Interview with Mr. Jake Schogger

Jake Schogger is a qualified lawyer, entrepreneur, author, copywriter and consultant. He trained as a lawyer at City firm Freshfields Bruckhaus Deringer, before leaving the City to focus on providing legal advice to start-ups and delivering commercial awareness and employability events for students (through Bright Network). Jake has also founded an educational publishing company called City Career Series, a commercial/creative consultancy called Fresh Perspective and a luxury bespoke cake business called Whisk & Drizzle, and runs a bespoke career coaching programme for students seeking City careers

Q. Could you tell us a little about yourself and your time at law school? 

I’m a qualified lawyer, entrepreneur, author, copywriter and consultant. I studied Law & Business at the University of Warwick, then the Legal Practice Course at BPP University in Holborn, London. After a brief stint travelling, I trained as a lawyer at City firm Freshfields Bruckhaus Deringer, before leaving the City to focus on advising start-ups and scale-ups on a range of commercial, employment and fundraising matters. I also run an educational publishing company called City Career Series, a commercial/creative consultancy called Fresh Perspective (through which I work closely with high growth enterprises on a range of creative and commercial projects) and a luxury bespoke cake business called Whisk & Drizzle.

I really enjoyed my degree, from the social aspects and my involvement with societies, to the broad mix of modules that I was able to study. My university also provided the perfect springboard for learning how to launch and run a business, which was a really interesting experience that definitely set me up for where I am now.

More particularly, I founded City Career Series whilst still at law school, and have since sold approximately 50,000 handbooks designed to help students secure City careers. My inspiration for writing the handbooks came from my experiences hosting mock interview workshops whilst running the student “commercial law” society (a society that I had co-founded). Students were clearly concerned about the commercial awareness elements of interviews, so I put together a guide based on all the notes I had taken during countless open days, firm presentations and commercial awareness-related events. I gave this out for free to members of the society, and the positive feedback I received encouraged me to develop a far more comprehensive version that covered all the commercial topics that came up throughout my own interviews. And so, the first proper edition of the Commercial Law Handbook was born.

Q. Did you enjoy law school extra-curricular activities such as debates, moots, ADR’s, mock trials, quizzes, etc.? How important do you think such extra-curricular activities were in shaping your outlook as an entrepreneur and author? 

I was heavily involved in extra-curricular activities at university, but more because I was interested in getting involved, rather than specifically to boost my CV. You should use your time at university to at least have a go at all the things that interest you, as many of these opportunities won’t be so readily (and cheaply) available once you leave. I played drums in the big band and a smaller jazz band. I ran a commercial law society and a finance society. I attended government-funded study programmes in China and India. I played football and tennis (I once even attended an American football training session, but the less said about that the better!). And I worked part-time as a drum kit teacher throughout my degree so that I could afford to travel during my summers. On that note, enjoy the long summers whilst you can. Once you start work, you won’t quite believe in retrospect how much time you had off as a student!

If you hit a barrier, try to find a way around it. I was rejected when trying out for the men’s football team, so I set up my own casual 5-a-side team and played weekly throughout university. I was rejected when running in an election to join the law society executive committee, so I co-founded a society focused on commercial law, which meant that I could still experience what it was like to build and run something. Running a society turned out to be much like running a business, from developing, branding and marketing an offering, to recruiting a team, raising funding and carefully budgeting. In this sense, my extra-curricular experiences helped immensely when it came to setting up my first business.

Q. How and when did you realize that the area of consultancy and copywriting is the one for you? Was there a specific incident/person that made you realize your potential for the same?  

I really enjoy writing and had worked very hard on my writing style whilst authoring and editing my books. I have also always been fairly creative (I was in a band for years before going to university in my mid-twenties), so wanted to find a way to write in a more creative way than was generally permitted for legal drafting. Copywriting seemed like a pretty good bet, so I gave it a go. Since then, I’ve picked up such a broad range of work, and it’s the differences in subject matter that keeps it interesting and challenging. One day I’ll be writing about vegan dog food and complex software, the next, financial planning and travel destinations!

I’m also very interested in start-ups and strategy, having tackled many of the challenges faced by start-ups when starting and growing my own businesses. I started spending more and more time drawing on my own experiences to help my clients’ businesses – far beyond the scope of copywriting – which is how my role as a start-up consultant evolved. This more commercial role very much goes hand in hand with the copywriting, as it means I can consult for businesses on the broader commercial considerations that underpin their products and services, then use my copywriting skills to help them to articulate their key messaging.

