How To Start A Business In Midlife

how to start a business

Top tips from an expert on how to start a business in midlife.

This is a transcription of my podcast interview with Colleen Kochannek, founder of The Scrappy Frontier community for female entrepreneurs. Check out the audio version of the interview here.

Starting with redundancy

My passion really comes from my own story. I was 48 when I got laid off from the job I loved – along with 10,000 other people. I just knew that at this point I didn’t want to work corporate again.

I didn’t want to sit through like another monthly meeting or do a monthly expense report. I couldn’t do it anymore, even though I’d had a job I loved.

I’d made the decision a while before that I wanted my own business. Quite frankly, I didn’t have the cohones to quit my job and do it. Getting laid off was like a great catalyst for me to get it started. When I got into it, I realized how much I didn’t know about running an online business.

I started taking all these courses on how to start a business and all I found were these really young millennials teaching me and they had no idea where I was coming from. We’re called digital immigrants, meaning we came to technology in our lives, we weren’t born with it. I felt that all these courses started kind of at step number seven.

There was just a huge information gap. Once I figured it out, I thought, I’m going to teach other women how to do this because it’s totally doable and we have so much to bring to the table. That’s kind of what got me started.

It took me a long time to get the tagline, ‘Entrepreneurship school for the typewriter generation’. This also was born out of necessity because Facebook was censoring me for calling people out. Calling women over 50 apparently is naughty language on Facebook, so I had to come up with a new way of describing it. But then it really stuck, cos we did come from the typewriter generation, so I thought it was kind of fun.

how to start a business

Redundancy felt personal because there were 30,000 people keeping their job and I was one of the 10,000 nots.  You take it personal cos you’ve given your whole life to this company and it’s more than a 40 hour a week. You’re traveling, you’re away and it’s time away from your family, etc. so you do give your whole life to it.

Then in a drop of a hat, they’re like, bye-bye. It’s kind of humiliating almost. I was fortunate that I had a bit of a severance package. I had a little bit of security. I had just really made up my mind that I wasn’t going back and I was gonna do whatever it took to not go corporate again.

I didn’t think ageism had anything to do with why I was targeted to get laid off. It was my entire department but I would say this, I saw it, I felt ageism in my job as I started getting older. It’s so subtle and so you don’t see it. People stop asking you specific questions because how could you possibly know about that.

I think ageism is very subtle and insidious and you see them hiring younger and younger people who get promoted faster and faster. These younger people come in at a higher salary than you because you’ve been there 15 years. So you get that annual cost of living increase or whatever but never like a big raise. I think ageism is alive and well, no doubt about it.

Midlife: the perfect time to start a business

In my community, a lot of women just can’t go get jobs again so there’s no option but to learn how to start a business out of necessity. It has become incredibly difficult for us to find new work as early as 40 years old because you’ve just become too experienced and too expensive for companies to hire you or keep you on.

People don’t realize they’re doing it but they do. Paying the bills is a great motivator for starting a business when you need money. Necessity is a great motivator.

I’ve actually written an article about this. It started as 52 Reasons Why Women Over 50 Make The Best Entrepreneurs. It got way beyond 52 reasons. We just bring too much to the table that is almost even hard to pinpoint.

We’ve learned, we’re resilient, we’re persistent, we’re patient, we’ve learned all these things. We don’t need instant gratification. In terms of skills, we have four decades, five decades, six decades. We’ve learned a lot. It’s impossible to not have a lot of skills.

The challenge often is identifying those skills because they’re just a part of us and part of our everyday life. We don’t think of them as skills. We also have skills that a lot of our younger counterparts don’t really have like the whole typewriter thing. It’s funny cos I talk about what the typewriter taught us.

When we had to do something on the typewriter, you had to think that project through from start to finish. You didn’t just sit down and start typing. We had to learn planning skills.

