As more of us challenge our inherited metrics of success, the question of how to design our working lives becomes more eminent. The multi-hyphenate career is both an adaptation to that question and a necessity for some of us. Though not a new phenomenon, having multiple careers over the course of our lives not only fulfills our creative potential but also sharpens our professional acumen. Rakeb Sile, a seasoned entrepreneur and management consultant, now straddling careers between Google and her prestigious Addis Fine Art gallery, knows this all too well.

“All businesses are essentially the same: they have a big idea which they take to market. Some people do it better than others,” says Sile over a Zoom call. By this point in our conversation, she had convinced me on the value of integrity in business, the entrepreneurial nature of motherhood and her stance on why one should think twice before starting businesses with romantic partners.

With a background in management consulting for the telecommunications, media and technology sectors, and a life-long experience experimenting with business ideas, Sile does business strategy better than most. Recently, she took up a strategy position at Google, while the company she co-founded in 2016, Addis Fine Art Gallery, is making waves on the international art scene. For her work on building Ethiopia’s first white-cube space for modern and contemporary art, she was named one of Apollo’s 40 under 40 inspirational young people in the African Art World in 2020.

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Before the side-hustle generation, you were the OG multi-hyphenate, balancing careers in management consulting, tech and art. What runs through these different facets of your work that helps you balance them successfully?

You can't get away from these two things: things that you really want to do in your life, and things that you have had to do. The confluence of these things is what makes my life. When I was ten, my family came to the UK as political refugees. But living in Ethiopia for the first ten years of my life, with a father who is a true entrepreneur, there was no escaping my wish to do something connected to my culture.

Prior to starting Addis Fine Art (AFA), I had a decade experience in management consulting particularly for the telecommunications, media and tech (TMT) sectors. My job at Google comes from that trajectory. The screeching halt of the pandemic gave me time to think about next steps in my life. AFA had become a sustainable business and so I wanted to move on to something else that would be additive to the work I do with AFA but that would still balance me out as a businesswoman. It’s also important to speak about my personal life because my current entrepreneurship journey didn't start until my motherhood journey. It wasn't until I became pregnant with my first child that I had the time and headspace to put my creative energy behind my long interest in Ethiopia, and in art, which I had been pursuing for ages.

That is interesting because I would have imagined that with motherhood being the very intense venture it is, one would have less time and energy. So how was that journey for you?

I had a great pregnancy. It was during that period that I went freelance with consulting. Five months in, my last contract finished, and I could not get another one, so I was thinking ‘what’s the next thing?’ 

Art was always in the background, not as a hustle but more a passion. I had already spent four years prior to that first pregnancy researching and collecting art and I had found a mentor in Mesai Haileleul, my current business partner at Addis Fine Art, who had worked in the arts for more than 30 years. He had set up a gallery doing exactly what AFA does today, but it was way ahead of its time and so it folded. Mesai and I knew a lot of artists that had no visibility but were doing incredible work with very little acknowledgement, money or accolade. During that pregnancy, the timing finally felt right because African art was really at the forefront of people's minds. It had to be the right time, the right people and enough experience to execute the right idea. 

In that year of creative birthing, I found that I could do things I thought I could not do; I found that we are made to just continually expand and do really difficult things. You hit a wall, and then you break through and then you hit another one and you could continue to expand if you wanted. Being a mother has made me a better businesswoman: it has just made me so willing to just cut the crap.

Starting from scratch is the hardest

Do you find that your work in one facet of your career enriches the others? How so?

With Google, it’s going back to the bread and butter of my career. I work in strategy and operations, so I help with planning, strategy and executing the operations against our plan. The scale and depth are different, but it’s the same thing I do at AFA. I do the short-term business plan, and I operate that business plan by motivating my team, leveraging tools, refining my processes, and always looking to the address of market opportunities.

The reason why AFA has been successful as a business is because I have been able to bring these skills I had from my early consulting and tech days. We are tech-heavy compared to most other businesses in the art industry. The art world is essentially a retail business but with very, very low margins. It ends up being a hierarchical and cannibalistic industry where the bigger galleries just get bigger and acquire more and more artists from the younger galleries. On the other hand, younger galleries do not build enough of a brand, which sometimes is then due to a lack of resources.

To go back to what you said earlier about how a successful multi-hyphenate career depends on the balance between the things you want to do and things you have to do. What exactly has that tension been like for you?

Coming from where I come from, I had to go to university, get a good job, and all those pressures that parents put on us as children from immigrant families to keep us safe and give us the options they think we will lose out on. I’m glad I did so because nobody can take away your education. Going into management consultancy at the time was also an excellent learning opportunity, because it allowed me to see how big companies work. I saw that businesses are essentially the same: they have a big idea which they take to market. Some people do it better than others. Some people do it with less resources, some people do it with nothing. And for the things I wanted to do, I did them with my side hustles. I learned what it’s like to really start from scratch, which is the hardest bit.

How do you see AFA enriching the African Art ecosystem, and vice versa?

Honestly, everywhere on the continent outside South Africa, there are no real ecosystems. If you are venturing into an art business, you are building the ecosystem. At six years old, AFA is one of the only commercial art galleries in Addis and it’s not something to be proud of. This industry is very difficult. There’s no infrastructure, artists have a huge difficulty even getting their basic craft tools and we need more art schools. So, a lot of the work we do now is also advocacy for artists and for the country and continent. With us, you come into our gallery and learn by seeing the diversity, quality and depth of experience from a specific region. And with a country like Ethiopia where there’s a wave of emigration every decade, East Africans have a huge variety of stories to tell from all around the globe.

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In life and in business, scaling up matters 

How have you been able to field the challenges that come from combining your passion for the culture with your entrepreneurial grit?

Yes, we wanted to represent artists. So, the how became important. You can do it on a shoestring budget which was what we did for a while. Unless you are trying to start a charity, or you are just putting money into a business that’s not successful, you have to get to a point where you ask, ‘How do we make this sustainable?’ You have to scale for things to work. Unfortunately, that's just the way life is. And in order to scale and to fulfil that mission statement you’ve created at the beginning; you are going to need investment. Hence, we had to raise funding, streamline and train our staff (who are some of the best trained gallery people around!) It also boils down to integrity; we had a very tight mission which we kept talking about. Three years down the line, we had proved that we could make history and so we were able to find the right investor who matched our vision perfectly.

What do you see as the power of the multi-hyphenate African woman today? 

My dad always told me that in whatever you do, never rely on one source of income. Nowadays, that's not such a huge gem anymore. It’s pretty much everybody's experience with the rise of zero hours-contract and the gig economy. People have to think outside the box, because now the box has gotten so much smaller. You go to university, and then you get a job, but that job is going to underpay you. How do you actually compensate for your expenses? I think young people nowadays are much more entrepreneurial than my peers because they simply have to be. Side hustling is also not just about the earning but the learning too, which tends to be visceral and so the lessons stick. My failed ventures taught me so much more than my current venture or even the decade I spent in consulting. Trying things and failing helps you evaluate why things failed, and over time, you get to understand your strengths and weaknesses and how to collaborate with people to support those weaknesses.

I Surrender My Body to Water and Fire by Daniela Yohannes opens at Addis Fine Art, London on 21 January 2022. 

This interview has been edited for clarity.