A Conversation with Tasheen Thomas

A Conversation with Tasheen Thomas

This post is part of our podcast, “Freeality: What It’s Actually Like to Be a Freelancer & How to Succeed as One.” Freeality is a weekly, ongoing series of interviews with experienced freelancers, where we dive deep into the tactics and tools that helped them build a successful independent career. This post has been lightly edited from the interview transcript for brevity and readability. Do you know someone who would make a great candidate for an interview in this series? Let us know by emailing contact@jollyhq.com.

The guest for this episode is Tasheen Thomas. He's interviewed by Shelby Stephens, co-founder and CEO of Jolly


If you prefer to read instead of listen, the transcript is below, edited lightly for clarity and brevity.


Shelby Stephens (SS): Today we're interviewing Tasheen Thomas, a consultant. Tasheen, thank you so much for joining us today.

Tasheen Thomas (TT): Thank you for having me Shelby. I really appreciate sure

SS: I'm really excited about our conversation and I want to get started by giving you a chance to introduce yourself and tell us a bit about how you started your independent career. How'd you get into it?

TT: Well, first, my name is Tasheen Thomas. I was born and raised in Buffalo, New York. Go Bills. And I started my freelance consulting journey in 2017. I should really say the holiday season in 2016, early 2017. I was just tired of not being able to live my life on my own terms. I felt working nine to five I was making someone else's dream come true while my dreams were sitting on the back burner. And so for me, I decided to go for it, stop apologizing for my dreams and my goals and decided to go out on my own.

SS: So you got started in 2017. I want to know what you're doing today. What services do you provide in your independent career? And are they the same or are they different from when you started a few years ago?


TT: Well, currently I offer sessions in personal coaching because I am a certified life coach. I'm also offering sessions in language-learning, entrepreneurship and musical artist development. I have this background that's multifaceted in studying music, in teaching both music and English, and also (now being a certified life coach) helping people just with day to day life or the transition of one chapter of life to the next.

We have migrated in a very short period of time to doing so many things online. I was already more open to offering services that way, even when I first got started in 2017, because I saw the ease of being able to meet with people, schedule things, and still have the ability to work effectively while not necessarily having to meet in person. But I also did meet with a lot of my clients in person, one-on-one. A lot of times I went to them and worked with them where they were in their homes or their offices, to garner that sense of camaraderie and rapport. But now with present changes, as they are, a lot of things are offered online. So I was already prepared for that.

I would definitely say that for me, I think the biggest thing about Jolly that's so helpful is it takes away the work of having to deal with creating my own website and all the things that go with that. There's so many things as an entrepreneur and as a freelancer you're dealing with on the backend. That a lot of our clients don't know about. So having this platform, it allows me the freedom to continue what I'd like to do and that's create and that's teach and that's help people be the best they can be.


SS: Yeah. That's so interesting. Something I hear a lot from other freelancers is this notion of looking for tools and processes and platforms that can help me spend less time not serving clients and customers and more time doing that. Because it's both what brings me joy, it's how I have a positive impact in the world, and it's how I earn, right?

TT: Yes. I liken it to, Mr. Rogers had this wonderful saying, and he would say, “always look for the helpers” and for independent thinkers and movers and shakers in the world, because we are so focused on that vision, that dream, and we are pursuing it with all that we have. We need helpers to allow us the freedom to express our creativity, to be of the highest service, not even just to our clientele, but to society at large. Because the world is demanding our voices to speak up and out. And it's our creativity. That can be the solution to what is going on in our present world. Jolly is that helper in my opinion. And that's what I've come to find. I'm able to just put my services out there. I don't have to apologize for what I do. I don't have to apologize for the fee that I required to perform those services and I'm not alone in offering that. There's a community of us who are in various niches, wherever we may be, and we all want to offer to the world a high quality service that is of value.


