, no team… at the time, not even a business plan. Just an idea and some stories on a website. This website.

It was a little scary, but mostly it was exciting. No office, no commute, no boss! No responsibilities or expectations other than those I placed on myself.

The truth is building a business can be scary, exhausting and lonely.
What I didn’t realise at the time is that I tend to place rather a lot of responsibility and expectation on myself. More than any boss ever did. Because this isn’t just a business, it’s my business. And although the buck stops with me (and that’s amazing), it means I have no one to blame, no one to argue with, no one to resent but myself when something goes wrong (which is less amazing).

And stuff goes wrong. Not all the time, but more than the startup books, how-to blogs, high-energy meet ups and inspirational speakers would have you believe. Most tales of screw ups and set backs are told in retrospect, as the preamble to success. It’s something I hadn’t anticipated, and for a while I thought I was the only one finding it hard.

But the truth is building a business can be scary, exhausting and lonely. Rather than try and make it through the tough bits alone, I’ve decided to share it all—the good, the bad and the in between—with you, whoever you are.

This is the first of many scary (for me) and revealing (for you… maybe for me too) posts as I reflect on what it’s really like to start a business, as it happens. Because, wonderful and magical as it is, it’s not all unicorns and moonbeams.

This post can also be found on, and shared from, Medium. Sign up here for more.