Judith started her blog when she was well in her 60s as a way to cope with her husband’s disease. Now 8 hears later it has turned into a business and a career as a model.

These are the highlights of my interview with her. The interview has been edited at places in its written form to make reading easier and more enjoyable. If you prefer to listen, you can go here.

How to turn your hobby into a business – an interview with Judith Boyd

Sylvia: When did you start the book and why?

I started my blog in July of 2010 and I was influenced and inspired by Ari Seth Cohen’s Advanced Style blog which gave me the courage to start.

Also my husband was encouraging me to start. He was my photographer and he was also dying of cancer at the time. He’d been sick for about five and a half years and it was during the last nine months of his life that I blogged about cancer care, caregiving and outfits. I would dress up and go with him to chemo and in the exam room prior to his infusion, as we waited, he would take photos of me.

It was like a “What to wear to chemo” series. I posted other outfits as well. In fact, in the beginning I posted more frequently but I didn’t write as much. That’s how my blog began.

I had no idea what I was doing and I just kind of launched into the abyss and blog through to the end of his life, death and then grief. Since it was a project that we started together, I just kept on going because I feel like he offered the gift of a lifeline to me.

Sylvia: I stumbled upon your blog just before your husband passed away. It was so moving. It was so sad. I was really drawn to both your outfits but also your writing. You could write so beautifully about your experiences and about this difficult period and it was actually quite moving to also see how you then recovered from this period.

For now, let’s go back to the beginning. How did you find readers for your blog?

I think one of the things that helped was that my daughter was living in New York City at that time when I started and I went to visit her in New York. I had gotten to know Debra Rappoport who lives in New York through the blog, and I arranged to have lunch with her. To my surprise she brought with her Ari Seth Cohen from Advanced Style and he featured me on the blog.

From then on every time I visited New York, he featured me again, so that gave me more followers. What he was doing was revolutionary and he provided visuals for all of us that are 60 and over and even any age really, that we don’t need to fear aging.

That there’s so many benefits to it and that we can continue to dress up and have a good time. So I would say that Ari did support me in many ways and also I found in the process of blogging other such supporters like you, Sylvia.  Other women and some men were blogging about style and so began interacting with them too. Then later on, I think was about three years ago. I started instagram. That has really blossomed for me, so I’m very grateful for all of that.

Sylvia: I think in the beginning you did actually also comment quite a lot on other blogs, right? You could really see that there was a little bit of a community blossoming. All these things can really help, but definitely your connection with Ari Seth Cohen helped you as well. He also featured you in his book, did he not?

Yes. In both of his books I was honored to be featured. have met some of the women and men that I met online during that time. It’s very much a community and a support system that I didn’t know existed and it would not have been there if I hadn’t started blogging.

Sylvia: That’s a good point, because like you mentioned, you started your blog for yourself, right? You wanted an nice hobby, to be supportive and be supported and connected with other women, and then before you know it, it turns into something else.

Yes I really didn’t know that that was going to happen. I didn’t know that there was a community that was so kind and generous.

I think the message is to just start something even if you don’t know what you’re doing and then learn along the way. If you’re determined and passionate and consistent, you don’t know what’s going to happen. I would have had no idea that everything that has happened could have happened. It was a total gift to me then and now in my life.

Sylvia: And so what happened after you started to get more readers. When did your hobby turned into a little bit of a business?

I think that I started making a transition about a year ago.

There were difficulties about it because I started my blog as a way to develop, as it turned out, community and relationships and so to become a business at first felt uncomfortable. But as we’ve talked about before, if you don’t feel uncomfortable, how do you grow? So I just stuck with it and started very slowly and there were other bloggers like you Sylvia, that have always been a role model for me in this area.

Now that I’m starting to transition to a business I feel the energy growing,

Sylvia: the energy growing for your blog or for yourself?

The energy of the business and the energy of myself that I’m becoming more accustomed to having made this transition. There’s so many role models out there. It’s very helpful to see other people do it as well.  I guess it has something to do with changing from a personal blog that I had developed relationships with and then how I saw myself when I transitioned to a business. Does that make any sense? It’s kind of how I viewed myself.

Yes. I also hear from many women that they find it difficult or feel conflicted about selling to people or monetizing a blog and that they feel that it is not right. Those feelings are very common.

I did and I still do some times. Yes.

What helped you overcome them?

Talking with other bloggers that were monetizing helped. I have relationships with other bloggers and instagrammers that have made this transition, which I find very supportive. We email and ncourage one another. That same support system that I developed during the time that my blog was so personal,  is now helping me to find support from others who are doing the same thing in terms of monetizing. That’s one of the reasons why I’m feeling more comfortable as time goes on.

Do you feel that it is more empowering to now earn a little bit of money on the side from your endeavors as a blogger?

I think that we all have issues about what is financial abundance and what my self talk includes. That financial abundance is just another form of energy. I’m dealing with my own issues about what that means and to see money as a form of energy and that it’s okay for me to embrace that as well as embracing other positive forms of energy. That’s the thought process that I find myself relying on.