SS: Earlier in the conversation, you mentioned the idea of building “rapport and camaraderie” with your clients, which in many ways you previously did by showing up physically and providing your consultations together, with COVID that's not possible. You mentioned that your transition to providing your services remote has gone pretty well. I'm curious if you can unpack that a little bit, what are some things that you've learned are helpful to you in providing consultative services remotely that help you build that sense of rapport and camaraderie?

TT: I think the biggest part of it, at this time, is as we're using social media and social platforms, is the “being social” part. I don't think there's anything that can replace genuine care and concern for other people. I think that's why many of us who work independently as freelancers, as consultants, as entrepreneurs, we do that because we have a genuine sense of care and we think about the kind of services we would purchase for ourselves. So we give that same kind of quality and service to those people. And I believe that by engaging with our clients through email or text or making ourselves genuinely available to assist them, when different hurdles come up along the way.

For me as a life coach I tell my clients, “listen, yes, we have our sessions and that's great and I love that you are here in the session, but also know that you are welcome to text me and ask me a question about something going on about a process you're working through.” And I genuinely respond in the space and time that I make myself available to respond. I think that touch is something I give because that's what I want someone to do for me. And that is something that is available for me, with people that I'm working with, who are coaching me or counseling me, they make themselves available in that way. And it's wanting to do that because it's in you to do it that helps you build the camaraderie and rapport with people. And then also it makes it easy for my clients to say, “Hey, this is the person I'm working with. You should give him a try,” and that's okay if I meet other people and things work or don't work because I'm confident that what I do is a good thing. But taking that extra step, sending that email, creating some sort of graphic along with some inspirational texture tips or something that's motivating. That's just personal to my community of clients. It's just for them to take in to enjoy it really, I believe, makes a difference.


SS: Yeah, it reminds me of an upcoming guest on this podcast by the name of Justin Foster, who blogs pretty regularly. He recently wrote a post about the difference between striving and receiving. And what you're saying makes me think of this notion of receiving in the sense that just being available is not just a great way to be supportive of your clients, but it's also a way to be receptive to what the world is bringing you and what your clients are bringing you.

TT: I absolutely agree with that, Shelby. I really think that for all of us who are givers and helpers, we also need to equally make ourselves available for receiving that same good that we give out. The same kindness that we are willing to share with the greater community at large. It's so important that in our work, we don't forget ourselves. Sometimes we do because we're in the hubbub of the next goal, the next thing, or the daily agenda. I believe as I was taught to practice what you preach, to practice what you teach, to practice what you coach to your clients. I don't just give this information out to my clients, I first take it in for myself and I ask myself, am I doing those things that I'm teaching them to do? So I definitely agree that it's so important to make yourself available for receiving just as much as you give. And I know for me as I've done that, it has been wonderful to know that there are people out there that are willing to do just as much for you as you are for them.


SS: What advice would you have for other folks starting out in their independent careers, specifically around finding those types of people? I do agree with you that there are folks out there like you described. Maybe reflect a little on your own experience early on in 2017, when you were starting out. How did you find those folks who were willing to give to you and help you in that time?

TT: For me a big part of it was being intuitive. I think for us as creatives, we know what the next thing or the next right thing is we should do, we don't act on it all the time. And so if you know that being independent is the next right thing you should do, plan to do it. Plan to do it appropriately in the context of your life and your circumstances.

I would definitely say in reaching out to people, look at your network. Look at who pays attention to what you're sharing and what you're posting on Social media. Not only are those people interested in what you're saying, there are people in their circles who may be interested in what you're saying too. Always think about the next few steps ahead. It may not just be the 10 people around you that could benefit from your services, but think about the 10 people each of them know. I would definitely say to be confident about what it is you have to offer, because if the intention is that you have something to offer that is good, then there are good people out there who have a need for you and a need for the service that you're offering. So of course plan, be intuitive, but most importantly be confident and do so knowing that the right people will come along as you share what you're offering and as you work with people and they go and tell others.


