Lessons from a Glamorous Entrepreneur

When you meet entrepreneur, Jennifer Grant, the first thing you’ll notice is that she’s immaculately dressed — complete with bright red lipstick and nail polish, high heeled shoes, and a striking haircut. The second thing you’ll notice is that she’s high energy.

Entrepreneur, Jennifer Grant

Entrepreneur, Jennifer Grant

She’s like a bright red Ferrari.

But a key lesson she’s learned is that even though energy and drive are important for an entrepreneur, it’s also important to put the brakes on when necessary. Jennifer says her high-octane personality has been one of her greatest assets in business and also one of her liabilities.

Sometimes the Ferrari has to drive through a school zone.

 

High energy as an asset

Jennifer is an executive coach, professional image consultant, personal brand expert, and keynote speaker. Less than a month after retiring from a 27-year airline career, she’d decided to start Jennifer Grant International — and she had the get-up-and-go to do so.

Although she wouldn’t generally recommend launching a business right away after transitioning from a long-time career, she’s nevertheless glad that she hasn’t just stopped working and retired to the golf course:

“I’m proud that I got started. It takes guts to start a business. I’m proud I’m still doing it, despite the obstacles. And I love feeling that I’m making a difference in people’s lives.”

As well as her energy giving her the stamina to get her work done, she says:

“I think people are drawn to my energy. They also find me approachable, genuine, and caring. I really care for people.”

Her driving ambition helped her through some tough battles in the early days of her business. She persevered and learned that she’s resilient:

“No matter the obstacle or the setback, I can pick myself up.”

 

High energy as a liability

When she started her business, Jennifer was racing solo, without enough careful thought and without seeking advice and support from others. She says, “I operated in my first couple of years on pure intuition.”

Despite some business gurus’ recommendation that you should ‘trust your gut’, Jennifer learned that this is not a good way to make business decisions.

She launched her business with an idea and an instinct… but it turned out people didn’t understand what she could do for her clients. Even her husband didn’t really get it.

Because she forged ahead without understanding her market, and without a plan, she ending up spending a lot of money — all her retirements savings, in fact — without getting the results she dreamed of.

We’ll learn what she wishes she’d done differently instead of charging in like a Ferrari in a china shop, and not slowing down for any curves in the road.

 

A little quiz

Before we get to the lessons we entrepreneurs and business owners can learn from Jennifer’s experiences, here’s a quick quiz:

Which of these statements about Jennifer is NOT true:

  1. She got married on an airplane.

  2. She owned a travel agency in her 20s.

  3. She completed an Ironman when she was 48 years old.

  4. She swam across the Georgia Strait.

  5. She took her parents on her honeymoon to Hawaii.

The answer is at the end of this post.

 

Jennifer’s lessons

Lesson Number One: Understand your market and have a plan (including an exit plan)

As an airline manager, Jennifer helped countless people advance their careers. She advised them on how to dress, and also coached them on how to behave in different professional situations — so they could always give the best impression of themselves. She wanted to turn those skills into a business.

When she started her business, it was natural to Jennifer that she become an image consultant. For Jennifer, professional image is much more than just the clothes someone wears. It also involves someone’s professional interactions with others. Attending or chairing meetings, business negotiations, interviewing or being interviewed, giving presentations and speeches, networking, mingling at convention social events — Jennifer helps her clients with them all.

All this was obvious to Jennifer, but:

“I didn’t realize how hard it would be to move away from my ‘brand’ as Jennifer the Jazz Airlines manager to this new version of myself… I assumed the vision I had for my business was something that everyone else would be able to see. I thought everyone would ‘get it’. But I found that when I introduced myself as an image consultant, people would think, “Oh, you dress people”. I thought that term would encompass everything I could do for my clients.”

If Jennifer had done in-depth market research, she would have been forewarned about how people might misunderstand what she was planning to do, and that would have helped her get clearer on how she should have — and should not have — spent money on her business. She eventually re-branded as an executive coach and image consultant, which helped people understand.

“I work with professionals who want to advance their careers. This can involve refreshing their image (grooming, dress, style, speaking skills, body language, etc.), personal branding, confidence building, business etiquette, networking, and so on. I teach clients how to differentiate themselves from their competition so they can be more confident, respected, influential, prosperous, and successful. And I help clients prepare for public speaking, keynotes, and other presentations.”

If Jennifer were to start her business over again, she would take steps to understand her market better and then she would handle her finances differently. She was reluctant to take out a loan or to seek investors in order to finance her business. Instead, because she was determined to ‘go it alone’, she spent her retirement savings in the first three years of her business.