We had to think through the results, the consequence, what was coming next, how do we get from here to there? All of these are great critical thinking skills. Whereas today you sit down at the computer, you’ve got cut, paste, delete, undo, repeat. There’s no having to think through the project.

I worked in education my whole career – higher education and critical thinking is the most lacking skill in our education system today. It’s the number one skill we need in life. The ability to think something through. It’s kind of scary.

The missing link usually is the technology piece and that’s just a skill that can be learned. We have the expertise, we just have to learn the technology piece and you have an amazing entrepreneur.

Colleen Kochannek

Getting to grips with tech

In my group, you’re not allowed to say I’m a tech dummy. You’re not allowed to say I’m tech challenged. One woman calls herself a tech ding-a-ling. I said no, absolutely not.  You’re not allowed to say it. Are you a brain surgeon dummy?

You just haven’t learned how to do it yet. It’s a skill that can be learned. I think it becomes a really easy excuse. I’m tech challenged. Do this for me. Grandson, I don’t know how to do this.

Here’s my phone, make it happen. I’m like, no, stop handing that control over. You can learn it. Stop using that. It’s an excuse.

There are foundations for the fear like when I referred to us as digital immigrants. It’s like a real term that we used in educational technology. We were not born with an iPad.

We weren’t born just hitting the buttons and see what works. We could break the thing. We could break the piece of equipment we had, whereas now, you really can’t break a computer.

It’s a matter of just being flexible and saying, those fears were founded before and now, they’re not. I’ve got to give this a try. I see it in my group all the time.

When somebody comes in and is so excited cos they made something work in their email service provider. I’m like, see, you can totally do it. It just takes a few kinds of successes to get people over that hump.

I think there are certain personalities that seeks that challenge out. I’ve always used technology. I had to use it in my job. I was on university campuses, so I felt like I had to keep up and know what was going on.

I had to know what Facebook was. I remember asking what Facebook was one time in a meeting and I instantly knew that I shouldn’t have asked the question.

I sat down when I was unemployed. I was going to DIY my whole business. I said I’m going to build a website. I sat with that thing for about 48 hours and said if this is what’s running a business, it is not for me, the website.

There’s a personality that loves that backend detail. I think I’m more right brained than that. But anyhow, yes, it’s doable.

Another thing about today is there are so many places to go to hire affordable help. You can go to,, pretty much anywhere and have your thing built for a hundred bucks.

It’s very affordable and doable. In fact, I teach in my audience, in DIYing your business, you really shouldn’t be the expert of everything. That’s not an effective way to run a business.

You really should be focusing on your own kind of zone of genius. I know that’s a cliché, but like if you love WordPress, definitely go do it yourself.

Don’t you know there’s no business where everybody is an expert in all parts of it. That’s why companies have departments in marketing department, accounting department, because we need experts in each thing.

Coming up with your business idea

When working out what a client’s business idea could be, I take them through an exercise and we just go back to the very beginning where you literally write down everything you love to do, everything you’re good at, everything other people ask you to do. That’s how I help women decide what to do in their business.

I ask them, if they’ve had a job, what did you do in that job? What skills? Because sometimes people will say, I’m a fundraiser. They will say the job title, but I ask, what did you do in that job?

For example, as a fundraiser, you had to reach out to people, you had to be a great communicator or you had to ask for money, all of these things. There’s underlying skills that come with that.

I have them do that and start keeping kind of a journal or a log for about a week. I did this exercise first when I was laid off because I had no idea what I wanted to do because I had worked in educational technology and ESL which for me is not like an entrepreneur job right there.

I wound up with a whole notebook. It was everything from my love of speaking French, love for dogs, being organized and more.

It just went on and on and it seems kind of silly at the time. Out of that brainstorming, I had always loved writing and I had done freelance work for magazines in my much younger days. Out of that came the idea for my first business, which was an online magazine which I don’t have any longer through life circumstances, but that’s what led me to that. I loved writing, I loved magazines. I’m going to do that for my hometown.