Yes. I often tell other women that if you have gifts, it’s almost your obligation to share them. Right? If you don’t sell them, how can you share them? How can other people really appreciate that? I think it’s often very important to monetize some of what you do because you will value your work more and other people will value your work better.

It’s a lot of work to blog and I think it’s only fair that you get compensated for a lot of the effort that you put in.  For example, your images have gotten better and better over the years and I’m sure it takes you a lot of effort to produce such good images.

Right? It really does. There’s a huge process. Choosing an ensemble, making sure that it reflects what I want to project and  I do my own makeup and do my own styling.

Then there is the photography that takes time and then there’s the editing and then the blog. There’s also writing. I found over the years that sometimes it feels like a full time job.

Therefore if I’m doing a full time job and it’s not providing some kind of financial abundance along with everything else or that I’m creating, there comes a point where I will ask myself: Am I going to continue to do this?

Exactly. You did start something that you really enjoy and that in the beginning is very important. But at some point you need to monetize. So tell me, what steps did you take? How did you start to monetize your blog and your instagram?

One of the things that started to happen is that I would get emails from brands that asked if they could provide compensation for me to feature them and that still happens. I never know what’s coming in my email, but also I now have someone working with me part time to reach out to brands here in Denver.

That’s a very good point you’re making because a lot of bloggers always think, oh, I have to wait for someone to call me! But actually you can do quite a lot yourself  by reaching out.

Well, yes. Some of the businesses had no idea and had never seen what I do. If they hadn’t been approached, they hadn’t thought of it. I’m very, very selective as to who I want to represent. The brand needs to match my aesthetic. I wouldn’t wear something that I didn’t feel comfortable or didn’t love. . It’s the same as what I have been doing all along, that I need to be passionate about what I am wearing and what I am writing.

I think that is so important because it’s so important to stay true to yourself. Right? Otherwise people will see, oh, she’s just doing that because she gets compensated. But if you stay true to yourself, then there’s no harm whatsoever to monetize what you do. I think it can actually be a lot of fun because in your case, you get to do all these really fun model shoots. Right? I’ve seen some really wonderful photos come by and and I think makeup gets done for you. You get dressed in really beautiful clothes and sometimes go to a fabulous locations!

Yes, yes, and I’m learning so many new things, but I think the point of remaining authentic is so important because my followers would be able to tell that I was not remaining true to myself and I would be able to tell, which is the most important.

The other thing that is happening is that I’m meeting new people who are creative and so I’m developing new relationships that I didn’t have before because of this. Collaborations bring about new friendships,

is it just modeling that you do? You also do some affiliate marketing now on instagram and on the blog, is that right?

I’m starting to do some on the blog. I haven’t really. The plans are all in place and it’s going to happen, but I really haven’t started that yet.

The thing that I’m starting to do is speak.  was approached by a woman who is teaching widows to become widowed coaches. I’m not going to go through the training of becoming a widow coach because what I’m doing now takes so much time, but this is something I’m very attracted to.

What I want to do is provide a presentation for either widow coaching. It’s just in the very beginning stages and i’m also thinking of a program. I’m going to put together a powerpoint and talk about two other women who are now widows and talk about the process that worked for me or that I experienced.

Everyone is different in how they grieve so it would be a combination of what I have learned from blogging and using my mental health background. This just seems like a dream and for me, I’m 75, so when am I going to do this, wait until I’m 80?

So I feel a sense of urgency to do the things that I really love to do and want to do and give back as well as move forward in monetization.

I’m so thrilled to hear that you’re creating a programme and doing this meaningful work! I always recommend bloggers to create something. Yes, you can monetize with affiliate marketing and advertising and modeling, but nothing is more powerful than to create your own products. 

Especially because a lot of women, especially older women,  have gained so much knowledge about so many things and like you said, you worked in the mental health space. You’ve experienced what it’s like to grief. You came out the other side really full of life and ready to take on the world. You have so much to teach others and so many gifts to share and I think that other women, other men, a lot of people would really benefit from your teaching and help, so I’m thrilled to hear that you’re going to do it.

Thank you. I’m excited about it. Just starting. I had the idea and am now operationalizing it. Those are two different things and there’s steps to go through and at the same time I want to continue doing what I’m doing. It’s going to be fun and I’ll be very excited when I start doing it. There’s so many people that are turning 60 now every day and with aging comes loss. It’s just part of the process and I want to be useful in that area.

Yes, I think it’s going to be very, very powerful. So were there ever moments in your blogging and your business creation that you found it too difficult or that you were thinking of quitting?

Oh yes. I think it just comes with the territory. I started blogging before Nelson left my life and I was still working part time until just about a month before he died. It was only about one day a week, but still I was in the healthcare industry. I didn’t have a period of time where I stopped something and contemplated what to do. I went from my passion for healthcare to blogging and that took up so much time that I’ve never really had that period of time where I contemplated what am I going to do with my life. It was there. I was driven about it.