“Have secure financing to fund the business for at least the first 6 months. Don’t just do it on a song and a prayer.”

Because she didn’t have a clear plan, Jennifer was zipping around from shiny object to shiny object, always thinking that this was the thing that was going to take her business to the next level.

Jennifer has always been an ambitious, hard working, high achiever.

Jennifer has always been an ambitious, hard working, high achiever.

Spending all her retirement savings was a wake-up call, though. She realized that failure was a real possibility — something she hadn’t even imagined before. “I didn’t even think for a minute that anything bad might happen.” And not having a plan for how to ‘get out’ added to her stress.

If she were to do it over again, as well as having a clear business plan spelling out how she was going to finance her business in the early stages, she’d also have an exit strategy. Now she has one — just in case:

“The exit strategy is intended to mitigate the losses of total business failure. Because there is so much emotion involved with entrepreneurs who have given everything to pursue their dream business, an exit strategy is intended to help an individual to remain calm, follow the exit plan, enlist a support system and eventually accept that it was the right decision to let go.”

Even though Jennifer is now past the difficult start-up days, it nevertheless provides her peace of mind to know that she has an exit strategy.

 

Lesson Number Two: Get help and advice

One of the things Jennifer discovered in the early days of her business was how much she didn’t know. But she’s not someone who finds it easy to ask for help.

“I fit the mould of an entrepreneur who not only had to do everything by themselves, but I was also afraid to ask for help. I didn’t want to be regarded as someone who didn’t know what I was doing. I kept all of those questions and worries to myself.”

She eventually had to make some mistakes before choosing to seek a mentor:

“If I were to do it again, I would invest in a business coach sooner. I waited over three years to do that, but it’s probably one of the best investments I’ve ever made.”

She recommends:

“Get as much guidance and support as you can. It was just me by myself going, ‘I’m driven, I’m going to do this.’”

As well as getting help dealing with the practicalities of running a business, Jennifer also recommends getting help with the psychological issues that many entrepreneurs deal with.

Jennifer had a business partner when she founded her first business. Starting her second business, she did everything by herself.

Jennifer had a business partner when she founded her first business. Starting her second business, she did everything by herself.

In the early days of her business, Jennifer struggled with imposter syndrome. One of the things that helped her battle it — along with the support of her family and friends — was connecting with top image consultant, Gloria Starr.

Jennifer went to Florida for eight days to train with Starr, and Starr was so impressed with Jennifer that she soon told her that she didn’t need the training, because she was already so advanced. Jennifer says,

“She validated that I had all this experience and knowledge. She really helped me with my self-esteem and self-confidence, and renewed my belief in myself that I could do this.”

Jennifer says that although friends, family, professional peers, and teachers in your industry can help you get over your imposter syndrome, don’t hesitate to get professional psychological help if you need it.

 

Lesson Number Three: Take work-life balance seriously

Discipline keeps the Ferrari under control. If she didn’t have the discipline to schedule time for things other than her business, Jennifer says it would be easy for her to end up working all the time, like she did during her airline career.

Jennifer enjoyed her long — but demanding — airline career.

Jennifer enjoyed her long — but demanding — airline career.


When she worked for the airlines, Jennifer didn’t physically and mentally take a Christmas Day off in 27 years. She would get up at 4:30 a.m. every day and work until 8 or 9 o’clock at night. Not anymore.

Now, because she runs her own business, she has the freedom to set her own schedule and control how she spends her time.

She’s still an early riser, getting up at 4:30 in the morning, even on weekends. But she doesn’t start work right away. Instead, she prioritizes exercise — either a swim in the lake or at the pool, or a workout at the gym— as she says it helps to keep her healthy in body and mind. She returns home by 6 a.m., and gets ready to start work.

Swimming is an important part of Jennifer’s life. She often swims in the lake, sometimes before the sun is up.

Swimming is an important part of Jennifer’s life. She often swims in the lake, sometimes before the sun is up.

Even if she’s working from her home office, Jennifer gets herself in the right frame of mind by wearing work clothes — which for Jennifer, includes high heeled shoes at her desk. She says it puts her “in business mode”.

“I schedule my social media posts for an hour or so. Then I attend to any client meetings for the day. And any meetings I have, I always make sure I follow up afterwards. I send thank you messages to event organizers, for example. I’ll check in to see where I’m at with the goals I set the previous week with my business coach. I work on my active projects, such as a speech I’m preparing. And I prep for the next meeting with my business coach.”

