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Launching a Business to Teach People Digital Skills: Jessica’s Story

Published on 01/30/2017

Jessica Jolly cover photoBeing laid off after 28 years and some self-development classes led Jessica to discover her talent for coaching others to learn Microsoft Office programs like Word, Excel, and Powerpoint. She recently started her own company, Alt-Enter, where she trains adults in those and other digital skills. 


Tell us a little about your background.

I grew up overseas, in Africa to be precise. My father was initially in the Foreign Service and then in private business. We lived in Sierra Leone, Zaire (now the Congo), and then back in Sierra Leone. I came to the US for boarding school in 7th grade, enrolled at the University of Chicago for college, and have stayed in Chicago ever since. I made the typical trek north: from Hyde Park (where the University is), to Rogers Park (the northernmost neighborhood in Chicago), and finally to Evanston, the first suburb north of Chicago. I have lived in Evanston for over 20 years.

Jessica Jolly age 4

Age 4

Both my parents and my two brothers (and their families) live on the East Coast, so I don’t see them as much as I would like. Frankly, I envy families who have stayed in the same geographical area.

I worked for Unilever, a global consumer products company, for 28 years, which was a wonderful experience. I was a Facilities Manager, then transitioned to a consulting role after a layoff. I loved almost every minute of my employment in Corporate America. I was good at the office politics and the complex processes and procedures.

I have been married over 30 years (to a wonderful man I met as a sophomore at the University of Chicago), and I have a 25-year-old daughter. She lives in Evanston as well, with a wonderful young man, so we see her at least once a week, which is great. I have two terriers that keep me very busy with the required amount of dog walking! Good thing I have an enormous amount of energy.

Our family at the State Fair when our daughter was little

Our family at the State Fair when our daughter was little


When did you start to think about making a change in midlife?

When I was laid off from Unilever, I realized that I had let some of my technical skills atrophy. I had gotten too “comfortable.” I embarked on a self-study program for Microsoft Word, PowerPoint, and Excel. As I got better, I started answering questions at my local public library, where I volunteered. At some point, the Branch Manager at the Evanston Public Library and I decided to hold a “Tips and Tricks” program on MS Office. This was very successful, and we started refining the model (how long each program was, how often it was offered, the agenda for each program). Eventually, the main branch of the library became interested in the programs, and we launched a larger, more formal program there, teaching MS Word, Excel, and PowerPoint in multi-week series. All of these programs were free and I was conducting them on a pro-bono basis.

It was around this time that I started to think about starting my own company, but I was still very happy working as a contractor for Unilever. I did decide on a name, in case I ever were to start my own company.

Jessica Jolly Working in Bangalore, India while at Unilever

Working in Bangalore, India while at Unilever

In April of 2015, Unilever decided to “insource” my role to the U.K. A wonderfully capable young woman was hired, and I had the task of “handing over” my knowledge, processes, and historical materials over to the team in the UK. This was a bittersweet experience, made easier by the fact that they were sorry to see me leave, and I genuinely wanted them to succeed without me. Also, I once had a boss who instilled in me the importance of being as good on the last day of the job as on the first day. This admonition has stayed with me, and informed my leave taking. And I am pleased to say that they didn’t have a question about anything until nine months into 2016!

I started looking for a new job in mid-2015, but noticed that my heart really was not in it. I wanted to decide my own priorities, and be valued because of my gray hair, not despite it. In mid March 2016, I made the decision to start my own company, using the name I had selected several years earlier.

Jessica Jolly Teaching Microsoft Word at the Evanston Public Library

Teaching Microsoft Word at the Evanston Public Library (photo credit: Lynn Troutmann)


What is your next act?

I am the founder of Alt-Enter, which I launched in July 2016 at the age of 53. As I mentioned above, I had already picked out the name several years earlier. It comes from the keystroke used to force a line break in an Excel cell. I chose it because of an experience I had when teaching a seasoned Excel user. I was showing her some very advanced things in Excel, like pivot tables, and then I used ALT-Enter. Her face lit up, and she was so excited. It turns out that this keystroke combination solved a problem she had been struggling with for a while.

My business is teaching people digital skills, focused primarily on Microsoft Office products (Excel, Word, PowerPoint, OneNote, and Outlook). I teach adults who want to improve their digital skills for various reasons:

1) Perform job-related tasks more efficiently and more effectively

2) Gain skills necessary to get a new job

3) Participate in hobbies such as photo organizing

4) Share files and communicate with friends and family

I provide individual coaching and group classes. I try to match the format with the needs of the student.