Q. What was the transition from a law graduate to an entrepreneur, consultant, copywriter and then a business coach like? Looking back, do you think you would want to have done anything differently? What were some challenges that you faced during your journey to follow your dreams and how did you overcome those? 

The transition certainly wasn’t easy. I spent countless hours networking, probably participated in well over 100 calls and meetings whilst trying to find work that aligned with my strengths and interests, and worked hard to remain positive and optimistic. My mantra throughout my transition has always been “opportunities don’t happen, you create them” (a great quote I once read in an Escape The City newsletter), which has kept me proactive and motivated. I also knew I had the focus and drive to work for myself from home, as I had managed to keep the publishing company going (and growing) over all these years, so at least that was one less thing to worry about! 

I genuinely enjoy the freedom of self-employment. However, when you are self-employed, you are reliant only on yourself to bring work in, so there can be times when you worry about your pipeline of work and long-term ability to earn. Luckily I’ve always been a “glass half full” kind of person and believe that if I keep at it, the work will continue to flow, so that’s certainly helped. Some people might also struggle with the lack of human contact, but I spend the vast majority of my days on video calls with clients, which is enough for me from a social perspective (I also get to go to multiple client Christmas parties, which is another added bonus!). 

Looking back, perhaps I would have explored potential careers in consulting and marketing more at university, but being totally honest, I love where I’m currently at and everything I’m doing now is simply a product of my journey!

Q. We are seeing a global trend that more law graduates are entering into the arena of business and entrepreneurship; do you see this trend continuing? Has being a law professional previously helped you in achieving greater heights in this specific career?

I can certainly see that trend continuing. You gain so many transferable skills throughout your legal education and legal training, and more and more lawyers are transitioning into other careers. I have friends that have moved into careers ranging from operations to teaching! 

As a lawyer, some of the truly important skills that you develop include organisational skills (to help you project manage complex legal matters), communication skills (when explaining technical concepts to clients and team members), attention to detail and strong writing skills (to help with legal drafting), team working abilities (as you are constantly working in teams) and professionalism (as clients – and your peers – expect you to be responsive, composed and professional). Resilience is also key to helping you deal with things going wrong when you’re already stressed and tired, not to mention the stream of constructive criticism you tend to receive during your training. I now rely on pretty much every one of these skills and attributes on a daily basis when working for a range of different personalities on an interesting variety of matters, so in this sense my legal career has certainty helped.

Q. What were some of the most important aspects you looked into and took into consideration before the career switch? 

I learned a great deal during my training contract and was lucky enough to work with some really great people. However, by the end of my training I had realised that my own priorities and professional interests didn’t align closely enough with a career in the City. 

Firstly, I decided I wanted more control over my time, a priority that was especially important to me given that my son had just been born. Ironically, I now work longer hours than I ever did in the City, but I like the fact that I have the flexibility to work from home and can guarantee time off when I really need it. I also have far greater oversight over my current and future work-related responsibilities, which makes it easier to plan ahead.

Secondly, I had identified “impact” as another important priority and had discovered that working on deals that made the front page of the Financial Times wasn’t the kind of impact I was after. I wanted to work in a context that enabled me to see first-hand how my personal contributions made a real difference for clients, which is what eventually led to me shifting my focus towards start-ups and my own businesses. This has enabled me to work directly with founders and join a variety of start-ups on their journeys, which makes it easier for me to gauge how my advice and support contribute to their growth and success.

Q. What is your coaching philosophy for life and would you encourage and advise our young enthusiastic readers to follow your footsteps?

I would tell people not to stick with a job simply for the prestige, or because they’re too afraid of re-entering the job market. You spend the vast majority of your life working, so try to find a career (or work towards eventually transitioning into a career) that genuinely interests you. It’s absolutely fine to start out on a structured graduate scheme. You’ll most likely benefit from the credibility for the rest of your career, not to mention the high-quality training that such graduate schemes provide. Just don’t let yourself get stuck if you don’t enjoy it. If you want to change careers, focus on your transferable skills and the value you can add, rather than the industry-specific knowledge you’ve acquired. That’s what I did when rebranding myself (and overhauling my LinkedIn profile!).

If you do want to move into an unknown territory, make it happen. Network like crazy. Put together a portfolio that shows off any skills you’ve acquired that are relevant to your new prospective career. Actively pursue opportunities to meet people and don’t discount people you haven’t yet met. And finally, as mentioned earlier, remember that opportunities don’t just happen: you create them.  

 Find out more about Mr. Jake Schogger – 

Disclaimer – All views and opinions expressed in this interview are personal and belong solely to the interviewee(s) and do not necessarily represent those of the LAABh Foundation or the individuals and institutions associated with LAABh Foundation.

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