SS: I'm reading a book right now that was recommended by a prior podcast guests named Maggie Gentry. The book is called Crossing the Unknown Sea by David White. And I try to wake up early in the morning and read some before my kids wake up. And I want to read a part of what I read this morning and ask you a question about it. So in this passage, David White is writing about the process of deciding to follow a path that you feel called to follow. You described your experience in 2017 earlier in this conversation as well, I can't remember exactly how you described what you were feeling, but it had something to do with following your own dream. Can you remember how you described that?

TT: I believe it came out of just being tired of pursuing someone else's dream. I also was nervous and afraid, but I was more so tired of doing for others and wanting to put that energy into myself.

SS: Yes. Awesome. So kind of thinking about that time and that experience, and also the advice that you were just giving just a moment ago. David White is writing about this process of sensing that you should follow a new path and what that feels like. I'll read this passage. He said, “...besides the reasons not to follow your particular Pilgrim path, are there in magnificent quantities. If you ever want ammunition to shoot down any secret ambition, ask others in an abstract kind of way, what they think of your plans. We keep the most precious things secret exactly because we're not sure they would stand up to the scrutiny of light.” So he's a poet and he's talking about pursuing his path as a poet. And he says, “if you want to meet terrifying silence, tell the world you're going full time as a poet.” And I laughed out loud when I read that the first time.

So, how did you face that? When you were deciding, “okay, this is what I'm going to do,” having the courage to do it in many cases starts with having the courage to tell people that you're going to do it. So how did you overcome that? And if you were working with someone who's also struggling to make that transition or to get that courage, what sort of advice do you give them?

TT: I framed it to my family as working from home. I didn't say that I was going to freelance or start my own practice or start my own business, I just framed it as working from home. And the response I got was a lot of attitude “Oh, well, isn't that nice” or “Oh, Whoa. Look at you. Just being able to work from home,” a sense of bitterness that I was doing something that they wanted to do, but they weren't really sure of how they could do it too. And all the while I'm not really sure how this was going to work out either. I was just feeling like this was the next right thing for me to do, the entirety of the path wasn't laid out.

I also discovered in that moment that I've been here before, because I went to college and studied music and a lot of people in my family didn't agree with me studying classical music and opera as a course of study in college because they didn't see the usefulness to a degree in music. And they said, “well, what would you do with a degree in music?” And I forthrightly believed that I would be a professional musician, something I still have yet to discount in my list of dreams. Because I've experienced that before, I knew what it was like to feel like an underdog and to feel discounted and for people to not believe in what I wanted to do or to dismiss it as if it were child's play. And I also knew that it was good that I didn't expound upon the entirety of what I wanted to do, because if I had I fear that all of my dreams would have been shattered and I would have been right back in some sort of office working nine to five again.

At the end of the day, I chose me, in both of those circumstances. I chose me because I thought that me, Tasheen, was a worthy cause, that me, Tasheen had something incredible to offer to greater society. At that time, I was still figuring out what that was and on the journey that is changing for me, which leads me here to being on Jolly because I find myself moving in a new direction, which I'm okay with and I'm comfortable with. But I would say to the person who may be listening and is unsure if this path is for them, that it's okay. It's okay to walk down a path that you don't know every step of, you don't see every little brick along the path laid in front of you. It's okay that you're doing something that you have not seen others do before you, it's why it's called being a trailblazer, it's part of the journey.

Most of all, I would encourage anyone who's listening to choose yourself. There are so many people out here who do not have the heart that you have, who don't have the intentions that you have. Why? Because they are not you. You have an incredible gift to offer the human family. And if you're listening to me today, I would encourage you to go. Go with the light within you and create and make a platform available to receive people who want to learn what you have to teach. Choose yourself because you are a worthy cause, choose yourself because no one can do what you do better than you.


SS: Wow. That's some powerful stuff. I want to ask, on this path where you don't know where the next brick is going to be laid or which direction it's going to go, I think an independent career is like that in its entirety, right? It's not just at the beginning where you're choosing a path that's leading to an unknown destination. The whole thing is like that. You may never know the destination. And I'm curious in your experience, what are some of the things that you listen for, that indicate to you that the path is changing or that a new direction might be presenting itself to you?

