How To Stay Positive And Ignite Positive Change On Your Entrepreneurial Journey

How To Stay Positive And Ignite Positive Change On Your Entrepreneurial Journey

What you seek is what you get, Dorothy Illson believes. You can take this piece of valuable advice any day from the founder of Needle’s Eye Media and host of Do Well & Do Good podcast.


Not only has Dorothy, a seasoned digital marketing expert, invested copious amounts of time, effort, and dollars for her clients, helping them scale their businesses, but she also hosts a podcast for purpose-driven entrepreneurs like you. It’s all about the stories of people who have not only created personal and professional success but who leveraged their success to help create positive change.

The truth is continuous personal development and mindset walk graciously alongside financial goals on the entrepreneurial journey towards fulfillment.

If you’re ready to create the life you want, watch the video interview below where James Swanwick interviews Dorothy Illson. They dive into tips for a successful career shift, and how to stay positive, achieve financial freedom, and increase a positive impact in the world.

We know you have the power in you to ignite incredible change. Now, all you have to do is reach for it.



Connect with Dorothy:


Key topics and timestamps:

01:01 - Introduction

03:49 - Overcoming obstacles with a positive mindset

12:25 - A day in the life of Dorothy

16: 17 - Self-awareness and hypnotherapy for better sleep

18:20 - Resistance may be the answer

20:18 - The importance of feeling you’re making progress

26:07 - Productivity tips

30:07 - More about Needles Eye Media


Full audio transcript:

Download transcript

James Swanwick: Welcome to another show. I am James Swanwick, founder of Swanwick and the James Swanwick Show podcast and the alcohol-free lifestyle podcast, amongst other things, and today we're talking about how to stay positive and create positive change. And I am joined by Miss Dorothy Illson. How are you, Dorothy?

Dorothy Illson: I'm good. How are you, James?

James Swanwick: I'm doing so well. Thank you for being here. Dorothy is the founder of Needle’s Eye Media, which is a full-service digital marketing agency, and she's also a fellow podcast, so she hosts Do Well & Do Good. And, you're based in Chicago, right, Dorothy? Tell us a little bit about your life and who you are and what you do and maybe just wrap that up in what is feeling good and staying positive means to you. How important is that? I know it's stating the obvious but like, just, what is your viewpoint or how you live your life to stay positive.

Dorothy Illson: Yeah, absolutely. So we'll kind of start with today and then I'll take it backward. So, as you mentioned, I do run a digital marketing agency specifically we do Facebook, Instagram, and Google paid traffic primarily for digital product businesses. Businesses that are really looking to scale their customer acquisition with paid traffic. So I got here in a very roundabout way, I actually went all the way through school with a very kind of stereotypical idea of what a successful career would look like. Love the Swannies you just put on by the way.

James Swanwick: Look at the Swannies here for anyone who's listening. I just put on a pair of a little bit of a fashion show as we're doing this, Dorothy.

Dorothy Illson: Well, you know when I had you on Do Well & Do Good a long time ago, you were kind enough to send me a pair of Swannies which I never get to wear because my fiance Jacob commandeered them about two days after they arrived, and he wears them constantly. So, anyway, like I said, had just a very kind of traditional view of what a successful career was going to look like. And so that kind of got me on the path of finance and accounting. And long story short, we can dive as far into this as you want definitely a lot of positive mindset stuff that comes with it. But two weeks after I graduated, I ended up giving up the accounting job that I'd worked so hard to get, and went to go work for a startup instead. And that was really because I had,  as cliche as it sounds, discovered personal development, and it really took me down a radically different path. I worked at a startup here in Chicago for about three years after I graduated, and then started the agency and now I'm blessed to work with some really incredible business owners, in helping to scale their paid traffic. So, in terms of a positive mindset, staying positive, I think we could dive into so many different areas, you know, I would say the common thread along every single part of my journey has been relying on the strength of my mindset to push through obstacles and to ultimately continue along the path towards what I really wanted. And so that's certainly not to say that I am perfect at this. I think for all of us, it is a constant daily work in progress. But it is something that I believe is the number one key to achieving, really anything that you're looking to go after.