There have been many times that I thought about quitting and I think that’s normal, because it does take a lot of time and I think, well what would I be doing if I wasn’t doing this? How would my life look?

It’s hard for me to even take a a social media break because I’m so excited about instagram and that I would miss out on something but I know it would probably be healthy for me to do so.

But there have been times when I have felt overwhelmed and thought of quitting because I was spending so much time on it. Now that I’ve decided to monetize this hobby I have come to a crossroad. Am I going to continue to do this as a personal passion or am I going to take the path of developing a way to be compensated?

I also thought of quitting after Nelson left. I, I thought of it at different points along the way. But it’s always been short lived. What got me though these moment is just the pure joy of doing it. That’s the good thing about having a fashion blog. There’s always something to write about.

It’s interesting because I started in July of 2010 and I was blogging more regularly in terms of frequency at the beginning. Now I blog once a week and I instagram probably about four times a week.

If you had to make a choice, would you quit instagram or the blog? What’s more important?

It’s really hard to say because I really enjoy writing and thank you so much for your kind words about my writing. Prior to my blog I wrote in the medical arena, but I worked in mental health so it’s really comfortable because I would write about feelings, how patients were presenting and so on and so I just turned that around and talked about how I was feeling.

I love writing and it’s like a muscle that you develop over time and I don’t want to give that up, but instagram, as you know, I’m a lover of headwear and I have found so many milliners across the world. I wouldn’t have known they existed without my instagram, so everywhere I travel there’s either a blogger or an instagrammer or a milliner that I visit while I’m there. It opens up the world! So instagram is different than my blog, I guess I have to say that they’re equally compelling for me.

What would you say to other women that are thinking about doing something on the online space?

If you have an idea in mind and whether it’d be a blog or instagram, the only way to find out whether or not you like it, is to just do it. One of the things I did before I started my blog, is to take a class on blogging, which was helpful, but it’s totally different because it’s cognitive and it doesn’t involve the actual putting yourself out there on a blog or instagram, but just give it a try.

And I don’t think you have to know everything about it before you do.  I I learn by doing. When I started my instagram, I had no idea what I was doing just like with my blog. But by doing its practice, you get better at it. As time goes on, you’ll find the people that you are drawn to and it can be very exciting. If you have an idea and feel some creativity about it, what’s the worst that can happen if you try?

Exactly! That’s what I always recommend. There can be lots of benefits in learning and I have a workshop that you can do for free online, but in the end you only learn from doing and I always encourage people just to start because you learn so much from your mistakes and will learn works. 

And I didn’t have your classes when I started. If I would have. I think that’s a real benefit for people to take a class from you. Sylvia,

well, I’m still developing mine, but there’s a few free resources that I’m already offering and then in the future I will definitely provide more classes. Especially because I see that a lot of bloggers who do not know how to monetize or they’re monetizing the wrong way. I think what you are going to do is going to be so powerful, so I really hope that you continue to do that and create those presentations and record them and put them online. I think that will be a great resource for people to have.

Thank you. And the other thing I started was a youtube channel for a while. I was doing it every week. Now I’m so busy that I’ve slowed down, but I’ll restart again. It’s another area of challenging myself.

I didn’t even know that. You have to publicize that a bit more on instagram to let people know that you’re doing that!

I will when I think that I have enough to give it a start and I feel like I’m better at it than I am right now, but even talking with you today helps me in that endeavor because written communication is so different than oral communication and so it’s something that I’m working on right now.

I’m learning too. I mean that’s why I’m doing this new podcast. Right? I want to get better at speaking. I want to get better at interviewing. It’s a process and it’s challenging for sure. I’m very comfortable blogging, not so comfortable speaking, but you only get better as you start doing it!

Finally, Judith, how do you see your business develop in the future? You already talked a little bit about your plans for your course. Anything else that you want to share?

Well, I’m working on video, so that’s a new challenge and I’m going to be practicing that. I still don’t have the affiliate links up on my blog and then the powerpoint around widow coaching. That’s something I hope to put in place in the near future. I also want to continue to improve with photography because that’s such a big part of blogging.

Everything that I’m doing now I want to improve at and then I’m adding video and presentations. I think it’s good to have multiple sources of monetization.

Yes it is definitely good to be on several different platforms, but you do have to be careful. That can take quite a lot of time and you do need to really focus your time on one thing in the beginning. Once you’ve built momentum there, you can move onto the next one.

It sounds like you have lots of plants. I just love the fact that you’re always so driven. Some of my friends say Sylvia, I don’t know any other women that are as driven like you and that really want to constantly learn.

But I do know them and you’re definitely one of them and you will never stop. Which I really, really love. I love how you embrace technology and learning and stepping out of your comfort zone. You are definitely a great role model for many women, so thank you so much, Judith, for being on my podcast.

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