When a long-time solopreneur learns to delegate

Item: Oceans Talent
Author: Dan Oshinsky

1st

hire in five years of solo work

100+

companies served

Industry

Agency

Company size

Startup

Role

Executive assistants

Published

June 21, 2024

Work-life balance

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Inbox Collective is a consulting firm that helps brands grow audiences and build relationships via newsletters. After being the Director of Newsletters for The New Yorker and Buzzfeed, Dan went out on his own in 2019 to form his one-man-shop.

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For five years, Dan worked as a solopreneur with over 100 companies through Inbox Collective.

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However, things began to change when he and his wife welcomed their first baby in July 2023.

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It was never a 100-hour working week for Dan, but suddenly, small luxuries like prepping for the week ahead on a Sunday evening or getting some writing done while travelling were no longer available. Constantly moving between being a present father and husband while also being solely responsible for his work was getting harder, and it was evident.

I’ve thrown her several big projects, most notably trying to take the myriad Google Sheets I’ve been using to track client work, and turning it into a new system to keep track of work and invoices. We’ve got regular check-ins going, and a good system for coordinating on tasks via email at the end/start of my day.

Dan Oshinsky

Owner

Reflecting on what wasn’t working

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Dan had a habit of conducting quarterly reviews and in January 2024, after a look at Q4, he had to admit to himself that despite getting through it, the experience of being a full-time solopreneur, dad and husband, had not been enjoyable. Although he’d heard of friends hiring executive assistants to work remotely from across the world, he didn’t feel entirely comfortable with the idea of getting help that he felt wasn’t fairly compensated for. Through other founders, he learned there was another option: outsourcing that can be done with integrity and care. He found Oceans.

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When Dan first made his inquiry, he learned that he’d be connected with some of Sri Lanka’s top-tier talent and unlike most outsourcing companies, this talent was compensated well, treated well, and deeply valued. To Dan, this meant being able to work with a capable professional he could now trust with delegating some of the tasks that had been piling up in the last 7 months. This also meant he could go back to dedicating his time to doing his job more efficiently while being present at home.

The Right Hand to the Founder

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In February 2024, after struggling to accept the difficulty of juggling his roles as a writer, business owner, dad, husband, and friend, Dan dove into a solution with Oceans. Albeit reluctantly at first, it was time for Dan to delegate!

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In order to find the most compatible candidate, Oceans went through a number of profiles until Nataasha Hallaldeen. With almost a decade of experience, Nataasha was well-versed in handling operations, with the added benefit of being highly skilled in the world of digital media and SEO. Something that Dan saw would come in handy at Inbox Collective.

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Dan suddenly now has the time to spend a couple of hours in the morning with his son.

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Instead of spending unreasonable amounts of time on day-to-day administrative tasks like invoicing, dealing with contractors, getting bills paid, Dan suddenly now has the time to spend a couple of hours in the morning with his son, head to his office space to work with clients and return home in the evenings to truly be present for his wife and child. Nataasha was now taking over projects that helped run the business smoothly while Dan could focus his energy on his clients and the writing he loved doing most. With her help in reorganizing jobs that were previously left to the last moment, a huge weight was lifted off Dan’s shoulders.

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As time went on, he was able to add more value to Nataasha’s role, trusting her with bigger projects that leveraged her expertise while simultaneously enabling him to focus on his business goals. As a long-time solopreneur, Dan had to go from doing it all myself to learning to delegate to others. With Nataasha’s help, he’s able to deliver quality work that he’s proud of while being a present dad and husband.

Dan Oshinsky

Owner

Inbox Collective