She makes sure she takes a proper 45-minute break at lunch time, away from her office. And, unless there’s the occasional pressing deadline, she closes her laptop at 6 p.m., and spends the evening relaxing with her husband, reading, and meditating.

“I find work-life balance much easier now than when I was in my airline career. I did experience burnout and it affected my mental health and wellbeing. Now my kids are grown up, it’s not the same pressure and demands of trying to operate a business and trying to raise a family at the same time.”

Jennifer and her husband — with whom she recently celebrated 37 years of marriage.

Jennifer and her husband — with whom she recently celebrated 37 years of marriage.

 

Lesson Number Four: Try video marketing

Along with in-person networking, Jennifer has found social media useful for marketing her business. She says it’s hard to be patient, but she tries to remember that marketing is a long game. It takes time to build a connection with potential clients.

“I’ve found it helpful to be more conversational on social media. It builds trust. I want to give value to people, so I love to give away tips.”

Jennifer in her home studio where she films her videos.

Jennifer in her home studio where she films her videos.

She also highly recommends video marketing. She was nervous about making videos at first — as most people are — but she’s gotten good results from them. She gets interaction on social media and enquiries from potential clients.

She says it’s good to approach video with a spirit of experimentation. Get started and learn as you go along.

“I’ve been doing videos for only about 7 months. I didn’t do them in the first three years because I was afraid of doing them. I’m quite extroverted, but I was over-complicating things. I was thinking, ‘I’m never going to get this. I don’t have the right equipment.’ And then one day, I thought, ‘Just get over yourself’ so I sat down and did my first video… I look back at my early videos and I can see the progress I’ve made. I feel proud of that progress. I’ve had some good feedback on my videos. But I know I have so much more to learn!”

She warns that you shouldn’t expect perfection — the important thing is to connect with people in your videos. Imagine you’re talking to directly to a specific person. That connection is more important than a perfectly executed video.

She recommends thinking about what people want and need, what their problems and obstacles might be, and that should guide the content of your videos. She says it’s also a good idea to practice making a few videos before you start publishing any:

“Just do it. Just start. You don’t have to put it out there right away. First of all, just get used to seeing yourself and hearing your voice.”

  

To sum up, here are Jennifer’s four biggest lessons:

  1. Understand your market and have a plan (including an exit plan): Don’t spend money on random things. Do research and create a plan so you can spend wisely.

  2. Get help and advice: Even if you’re a solopreneur, don’t build a business alone. It’s smart to learn from others.

  3. Take work-life balance seriously: Burnout is bad. Be disciplined about scheduling ‘life’ stuff such as exercise and time with family and friends.

  4. Try video marketing: Be brave! Practice by making some videos that you don’t post. Connecting with your audience is more important than making the perfect video.

 

And, finally…

Here’s a photo of Jennifer and me after I interviewed her.

My excuse is that it was a wee bit breezy that day.

My excuse is that it was a wee bit breezy that day.

If Jennifer is a bright red Ferrari, I am clearly a bicycle. I like to imagine something like this shiny one…

Please tell Santa I would actually love to have this bicycle.

Please tell Santa I would actually love to have this bicycle.

… and not, as my daughter suggested when I mentioned this metaphor to her, a penny farthing.

Apparently, in 1886, this pair rode from San Fernando to Irving Ranch in California (about 70 miles/110 km).

Apparently, in 1886, this pair rode from San Fernando to Irving Ranch in California (about 70 miles/110 km).


Oh, before you go, remember the quiz at the beginning? Here it is again:

Which of these statements about Jennifer is NOT true:

  1. She got married on an airplane.

  2. She owned a travel agency in her 20s.

  3. She completed an Ironman when she was 48 years old.

  4. She swam across the Georgia Strait.

  5. She took her parents on her honeymoon to Hawaii.

If you’ve been paying attention, you’ll have seen some clues. The answer is that (5) is false. In fact, Jennifer brought her parents along on her honeymoon to Las Vegas. The others are 100% true.

If you enjoyed this story about Jennifer Grant and appreciated her advice, please share it so others can learn from her experiences too. 

I’m grateful to Jennifer for graciously allowing me to interview her and to share her story and advice — thank you, Jennifer.

Many thanks to my writing group colleagues who gave me helpful advice on an earlier draft: Danielle Benson, David Crawford, Joyce Kunzelman, Donna Nelson, Jaki Sawyer, and Danusia Tarr. I didn’t take all their advice, so if there’s anything you don’t like, you can definitely blame me. ;)

business, entrepreneurshipZena Ryderentrepreneurship, business1 Comment