What I love about this business is seeing the look on people’s face when they realize that they “get it”—they understand something that they didn’t think they could. I strongly believe that everyone can learn to use these and similar programs (such as Google Apps). I do not believe that these skills are the province of the young. In fact, I believe just the opposite: the more you have learned in your life, the easier it is to learn something new.

Jessica Jolly Teaching "Scary Functions" on Halloween

Teaching “Scary Functions” on Halloween


Why did you choose this next act?  

I never had a burning desire to be an entrepreneur. As I mentioned, I was very happy working in a large corporation—I thrived on navigating the size, bureaucracy, complexity and politics.

However, at this time in my life, I did not want to start over. I know that there exists a cult of youth in many large organizations, who prefer to hire young graduates and train them. I didn’t want to fight the uphill battle to prove that my experience was valuable, not a handicap.

I had been turning this option over in my mind for several years, so when the time came, going in this direction felt natural.


How hard was it to take the plunge?

It wasn’t hard to take the plunge at all. However, I will say that at various points over this past summer I have realized that every step I take forward locks me into this path a little more. That realization stops me in my tracks (mentally) every time I have it. But then I just shake it off and keep going.

I did several things to prepare to be a successful small business owner:

I took a 12-week class on starting a small business (see Resources below). I cannot stress enough how important it is to educate yourself on the ins-and-outs of owning a small business. Just because you are good at what you do does not mean you will be good at running a small business.

I obtained certification from Microsoft in the Office programs, and joined the Microsoft Certified Trainer program. Membership in this program has given me access to a network of fellow trainers, small business owners, experts, and content. If you are planning to position yourself as an expert in something, find the other experts and join their organization. Expertise is not a zero-sum game; they can be an expert, and so can you!

I became certified in QuickBooks Online, because I knew that I would be using this software to manage my business’ finances, and could also develop this as a line of revenue.

I sent an email out to friends and family, notifying them of my intention to start my own business. Taking this step helped me state what my business goals were and why I wanted to do this. I remember hitting “send” on the email and thinking, “Well, that makes it final!” It was a way of drawing a line in the sand for myself.


Jessica Jolly Graduating from the Sunshine Enterprises Program

Graduating from the Sunshine Enterprises Program


How supportive were your family and friends?

My friends and family were very supportive. While I always accept the possibility that I can fail, my support network has unflaggingly bolstered me. I don’t always agree with their very optimistic view of my business, but it is nice to hear it nonetheless.

While support is always welcomed, I have valued even more the constructive critiques offered by some. I have one friend who was brave enough to offer real criticism of my business card. She told me that she didn’t know what I was selling with the card that I had. (Keep in mind that I had already spent a lot of money on the card, and was proud of it.) But she was absolutely right. She and I re-designed the card, completely, and I couldn’t be more grateful to her.

Jessica Jolly old business card

My old business card

Jessica Jolly new business card

My new business card




What challenges did you encounter?

For me, the biggest challenge is patience. My business is essentially a word-of-mouth referral model, and it will take time to develop the referral network. During this time, I have to keep trying as many different advertising and marketing tools as possible. For example, I recently created a Facebook ad, spent $50 and got one hit. So now I have to figure out if the ad itself was ineffective, if the program was not interesting, or if I targeted the wrong audience.

This leads me to the second biggest challenge. As a small business owner, you have to be everything: worker bee, bean counter, cheerleader and janitor. There never seems to be a time when you are in a comfort zone. Because I am in Technology, I have to spend at least one hour a day on Research and Development. I love learning something new, but learning something every day can get a little tiring.

Finally, everything I do needs to be an example of my capabilities. If I send out a proposal, it needs to be a perfect document. If I post on LinkedIn, it needs to be something fresh and on-point about technology. These are high bars to clear on a regular basis.

And sometimes I don’t clear them. I still need to refine my website, based on recent constructive critiques. This is after re-designing it completely, based on another constructive critique. I am sure this will continue as I grow and my business grows. Be open to helpful critiques; they will help you far more than empty praise.


Were there times when you thought about giving up?  

No, I haven’t thought about giving up. I know that the alternative (going back into a corporate role) would present its own challenges. I realized a couple of years ago that there is no “grass that is greener.” There are challenges and hurdles with starting a business, but there would be with anything I do. I have chosen this path, and I am focusing on being present in it.

Pepper, Jessica Jolly's dog


Jengy, Jessica Jolly's dog


What did you learn about yourself through this process?