TT: I'm always paying attention to the trends in the sense of not the minutia or the micro of it, but the macro of it. We're moving into a stage where the majority of young people in our country today are learning remotely or in some sort of hybrid format. And in 2018, as things were picking up for me, I was sharing with my younger brother, TaShawn, who I consider to be a confidant and one of my best friends. I was sharing with him, just how I felt the world was changing, how we're going to see more of our children being homeschooled and the public school system, having to figure that out. How to educate our kids on a massive scale using technology. Here we are in 2021 and our public school systems are now being forced to adapt in a very immersive way into the 21st century.

So much of our business is being conducted online. You can be based in a city, you can be a nomad, if you will, and travel to different locales around the world and your clientele can be based all around the world. I live in Buffalo, New York, I could have a client that lives in London, in Sydney or on the other side of town where I live. But the comfort of knowing that all I have to do is meet them at the computer or on the phone and still get a great deal of work done. It relieves so much anxiety for a lot of people, especially as we are in a society that is choosing to take on mental health and make it a priority in the global community.

Those things were, to me, making themselves present two and three years ago because I was moving in that direction because I just felt that that's where we were going. I mean, we were using social media as a motive to market and advertise in a lot of ways without paying for it. We're using emails as a way to send newsletters, to family and friends, to tell them about what we're doing, what's going on, how certain seasons of our life are going. A lot of us would do it like at the holidays to talk about Christmas or Hanukkah Kwanzaa. But now we're sending out email newsletters to offer our services, to talk about digital products, physical products, I mean, whatever. And we're sending these emails out by the millions and billions to people all around the world. Our world has become so much more entrenched in technology and I'm choosing to see the good in it. No, it's not perfect. No thing is, that is okay. But I saw it two or more years ago, that that was the direction we were moving in. And lo and behold, here we are.


And now so many people whose names who probably wouldn't have been known are known today because of technology. People are famous today because they are influencers on social media or now being a YouTuber is an occupation, it is a profession, albeit greater society may not always understand what that is or what that means. But now we have these new terms that we are now integrating into our lexicon as occupations that allow people to live a healthy, wholesome, free life. I'm looking now to the future where I see e-commerce and even Jolly being at the forefront of where so many people like myself who have these premium services to offer, having that marketplace that one location, because that's what people are attracted to-one place where they can go and get what they need and, move it along. And what a wonderful thing that will be for us to find that coach, find that teacher, find that instructor, find that graphic designer, find that writer and everything I need to know it's on the page. It's there. How to connect to them on social media, what services they offer, what courses they offer. And it's there and you make your choice and you connect with them and you keep it moving. I believe Jolly is the future and it's the future right now, here, in the present time.


SS: Well, of course I share that sentiment and I appreciate you sharing it because that is very much our mission is to build what we hope is the future of empowering independent freelancers, consultants, entrepreneurs to offer whatever it is that they feel called to offer to the world.

I want to ask a question about values. I think about personal values in a really specific way, largely inspired by some of the work that a group called Human Systems has done. They think about values as approaches that we take to improvising as we live our lives, approaches that we take that result in us having a meaningful experience. I want to ask when you approach your work with clients, when you approach thinking of new services that you could offer, what values are important to you in terms of approaching your independent career, such that you have a meaningful and rewarding experience?


TT: For me, I would definitely say it has to be bicameral. It has to be beneficial for both me and for the potential client. Right now in this new year I am working on developing courses because the services that I have to offer as far as one-on-one and in-person are the full gamut for me of what I can offer as an individual offering services to one person. I'm thinking about now helping a larger scale group of individuals while also not having to be physically tied to my computer or to my desk. I also want to offer them the kinds of information that will be timeless and always relevant and universally true.