James Swanwick: There's a book named a beautiful constraint. I'm not sure if you've heard of it by Adam Morgan and Mark Barton. And the book in a nutshell really talks about overcoming obstacles or going around obstacles and the mindset that is required for that. You know, every cloud has a silver lining, when life gives you lemons, you make lemonade constraints, you know are assumed to be a bad thing, but in reality, they can often be the thing that creates momentum and creates breakthrough. So, how have you, where has that shown up in your experience as an entrepreneur and as a wife, or maybe as you know, just in your life and your health where you've seen an obstacle and rather than even going around or over it, you've actually changed the goal like even made a bigger goal because there's a way where you can overcome an obstacle to reaching a goal. But then there's another process where you can actually just do what, oh, this challenge we've got here is helping me create an even bigger, bigger goal.

Dorothy Illson: So, I'll take you back to you know, after I had worked at this startup after graduating and, basically the co-founder of that business who was really the reason I'd been there so long, he ended up leaving and so I knew I wanted to leave too. And, as I was kind of looking around at other jobs, I knew I didn't want something corporate, I wanted somewhere that I would have the same level of flexibility that I'd enjoyed in my last job. So, I could work remotely when I wanted to. I had a lot of autonomy. And as I started kind of interviewing places, I realized that it was going to be very difficult, potentially, for me to find that again. And so I got this idea in my head. You mentioned you found a challenge and you ultimately started to dream bigger. I thought, well, what if I tried to do something on my own, and that was a scary thought, but it was an exciting thought at the same time. And so, basically, I went off on my own. I kind of thought well, worst-case scenario, if this doesn't work out, I'll go get a job. And hopefully, we won't come to that. But after a few months, I was really floundering. I didn't know what I was going to do, I had made absolutely no money, I was renting out my apartment on Airbnb to pay the rent. And I was really close to reaching my breaking point of having to kind of give up on this dream I'd created. And it was really a function of working even harder on my mindset than I was on trying to figure out a business right? And as soon as I really focused on that, you start to see opportunities, where they didn't exist before. So basically what happened for me was my old boss, he had a ticket to a workshop with, really an incredible Facebook marketer named Jason Hornung, and he couldn't go so he offered me this ticket. And I've been involved in our paid traffic at that startup, but you starting an agency was really kind of not an idea on my radar. But I went to this workshop. And there, Jason was basically pitching this, $30,000 year-long coaching program for people building an agency. Now, I was not building an agency at that time, I didn't have $30,000 I didn't really have $1,000. But I believed in my ability to figure things out. And I believed in my ability to take each challenge as it came. And tackle it with that mindset that I mentioned, and so, I ended up putting that first payment for Jason's program on a credit card and just left without a parachute. And so, I think that experience really taught me a lot. You actually had kind of a similar experience with Tai Lopez and joining his program. And what I found was that putting my back against the wall, and then like I said, working on a positive mindset equally as hard as I was working on the business, within just a few months, I made back all the money I needed to pay for Jason and was kind of off and running, building the business. So, I think it was just a lesson for me that, when we don't have certainty in the path, we can have certainty in ourselves. And that's really all that it takes in most situations.

James Swanwick: Yeah, well said. I like that. If we don't have certainty in the path, we can have certainty in ourselves. Similar to when I first invested in as you mentioned with Tai Lopez coaching back in 2013, I transferred 25,000 American dollars which is 32,000 Australian dollars from my strain bank account into his bank of America account on October 31, 2013. And, as we're recording this now and 2020, 7 years later, generated millions of dollars in revenue. My products have helped change many people's lives, obviously through quitting drinking and the Swannies blue light blocking glasses helping people sleep better. I remember I had my father over actually just last night for dinner. And I remember seven years ago when I told him that I was sending Tai Lopez $25,000. He said you're doing what? Who is this? Who is this Tai Lopez, person? You're 25 and I want you to, like, he was shocked. And that was funny because I had him over for dinner last night and I was sure that investment worked out. Okay. I think you know.

Dorothy Illson: I didn't tell my parents. You had more guts than me.