I realized that in my midlife I have a much higher tolerance for failure and risk than I had when I was younger. In the process of passing some of the expert level exams for certification, I failed several times. Instead of hanging my head, I promptly scheduled my next test. I think that once you have reached middle age, you understand that failure is a label that has no real meaning unless you give it one.

My tolerance for risk has also grown, because I understand now that if I put in hard work, get the right training/education, and network like heck, I am likely to succeed. Maybe not immediately (almost certainly not immediately!), but eventually. Luck does play a role in all of our lives, but I firmly believe that we also play a hand in making luck.


Looking back, is there anything you’d have done differently?

I think I would have started developing my clientele before leaving Unilever. I had the opportunity to do this, but just wasn’t sure that opening my own business was what I wanted to do.

Jessica Jolly with her family

My family now


What advice do you have for women seeking reinvention in midlife?

There is a notion in the U.S. that if you are “following your dream,” you will be happy from thenceforth. That’s not true. Following your path will involve disappointments, triumphs and lots of humdrum activity. Make sure that the path you are choosing is something that you will enjoy during the valleys and the ordinary everyday.

Make sure you are comfortable selling your services. I knew I was in the right business when I realized that I could speak comfortably about how good I was at training (and not feel like I was bragging). Creating your brand is a critical part of starting a new business, and you will spend a lot of time in the first year doing just that. You have to deeply believe that you are good at what you do and that you should be paid to do it!

Be prepared to work hard and feel uncomfortable. Making your living doing something new is scary! It will be a while before you have a reliable income stream (probably), and a while before tasks become easy. In the meantime, make sure you have some restful hobbies (I knit a lot), and exercise every day.

Jessica Jolly At "Open House Chicago" with friends

At “Open House Chicago” with friends


What advice do you have for those interested in pursuing your career/reinvention path?

If you are interested in being technical trainer (of any kind), there are lots of avenues available. Most large tech companies (Microsoft, Google, Facebook, QuickBooks) offer certification options. These are great ways to show that you do indeed know the product.

Once you have obtained certification, most tech companies have great communities you can join. I am a Microsoft Certified Trainer (MCT), and the MCT community is warm, welcoming, and helpful.

Next, get experience teaching. I started by volunteering my services for my library, and I learned a lot teaching a variety of classes over several years. Do not expect that if you are good at the technology you will also enjoy teaching. They are two different skill sets, and to be an effective trainer, you have to like both.

Show up! Go to every networking opportunity, speak to everyone, haunt blogs and websites, comment on other people’s articles and posts. Apply for any opportunity that you are qualified for, even if it is a stretch. I recently got to serve as an Ambassador at Microsoft Ignite (the annual MS show) because, on a lark, I submitted an application. I did not think I would be picked, but I was. Attending Ignite was a great experience. I met lots of great people, found out about a lot of resources I had no idea about, and won a $3200 computer. Should I say it again? Show up!


Jessica Jolly's home office

My home office


What resources do you recommend?

First and foremost, if you are starting a small business, take a small business class. In Chicago, Sunshine Enterprises offers a 12-week class called the Community Business Academy.  Another great resource is the Women’s Business Development Center. I am sure that there are similar resources wherever you are in the country. Look around. I can’t stress enough that even if you are great at what you do, running a small business is a different skill set, and you need to train for it!

Perfect a three-minute pitch and your presentation skills. When you reinvent yourself, you have to pitch yourself and your skills all the time. One book I loved for learning about presentations is Presentation Zen: Simple Ideas on Presentation Design and Delivery by Garr Reynolds. He also has a website packed with tips on how to hone your message and be clear on what your offering is.

Sign up for this blog, Next Act for Women, and read it every time it comes out. I reached out to one of the women interviewed, Sharon Danzger, and she was welcoming and helpful. She is the one who critiqued my original website. Because of her kind prompting, I re-designed the site completely, and it is much better. (It still needs more work, but the time she generously spent giving me specific on-point feedback really helped me!). Check out her website. She has great material there.

Also because of Next Act, I reconnected with another woman, Rebecca Berneck, who runs a business called Officeheads. She and I had met over five years ago, but there wasn’t any real synergy for us at that point in time. When I saw her featured in Next Act For Women, I reached out, we talked, and we are now brainstorming partnership opportunities.

Join your local Chamber of Commerce. You may get business directly from that organization but, more importantly, you will meet other people engaged in this same effort. I met a wonderful woman, Cindy Levitt, who runs an organizing business, Peace by Piece. Cindy was very encouraging, and graciously allowed me to riff on her business name to create my tagline: Building digital skills, bit by byte. Leverage the contacts you can make at the Chamber, but remember, help your contacts first before you ask for anything from them.