But also for me, it maintains my level of freedom and quality of life. I've been able to have a quality of life where I can really spend time with my family. Like money is great. It's wonderful. I appreciate it immensely. But the time that I have, like when I finish with I will go upstairs and I will bake a ham and I will make a brown sugar glaze to go on that ham. And I will enjoy the rest of my day because I have no other appointments scheduled for today. And I have that free time to say, at this point in my life cause I'm not tied to a desk I'm not tied to a punch clock in any way, shape or form that I can just enjoy being with my family. I can enjoy the conversations that I can have with them while I'm cooking in the kitchen or I can talk to my friends on FaceTime or Instagram or whatever.


TT: But I believe if the services I offer have maxed me out, personally, on one-on-one working time. I definitely feel that I value being able to give and offer something of high quality, and that's what I want to create in this next step for myself in the courses that I want to create. But also the students that will enroll in those courses, they also have the freedom to integrate what is being taught because sometimes you may work with me for a month and yes it will be impactful, but there are some things that may not hit or you may not click with right in those four or five weeks we're working together. You may need to go back to a lesson that I've recorded and be able to say, “you know, now that concept he was talking about, I think I can integrate this now. And it helps me create a sense of relevancy and timelessness that goes beyond. Just the offering of services.” I think it's why I'm seeing the fun and creating content again, because there are people now who are liking posts that I created six months ago because they're scrolling and they're looking at my profile and they're like, “I didn't get that when he first posted it, but I get it now. I like this now.” And realizing that all the work that we do in the moment, it's not always for the present moment. At a lot of times, it's for the future.

Even in the moment this podcast will resonate for eons because there will always be someone who wants to hear about what can I do to get started or how can I put myself in a position to transition from being a W2 employee to an independent entrepreneur, because every day someone is making that decision. And I want to be in a position where every day someone is deciding I want to do something different and be that person that has something to offer in the forefront. And maybe you can't work with me one-on-one, but then there's a course, there's content, there's other things available that I can share. And it's aligned with the values that I have of still maintaining my freedom and having my quality of life while offering something of high quality to my clientele and potential clientele.


SS: At Jolly, we have a core belief that true freedom means creating your own rules. And I'm wondering if you want to unpack that, if that means anything to you. Beyond what you've already shared.

TT: That could be the mantra of my life. I could really put that on a t-shirt and wear it every day. You know how some people get to where they wear the same outfit every day. I could wear that on a shirt where I just say “I create my own rules” because I don't like being told what to do. I don't like being told when to do things. I am very much an intuitive person. I'm very much a spiritual person. So I believe in going with the flow, and it does have its counterweight to it, because at times I do want things to happen in a very sudden way and the reality is you have to build certain things or you have to be patient and wait for the right timing for things to occur. But for me, I love the life that I lead right now. I love that I have the time for myself to be the best Tasheen that I could possibly be. I love that I can nurture and foster, not just professional relationships, but my personal relationships. I love that I can foster my own relationship with myself to myself, by personal development and going to therapy and taking care of my self-care and exercise and eating healthy and all of those things. I now can make time for those things in a way where I really feel it in my being, in my body, that what I'm doing is good for me. And so that when I help others and when I step into that role of chief servant to assist and facilitate helping others on the journey, I'm giving them my best because I've taken out the time to give myself my best, but because I chose to create how I wanted to do it.

And for some people, creating your own rules can be scary. That's okay. I'm one who believes that you should feel the fear and do it anyway. That you should go for it because that's where you'll find your freedom. As you step beyond your fear, you will find your freedom and you will realize the joy that comes in truly creating your own rules, stepping into your own potential. And actually just how powerful that is and how much change you can affect in your community, in the world, in society at large.

SS: Well, at some point we'll have to make some t-shirts and I'll make sure to send you one. I also now am going to, I think, forever associate a brown sugar glazed baked ham with freedom. With this notion of having an independent career where I'm able to make my own rules and best be able to have time to bake a ham. So for me, baked ham is now going to be the symbolic food of being able to create my own rules. I love that.

TT: I'm so glad that I could do that.