James Swanwick: But it's true, isn't it? I mean, even now I'm still going through that, again, like in the sense that I really want to build another brand. And there's a gentleman, Ryan Daniel Moran, who wrote a fabulous book called 12 Months to a Million Dollars. It's been a friend of mine for a number of years. And he has a paid program that's coming up on how to build a brand and getting it ready for exit. And I've friends with him. And part of me is like ego kicks in and it's kind of like, I'm experienced enough now that I shouldn't have to pay for coaching. I should just like, I'm feeling a little bit embarrassed to actually even say to someone that I've known for seven years and who have built businesses with, actually, can you help me? So that's so funny how the ego kicks in even as we move along, even after having success in business and things like that. For me, at least, my ego still gets in the way. I'm doing it. I'm enrolling in it and I'm coughing up the cash to do it, even though quite frankly,  I don't need to. I'll do it, it might just take me a decade. Whereas if I do it this way with him, and I pay for it, then I'm going to pay attention. And I might do it in like two years. So I think that's the same with anything when you have a coach or a mentor, and you put your back up against the wall, and some people may use the phrase, when you burn the ships. You give yourself no retreat, that's when you actually focus and get things done.

Dorothy Illson: Yeah, you know, I really couldn't agree more.  I think you look at all of the free education that's out there. That we typically just don't take advantage of the reality is that when you have skin in the game, when you pay for something, especially when you pay that amount of money for something it's definitely something that's gonna light that fire under your ass to make things happen. So, I think you really put it perfectly that it's not that you can't get to the same goal without help. It's that you're going to do it. So much faster. So that's really, you know, keep.

James Swanwick: You're buying speed actually, you're investing.

Tell us a little bit about how you manage your time and your productivity. I'd love to know a day in the life of Dorothy actually, like what time do you wake up? What do you do when you spend your day? What's your nighttime routine? Walk us through that.

Dorothy Illson: Yeah, so part of the reason that I allowed Jacob to steal my Swannies is that he has a lot of trouble sleeping and I have always been very skilled at sleeping. It's funny like I would say that the one piece of my routine that I absolutely never skip is getting at least eight hours of sleep, usually nine. I'm someone who just knows that I function the best when I am well-rested.  I hardly ever drink as you say is such a huge part of Sleep. And so, I get a good night's sleep, I wake up, usually at about 7 am. And then I like to move my body first thing so usually either a walk or a run or if I'm doing a workout I'll do that. Hydrate, before that I have celery juice every single morning. And then when I'm done with whatever kind of movement I'm doing that day, then I meditate and I journal. I think for me, it's the journaling piece that has been kind of the foundation of my positivity practice, if you will. It's definitely the one thing where if I feel like I am kind of in a rut or I haven't been moving forward, things aren't going well. I can just always open up my journal and see, okay, I haven't done this for two weeks,  let's get that back on track. So it's something that just has a dramatic impact on me. So that's kind of my morning routine then I usually check in on slack with my team to see how all of our ad accounts are doing that day and what's going on with all of my clients and then the rest of my day is usually filled with calls with my clients. Some strategy sessions with my team and really just making sure that we are executing for everyone that we work with at the highest level possible. And then I usually wrap up the day around six, seven o'clock and cook dinner and enjoy a quiet evening, go to bed early.

James Swanwick: What time is early for you?

Dorothy Illson: Um, honestly, I usually get in bed about 9:30 and I'll read for a little bit and then go to sleep around 10 and wake up at seven so I get my nine out.

James Swanwick: Yeah, I've been experimenting with waking up early and going to bed a lot earlier, so as early as 7:30 or 8 and trying to get up around I mean, this week I got up the hill so get up at 5:30 but I'm trying to see if I can get up at five. Trying to train myself to get up at five. Because I'm in Australia at the moment with COVID-19 as we're recording this, and I'm most of my businesses are in America. As soon as I wake up I'm on, because in America it is already lunchtime there. And what I found for a couple of months during COVID-19 lockdowns was that my daily routine of writing in my gratitude diary and exercising and doing like 10 or 15 minutes of meditation and just being intentional and writing and my vision for the future and stuff was that getting pushed to the side because I was waking up and straight away I got calls and podcasts, interviews and meetings and things like that. So I've been there just this week actually, I've been intentionally attempting to go to fall asleep sooner and wake up earlier and make sure that I don't compromise that kind of morning routine. Any thoughts on that?

