Interested in starting your own entrepreneurial journey in personal development but unsure what to expect? Then read up on our interview with Taylor Wilkins, Founder of The Tailored Quill, located in New York, NY, USA.

What's your business, and who are your customers?

I run a life coaching company in which I guide people to tear up their limiting beliefs and self-talk, define their life purpose, and learn how to express themselves with confidence in any and all areas of their lives. I work with people between the ages of 26-40 who feel lost, like they don’t know what to do with their lives, and who are harshly self-critical about their personal values.

These are people who have been conditioned to stay quiet but who want to find their voice and make an impact doing something that is uniquely fulfilling to them. My service has predominantly been 1:1 coaching, but I have also created group coaching programs, an online membership of private workshops and group calls, public workshops, and online courses. I also produce content for a blog and a podcast, and I absolutely love public speaking.

Tell us about yourself

I have always been obsessed with the mind, finding one’s true self, and what it means to be human. As a result, I studied Neuroscience, Psychology, and Philosophy in college. After treating myself out of an unexpected bout of serious depression. I turned my experience into an extracurricular research project, interviewing professors and finding scholarly articles to learn exactly what my body, mind, and spirit had just gone through. After learning about my mental health in such extreme detail and realizing how fragile but fascinating the mind is, I became interested in helping others explore their own minds and subsequently improved their mental health.


The first half of my career was in crisis stabilization mental health treatment programs, helping children first and then adults, most of whom were in acute crisis or suicidal. It was in one of these programs that I first developed the counseling approach that I currently use in my business. I knew in High School that I was interested in having my own business, mainly for the creative freedom and independence it.


In college, I considered a couple of product-based business ideas, but in 2015 I took the leap when I helped a friend write and practice a speech, and she encouraged me to charge people for it. So, I started my company helping clients find their voice in writing and public speaking projects while underneath still using therapeutic methods to help them overcome their expressive and creative insecurities.


Over time my service evolved to strictly therapeutic life coaching, still helping clients find their voice and confidence and express themselves in new ways, but not in a manner limited to creative projects. Using a method I created, we define their actual life purpose and let that be the north star for overcoming feelings of aimlessness and anxiety, finding what makes them unique and awesome, defining more fulfilling career directions, and/or starting businesses that are aligned with their talents and interests.

What's your biggest accomplishment as a business owner?

Staying humble enough to continue growing my skills as a coach so that my clients continue to learn new things about themselves and achieve new breakthroughs. Entrepreneurship is a painfully humbling choice of career path, so I am glad that I have been able to improve my coaching and counseling skills on my own without becoming complacent or resting on my laurels. Going full-time with my business in 2018 was only possible because I knew where I needed to improve and what I should focus on.

What's one of the hardest things that come with being a business owner?

Similar to the previous answer, having the humility to remember that no matter how you ultimately grow your company, at least for a time (7.5 years, in my case), you are your own boss, intern, marketing department, sales team, and administrative assistant and as such it is your fault if X, Y, and Z don’t get done, if you burn out, if your schedule isn’t healthy, if you are not fulfilled.


Along this line, being honest with yourself about what is the hardest thing for you in your particular business is a real challenge in itself. For example, I am more so an introvert by nature, and my business is built on 1:1 relationships and the intimacy of deep conversation. Humility, as I’ve mentioned a couple of times, is important to me, so marketing and self-promotion have always been very challenging. I have had to come to grips with that and test a lot of different marketing methods to figure out which one is best for both my personality and my audience.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. If you have an idea or an interest in something that could become a business, go out and test the smallest version of it immediately. A lot of hopeful entrepreneurs are perfectionists and think they have to have the product perfectly nailed down and all business systems in place before they announce their business, and that is totally not true. I spent at least six months delivering my first version of a service to clients (and they paid me for it!) before I thought once about making a website, a name for the business, or any kind of sales system. A friend of mine casually sold her paintings over the last year and just started to make a website now that she knows people will buy her art. Once you have a little baby product or service to start with, you can start earning money for it, and you’ll find out as you go what else needs to be in place for your particular kind of business.
  2. Marry yourself to your purpose, not your product. I have always been married to my love of self-exploration and helping foster others’ self-awareness, but I have never been married to how my service is offered. This has let me continually modify my offerings over the years and given me the freedom to experiment with as many new versions of it as I want (such as online courses, a membership, and a new payment model during the pandemic). As long as self-exploration remains the goal and focus, I can change my products, services, and business model as many times and in as many ways as I want to and still be fulfilled.
  3. Every step of the way, ask yourself what you want to commit yourself to. If you are not honest about how far you want to take your business or about your interest in being an entrepreneur at all, then you will burn out, and your customer service will suffer. Literally, check yourself before you wreck yourself. I ask my clients and myself this question all the time, and yes, it connects again to the importance of humility and honesty. People, interests, and ambitions change, so there is no shame in closing a business or turning it back into a side hustle if you lose interest in making it your career.

Is there anything else you'd like to share?

Only focus on what is most important for your specific business and healthiest for you in a given moment. Do not overwhelm yourself with everything that experts in the business world are telling you to do. Across my entrepreneurial career - especially during the pandemic - I have read way too many books, watched WAY too many webinars, and absolutely spent too much money to learn from other entrepreneurs what they think the one thing is that I need to do to make tons of money.

I became so overwhelmed by the million things I COULD be doing for my business that I could not tell what to actually sit down and do. Remind yourself what your core service is and why you started offering it (for me, coaching people to find meaning in their lives via self-exploration because I am an ultra nerd about self-exploration) and focus on doing that (because customer service always needs to be first priority) and then only seek out a book or an expert’s webinar when you want to learn about a specific thing your business needs.

For example, look up Dean Graziosi when you need help with sales or Gary Vaynerchuk about social media content. Overwhelming yourself with what experts are saying you should be doing is a recipe for feeling like you are doing everything wrong.

Where can people find you and your business?

Website: https://www.thetailoredquill.com/
Instagram: https://www.instagram.com/thetailoredquill/
LinkedIn: https://www.linkedin.com/in/taylorwilkins3/

If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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