SS: Thinking back to the very beginning of your independent career, what advice would you give yourself? I know you've already given a lot of advice that I think is applicable, but anything just really clear and specific for that you would want to advise yourself at that early moment of starting out.


TT: I would tell Tasheen back then to take things one day at a time. Everyone around you wants you to think about six months from now and a year from now, and you just need to focus on today and what you can do today and have gratitude for what you know today.

Number two. Tasheen, you cannot build a profitable business overnight. It takes time. One client at a time reaching out, being consistent and being patient with the process.

Most of all, number three. When you get to where you are sometime down the road, three, four years from now, you will look back and you will be grateful that you did what you had to do. You will be glad you left that job, you will be glad you gave yourself a chance, and you were able to put yourself in the arms of the universe and find out what you and the universe could do together.

And everything, as TaShawn would say, “it's going to be alright” all the time to everything. And even in those moments when you find yourself upset, stressed, discouraged, even to the point where you want to give up and just say, “you know what? Maybe it's just better for me to go back to what I was doing,” I would say to him, and I say to anyone who's listening, it's going to be alright. It won't always be bad or stressful or rough or crazy, or whatever adjective you may find yourself filling in that blank with that you're feeling right now. It does get better. There's a community out there that's like you, that understands you that will embrace you. And there are tools out here to help you be the best creative freelancer, entrepreneur consultant, whatever that title is you want to fill in the blank with for yourself, because we do make up our own rules around here. And definitely Jolly is that tool that can help you.


SS: Well, I appreciate that. And before we wrap, we've mentioned this idea of tools. I love that you channeled Mr. Rogers, “find the helpers.” Is there anything else that you want to plug or that you think might be helpful to listeners and readers that are other tools or other helpers?

TT: Definitely. It depends on the person because every business structure and situation is different. I think overall, I would say find the smart people who know how to do the things you don't know. Currently business taxes are a thing that I am not well-versed in, so the time came this year to get to hire a CPA. I would say when you don't know something, find the people who do, like if graphic design is not your strong suit, find a graphic designer. If you don't feel that you're the best at writing, find a writer who's incredible. Do not feel that you have to do this by yourself. If you go at it alone, you're doing yourself a disservice because you have an incredible gift to offer society. And it should not be bogged down by administrative work. There are people who are competent and brilliant and talented in that, find those people who can do those things. I don't know what you may need as far as your business goes or where you are, but find the smart people who know better than you. And ask for their help. There's nothing wrong with asking for help. The truth is you have not because you ask not. I will say this just from my personal experience, after I had my first conversation with my CPA, there was this weight that lifted off of my shoulders because I felt, “Wow. Okay. I can go back to creating. I can go back to doing the stuff I know how to do,” part of the journey is knowing when something isn't your strong suit. And I feel like that should come as a relief, not as a disappointment. So find the smart people who know better than you and ask them for help.


SS: And last question, are there any books that have been particularly helpful for you or impactful on you as you set out on your own to build your independent career over the last few years?

TT: I think a lot of the standard books that really have been helpful, that a lot of us read, definitely Think and Grow Rich. I would definitely say Rich Dad, Poor Dad. Those books have definitely been helpful for me about thinking beyond, thinking about thinking with a greater mind and thinking with a different mindset too. I haven't picked up anything recently, but I definitely am more into right now affirmations. Not necessarily an affirmation book, but I have a set of affirmation cards by Louise Hay that I have been using lately. And I journal just looking at those prompts and those sayings, but there aren't really any books that I'm reading currently because I've been doing so much reading and writing for my own research that I haven't had the time to read for joy or pleasure. And that's something I definitely want to get back into as we are delving into the new year.


SS: Awesome. Well, I'm going to look up the affirmation cards for sure. So Tasheen, that is it for today. This has just really been a pleasure. I'm so grateful that you took the time to share your story and all of the really, really great advice that you did share with the readers and listeners. So thank you so much for joining.

TT: Thank you for having me, Shelby. I greatly appreciate the opportunity.