If you are comfortable speaking in public, do so. If you are not comfortable, get comfortable! Sign up for the SpeakNet group on Slack. This group is focused on technical presentations, but I am sure there are similar resources out there for non-technical speakers. And don’t be afraid to set a stretch goal. Sign up to be a speaker on something that you are comfortable with, then use the deadline of the engagement to make yourself an expert!

Jessica Jolly's sample list of resources that she use to regularly improve her knowledge and skills in Microsoft and other tech products.

Below is a sample list of resources that I use to regularly improve my knowledge and skills in Microsoft and other tech products.

Public library

Your local public library (or one in the surrounding area) is a great source for books and classes. I teach beginner all the way to advanced classes in Excel, Powerpoint, and Word, at my local public library, all of which are free. Public libraries also have access to great sites for basic digital literacy, and of course, books! Most libraries focus their collection on beginner book series (such as the “For Dummies”) but check out your library’s entire collection.


While I generally like to buy books from independent local bookstores, the only exception I make is computer manuals, which I buy on Amazon. I personally like the Inside Out computer book series but there are many options. If you can, check out a sample of the series you want to buy first, to make sure it has the right style for you.

They are all priced between $25-$40. All of these manuals come with sample datasets with which you can replicate their exercises.


I love this site. Of all the resources I listed here, this is by far my favorite. It is a subscription-based model, but if you like learning from books (and some videos), it is worth it. The breadth of its collection is amazing. Simply search on “Excel” and you will find over 150 videos and 700 books. This is well worth your investment if you are in “learning mode.”


Lynda is a part of LinkedIn, which is now owned by Microsoft. You can expect that this site will start featuring more and more Microsoft material. However, there is already plenty of material on MS Office on the site. Simply enter the name of the program in the Search box, and you will see numerous videos at multiple levels. These are packaged in short videos, with an accompanying transcript.

Lynda is a paid service that costs $25/month or $240/year for the basic membership. To have access to the sample datasets used by the instructor, you have to pay more (although some instructors will provide them gratis). You can follow along using your own dataset. There is a free trial option that lasts 10 days.

Also, check with your public library. I know that my library provides access to Lynda using your library card.


PluralSight is a competitor site to Lynda. It costs $30/month, and I think it is more technically oriented than Lynda.com. With a free trial you could take a few of their online courses during that time.


YouTube has a wide variety of content, from basic to advanced. Because that content is not curated, I use it on a spot basis, if there is a particular skill I want to know how to perform. There are excellent resources on it, such as the channel ExcelIsFun (for Excel).


A Google search will yield hundreds of blogs. Because these are not focused on linear learning, I wouldn’t make the blogs your first stop. But they can be useful on occasion. Here is a list of some that I like:







Google with search terms like “MS Office,” “MS Word,” “Presentation,” and you will find a huge variety of content.

Don’t forget to check out my Bit by Byte Blog. I cover a lot of ground, but most of it relates directly to technology such as MS Office applications.

Community Colleges

If you want to take a deep dive into Excel, you can see if your local community college offers a class. Oakton Community College offers two Excel classes, which are multi-week classes at specific times of day.


Contact Jessica Jolly at Jessica.Jolly@AltEnterTraining.com


Connect with me on Facebook (find out more about my classes and events)

Find me on LinkedIn

Follow me on Twitter: @JBJ2110

HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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  1. Sharon Danzger

    I was SO excited to see this article. When I see “There’s a new post on Next Act for Women!” in my Inbox, I always look forward to reading another incredible story.

    What a nice surprise to see it was my new friend, Jessica! Your article is great…and inspiring. And then, to see a shout out to me was definitely the icing on the cake. Thanks for making my day!

    Let’s reconnect soon; I’d love to hear how everything is going.

    • Jessica Jolly

      Thank you Sharon. I can’t thank you enough for the help you provided me when I reached out to you after reading YOUR post. This blog is so great for connecting women together!

  2. Chevonne Hobbs

    A wonderful article Jessica! You truly are an inspiration to all women of all ages. I admire your strength and your courage, and mostly so happy everything is working well for you after Unilever. Although I miss working with you, it’s lovely to hear and read about you on LinkedIn. I wish you all the luck in the world.

    Best wishes
    Chevonne xx

  3. Morris Edwards


    This is very useful post. Thanks for sharing with us. I like the Control + Enter trick as it saves the time to apply the same formula to other cells by either dragging or copy pasting.


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