You could really come to ideas in so many ways. I have a woman in my group who has always loved dogs and became a dog trainer. But when she started having grandkids, she saw the dogs and the grandkids doesn’t mix very well together and she started figuring out how to train families to be able to handle and put dogs and kids together without having any problem.

There are a million things we can do and basically anything is possible as a business. On the internet, you just have to figure out the skill. I call it the mashup, where you have an inventory of things they do not want to do too.

A lot of times women think, I was in finance my whole life so I’m starting my own business which should be related to finance even if they were done with finance when they retired or quit.  Let’s find something you love to do. You want to make sure you include those things you don’t want to do and you just start making these mashups.

I just start having them mash things up and you’d come to get like maybe two or three ideas and that’s when you start researching. Is this possible? Are there competitors? Which do you want? Who’s doing this? Who’s doing something like it? That’s where we start. It’s really inventorying everything about you.

For those women who’ve been at home looking after their family, I remind them they have actually acquired all these skills like budgeting the household, organizing schedules, among many others.   That’s why I often say to people, what do people ask you to do all the time?

Are you the one that gets asked to organize the family reunion every five years? Those are things you’re good at. Now, whether you want to do that as a business is another thing. But we have to get to the skills that you have and the things that you love to do.

Validating your idea

The first step is to validate your idea, do a lot of research, find the competition, find potential customers, which by the way are not your family and friends! Go actually talk to people who would potentially pay for this service and you can find them online. You can find them in your community and really dig deep and find out what they like and don’t like about the idea.

how to start a business

I always encourage my women to start with a presence on Facebook with a Facebook page which is free and easy. Start building an audience there again with potential ideal customers and test your ideas there. Start putting stuff in front of them like what hits and what doesn’t, what gets engagement and what doesn’t.

Start building an email list by offering freebies or creating opt-ins which is a great kind of measure for your idea. If people want this freebie or opt-in, then it’s obviously valuable.

People want to know about it, they get on your list. Now you have this customer list that you can also start putting ideas in front of.

Even then you want to potentially sell a minimum viable product like a mini course or a workshop that you can just further validate. Once you have validated the idea, then you want to start thinking about your messaging, brand, business name and all of those things.

Because you can’t figure any of that out until you’ve talked to customers and had interactions with them. It’s not the other way around.

What I have learned for myself from what I do over the last few years is nothing is as easy as we think it’s going to be. You have to be prepared for a lot of ups and downs in entrepreneurship.

I try to be very frank with my audience about that. I know there’s a lot of people out there that sell the dream but in midlife and beyond, we know there’s no such thing as a free lunch.

I think the biggest thing I learned was it was way more challenging than I thought it was going to be. But also overcoming those challenges has turned out to be a great thing in my life.  It just brought purpose to my life and gets you out of bed in the morning.

I had always been a self-starter. I had worked from home. I had worked remotely that’s why I have that self-discipline. I think for a lot of people who had been like in an office type environment or going to some place to work, that kind of self-discipline is the biggest challenge.

Building businesses and becoming a widow

What kept me going after losing my husband, being laid off and starting two businesses in the last three years is the idea of not knowing what tomorrow brings because you just get through each day with it.

He was sick for a long time, so I really had to take a long time off to take care of him.  That’s actually when I had my first business which was when I decided that first business may not be the best choice because it tied me to this specific location.

I was able to cope, firstly because I was able to take the time off to be with him. I don’t know how that would have worked had I still been corporate. It would have been much trickier. When you’re going through it, you don’t know you’re going through it. Once it happens, you get kind of in survival mode. About six months after is when it really kicks in and that’s when you start going through the stages of grief.

I was really pissed for a while. I was pissed that I had to figure out homeowner’s insurance and I had to take the car for the oil change and all this stuff that you’re going to get done. You have to figure it out for yourself and you get really resentful.