Dorothy Illson: Yeah, you know, it's interesting. I think self-awareness is so huge and absolutely everything. And so for me, I actually work with a hypnotherapist, and that has been life-changing. And that's a whole other rabbit hole that we can go down if you want. But, it was interesting. I was in a period where I was trying to do the same thing as you, I was saying, okay, I'm going to be a real entrepreneur or a good entrepreneur, I gotta be getting up early, right? That's what they all say. So I was trying to get myself to wake up at 5:30, 5:45  and it wasn't going well. Let's say that. And so in a conversation with my hypnotherapist. I was talking about this, and he was having me kind of describe my morning and my thought process. And what he realized was that every morning while I was waking up, the very first thing I was doing was beating myself up for snoozing my alarm till 6:15 or, for not jumping out of bed at 5:30. And he kind of pointed this out to me like, so you're starting every single day, attacking yourself and talking down on yourself, for meeting this or not meeting this arbitrary standard that you set. So why don't you just decide that you have permission to wait, go to sleep at 10 and wake up at seven? And that can be okay. Right. And so, I think for me, what I found was, that schedule really worked for me, and so I think there's so much power in just being self-aware. So like for you being Australia like you said, you need that extra time in the morning to be able to kind of get into things like for me, it's okay if I start work at, 10 am because that's what works for me and my schedule. So it's all very individual I think.

James Swanwick: Yeah. I found that when I do, I wouldn't say it's a love-hate relationship with meditation. I would say I love meditation. It's just I hate starting it. I hate beginning it. So when I'm doing it, I love it. But the actual process of sitting down and just going closing my eyes and beginning, Oh, I have so much resistance all the time. And this is you're talking to someone who's done a 10-day silent meditation, you have a passion or like I've done all that stuff. Anything that you have resistance to, anything that you have a lot of resistance to, that so damn good for you. But Dorothy's mind is just like, not today, I don't want to do it.\

Dorothy Illson: It's interesting. I mean, definitely, it's kind of the same answer. It's the meditation and the journaling, which is so funny because it is, without question, the thing that keeps me you know, on the right track, in terms of my mindset and my thinking patterns, and it's not something that takes a lot of time. I mean, I certainly have more than half an hour in the day that I'm just wasting on, stupid stuff, whatever social media. And so the fact that we can be so resistant to taking that time to do something that has a dramatic impact on our mental health and well being is pretty shocking. So, I think that, for me, it's traveling where things really go off the rails. So, you know, obviously, 2020 hasn't been as much traveling my calendar. So it's really been a time where I've focused on solidifying my routine in a really powerful way. Because I think when you turn it into something that is as routine as brushing your teeth, it becomes harder to ignore it and then let it go.

James Swanwick: Yeah, it's amazing how the human brain as well, I'm not sure if you find this, but when we first discover something new, we just did, we fall in love with it, right? And we want to tell everyone about it. Like, ah, because this new book, you've got to read it. It's incredible. It was like, Oh, I found this new thing. And I'm doing this. It's incredible. Oh, guess what I'm doing stretching. I'm doing meditation. It's been a game-changer. And you hear this all the time. And I've been guilty of this all the time. You go charging over the hill, a million miles an hour and then two, three weeks into it, you start the slippery slope, start to get you and then week four or five, you're in the drift and then week six or seven is like what was that thing I was doing again? And then you have to keep reminding yourself of coming back. So it's funny because I'm not that self-disciplined. I mean, I'm self-disciplined in many things, but I'm not self-disciplined in other things. But what I have surrendered to I guess is as long as I'm making progress, even if I'm not always consistent, as long as I feel like, I'm making progress, I'm okay with that. And I used to beat myself up about it all the time. Like I should be doing better, I should be doing meditation, I should be making more money, I should be selling more things. And then I have to come back to like Jordan Peterson, the famous Canadian Psychologist talks about it in his book 12 rules for life and he says you always just got to compare yourself to you and your progress. And that makes me feel somewhat better when I wake up sometimes in the morning and I'm beating myself up. 

Dorothy Illson: I think it's perspective, right? So you mentioned how important it is to feel like you're making progress. I read a book several years ago, called Zen And The Art of Happiness by Chris Prentiss. And it's a short book, a simple book. But basically, it encourages you to operate under the premise that everything that happens to me is the best possible thing that could happen to me and it's really interesting. I think all of us if you look at events in your life, every single person listening to this, you can probably point to at least one thing that has happened to you that at the time felt devastating, it felt like, unequivocal, negative event, this is a bad thing that happened. And then in hindsight, you realize that it was actually to your benefit. It led to something better, whatever it was, whether it was you know, breakup, or losing a job. And I had an experience like this when I was in Jason's coaching program. I was in the very early days of building the agency, I was getting some traction, but it was still a major grind. And my old boss came to me with an opportunity to work with him in the new company that he had gotten involved in and so this was a job in essence. They were like, you can have some clients on the side, but this was almost a full-time gig. And I jumped in, I thought, Oh, this is great. This is going to be stability and I can still whatever, I made all kinds of excuses for why it was the right move. And then about, a month, six weeks later, I lost the opportunity. They realized that the business was so early on, like, there were kind of too many cooks in the kitchen. And really my skills just overlapped 100% with that one of the co-founders. And so, I basically, you know, I lost that gig, and at the time, it felt devastating, it felt like you know,  this was going to be an amazing opportunity for all of these reasons. And I was, really in a position where I had to choose to look at this as an opportunity. And even though at the time it felt so negative, losing something that was really kicking out the crutch that I was leaning on to avoid actually building this business. And being on my own. And so, in hindsight, looking back, thank goodness, that the bad opportunity fell out from under me because if it hadn't, I never would have gotten to where I am now. And where I'm continuing to go, building this business of providing other people jobs of, you know, getting results for my clients and really building something that I'm proud of and that I'm excited about. And so now, I really try to look at everything that happens in that light. How could this be the best thing that could happen to me? And when you start to ask yourself that question, your brain is going to search for answers. And so even in the darkest moments, the scariest situations, you can start to look for the opportunities and looking is certainly the first step to finding them. So that's been really powerful for me.

James Swanwick: Yeah, Tony Robbins says if you want better results ask yourself better questions. That seems like you want master results. Ask yourself master questions. It's powerful stuff. I want to geek out on some productivity tech stuff. What do you use? I think you use Asana right. To put things in. Tell us a little bit about how you plan out your day like for the entrepreneurs or the productivity geeks out there listening. What kind of to-do lists do you have? How do you get things done? What tech are you using?

Dorothy Illson: My whole life lives in Asana. So, for a while, I would just have kind of work tasks in there. But what I found is that when I started to use Asana to track everything that I needed to do, like schedule a dentist appointment, it takes this mental burden off you. So all of these things that you just have in your head like, I got to do XYZ, I have to literally have a task in Asana twice a week for you to call my grandmother. And it sounds kind of silly, but it is very freeing, at least for me, to know that I can just go into Asana every day. I break things out, what I've got to do today, tomorrow, this week, next week. And whenever I realize that like, okay, I've got to schedule a dentist appointment in six months, I put it in Asana to mark that due date in six months. And I know that it's going to pop up on my to-do list when it needs to happen. And I don't have to worry about it. And so that has been very powerful for me. And I think one of the keys to productivity and staying positive for me is being realistic about what I can get done in a day. Because I think for a long time, especially when I first started the business, and especially when I was working alone and didn't have a team. I was just completely unrealistic about what I was, assigning myself for any given day. And so inevitably, every single night I would have to shut down, Dude, are you leaving things undone? And so again, just like not being able to wake up, jump out of bed at 530 in the morning. I was beating myself up at the end of every single workday, and it wasn't because I was not being productive or not working hard, it was because I was trying to fit three days worth of work into every single day. And so just being more realistic about what can happen and then planning that,  I'm able to work my way through my tasks for the day, and then maybe I get to get started on one of my tasks for tomorrow. And that leads to a much more positive empowering mindset around work and productivity than the opposite. 

James Swanwick: Yeah. Tony Robbins, again, to quote him says that we overestimate what we can achieve in a day and underestimate what we can achieve in a year, for example, or you could just change it to a month as well.

Dorothy Illson: I've heard it, one year and five years. I think it's the true kind of how you shake it. 