You get past a point where you start to see opportunities. You start to see the silver lining. Now when I’m alone I can go anywhere I want. I can do anything I want. Not that I don’t miss him, but I’m starting to see the opportunity.

I’m thinking about moving, which I never would have done before. I’ve gone on vacation and done things that he never would have done, and he wasn’t into at all.

I think it’s more, when you’re in it, you’re in it so you don’t even see outside of it. It’s only when you get kind of past it like, and it’s in the rear-view mirror that it catches up with you a bit. I still have a lot of moments that I’m like, God damn it.

Where is he? All right, I need to put in a new sea wall at my house and the contractors are not great speaking to women and he was much better at that. Sexism is alive and well too. Then you start to create a new life, which is not easy, but it’s also an opportunity to re-invent, so to speak.

Creating my business helped me in a couple of things. One, now it’s more important that I stabilize my finances. I have all the time in the world to work on my business, which is a good and a bad thing because I work on it a lot and people say I’m always online.

I don’t recommend that. I recommend you have a life so you can really hyper focus on it. It’s also very freeing because I can work on it all of the time. I’ll go sometimes like 10, 14 days all in.

It’s all work and then I’ll be, okay I need a break and then that’s three days off and I’ll take a weekend or whatever.

I have a lot more time to spend on my business than I know a lot of people do because you have responsibilities and all of that. I just have my two dogs right now so it’s a bit easier.

I’ve also used it as a catalyst for change and moving me forward. I’ve raised the bar in my business. I have the time to devote to that now and it’s become my thing.

I’m 52. A lot of my audience are older, like sixties and seventies.  There’s a generational thing that when you lose your husband, it’s more difficult, if you’re 60 or 70 right now, because there’s an imbalance of labor at home.  You just have to figure it out.

I think this is awful to say, but one of the biggest mistakes I made in the beginning was I joined some widow groups on Facebook, and I was there for about a month. Then I thought I have got to get outta here.

This was just depressing because they all talked about how paralyzed they were, how their life was over. I can’t have that for myself.

You have to find a reason to look forward and it does suck. There’s no doubt about it. You have to find a way to start making a new life even if it’s changing habits like your morning coffee habit or silly things. You have to find a way.

But I will say there’s help out there. There are resources for women who find themselves widowed. Don’t take up a sidecar role in what’s happening in your life and finances; know what’s going on. It’ll be a lot easier. Make sure your affairs are in order.

Like in the US, if somebody dies without a will, it can become like this big probate mess. Make sure that’s all in order in advance. These are things I know people don’t want to talk about.

I’d say my number one piece of advice is take responsibility now for knowing what’s going on. If you find yourself in that position, reach out for help because there is help. You have to know that now it’s up to you to create a new life.

I think it’s a long process because you don’t realize how your identity is part of somebody else’s. When that comes apart, you have to find yourself again.

I think that’s the hard part and the opportunity part. I’m guessing there are many reasons for women to start businesses.  This is certainly a situation where starting a business is a really proactive way of creating a whole new life.

There are so many benefits like finding yourself again, finding your passions, getting a reason to get out of bed in the morning, stabilizing finances because you have to be putting yourself out there, you have to be learning new things. You can’t just pull up in a ball and close yourself off from the world, so I think it is definitely a great catalyst for that.

Probably six months ago I would have said no to talking about this, because I would have been in meltdown mode, but I’ve moved along a little bit. I still have the meltdowns but they’re better. I appreciate being able to talk about it because I think it’s something that we don’t talk about enough. It’s very taboo to talk about it.

Like when you said it happened early in my life. One of the things that happens is the whole dynamic of your life changes. Even with friends, because you were a couple before and now you’re single. Somebody put it to me that I’ve held up a mirror to others of what’s coming because I lost my husband early.

People look at people like me and realize, oh shit, that’s going to happen to me one day too. You’re kind of holding up a mirror. I kind of take that almost as a challenge to do it well, so to speak, to reinvent well and show people that they can do it too.

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