James Swanwick: It's amazing. Like, I'll sit out at the beginning of a week and think this is what I'm going to do this week. And no matter what, I'm going to get that done and then all of a sudden stuff comes up. And I'm like, oh, I've got to do that. I want to do that. That's good. Oh, yeah, go do that. I'm going to add that to this and before you know, it's like these hundred different things on there. But I am chasing the shiny new rabbit kind of guy. Like trying to chase it. I actually do like chasing shiny new rabbits. It's just, I haven't quite yet fully mastered the sequence with which I chase them. Because I think if I can master the sequence, then things will be a lot easier. And unlike you, probably wouldn't beat myself up so much for not seemingly getting things done.

James Swanwick: We're talking about Needle’s Eye Media as well. I'd love to know a little bit more about that. Can you tell us a little bit more about that, Dorothy?

Dorothy Illson: So, what we do is, about 75% of our clients are selling digital products or services. So we work with a lot of personal brands, a lot of companies promoting things like your 30-day out no alcohol challenge, products like that. And our ideal client is someone who is spending between 10 to $40,000 a month on paid traffic and is looking to scale to 100,000- $200,000 a month. And you mentioned my podcast is called Do well and Do good. And giving back is something that's really important to me. And so I really make it a priority to only work with businesses who I do feel are really doing something good in the world and that really makes my world a lot more fulfilling. I believe that paid traffic is really the best way to create leverage in your business and really be able to kind of turn on the faucet when you're ready to really pour it on and scale your customer acquisition in a predictable way. And so that's really what we help our clients to do.

James Swanwick: Yeah, you can check out more on, which is Dorothy's full-service digital marketing agency. You mentioned before, I think I might have referred to you as a wife, but it's your fiance. Is that right?

Dorothy Illson: Yes, yes. No worries.

James Swanwick: So I stand corrected. I'm sorry. I've got ahead of myself. I'm sure your fiance's keen for you to be his wife. 

Dorothy Illson: He's gonna have to wait a little longer now, thanks to our friend Coronavirus.

James Swanwick: Is that right? What's happened?

Dorothy Illson: Well, we were supposed to get married on September 19. And we ended up moving it to October 2021. Just so that we could be at least more confident that we can kind of have the celebration that we wanted to have. So honestly, it was stressful before we moved in. Now that it's done, I'm just glad we don't have to stress about it anymore.

James Swanwick: Yeah, you know, there you go,  without actually even reading the book that I referenced before, like a beautiful constraint by Adam Morgan and Mark Bird and you've already changed the goal and you've already overcome the obstacle. So that's great.

Dorothy Illson: Well played. Thank you. Thank you. It's funny now though, because of everyone moving their 2020 weddings to 2021. I'm gonna have seven next year. One is the maid of honor, one as the bridesmaid, and one is the bride.

James Swanwick: Oh, wow. That's true. Because when all this dies down COVID-19 is going to be a flurry of weddings out there. 

Dorothy Illson: My sister was very gracious letting us move our wedding to three weeks after her.

James Swanwick: Well, Dorothy, thank you so much for sharing your expertise with us today. I love the topic of staying positive and productivity and mindset and overcoming obstacles. And yeah, it's a testament to you that you've been able to handle all those things, the way that you have. So thank you for your time.

Dorothy Illson: Well, I definitely encourage anyone listening to reach out to me, I'd love to connect with you on Instagram and Facebook. I help you however I can. So James, thank you so much for helping for having me. It's been a lot of fun.

James Swanwick: Yeah, you should wrestle those Swannies back from your fiance as well.

Dorothy Illson: I should. I need to just buy a second pair so I can not rock my own. I want those clear once you got there. So cool.

James Swanwick: Thanks, Dorothy. Take care.

Dorothy Illson: Thank you.


Don’t let your busy schedule prevent you from creating positive change. Click below to listen to this episode on the go.

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Celesté Polley


Celesté is a writer, creative photographer, bookworm, pianist, minimalist, environmentalist at heart, professional napper, and Earth wanderer from South Africa, operating in the wellness industry. She is obsessed with books, plants, the moon, and the misunderstood wild Baboon Spiders (a.k.a Tarantulas) of the arachnid world. Her curious nature has her on an unstoppable journey to work with like-minded humans, but also to help people overcome their health and mental struggles.

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