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top 3 regrets as an entrepreneur

Big 3 regrets as an entrepreneur

Regrets.

It’s my personal philosophy to live a life without regrets. Which makes it a challenge to share here that yes, I have a few. 

Especially as it relates to the service business franchise system I ran for 20 years. I started from zero in a corner of my basement and built it to a 7-figure system with 5 locations in 3 cities. But even with all that success, I can reflect now and see a few things I wish I’d done differently. No matter where you are in your business journey, avoid these big 3 regrets as an entrepreneur.

1. Underpaying myself

Show me the money.

Clearly, people get into business to make money. And my business did make money. My big regret is that I didn’t put more of it into my own pocket.

Sure, pushing profits back into a business is a smart strategy for growth. 

And yes, paying competitive wages is important for building a strong team.

But how many times did I budget year-end bonuses for my management staff and employees, but skipped out on paying myself? 

Most years, in fact. And why?

There is no simple answer for that. Actually, there is. Basically a matter of where my money mindset was at the time. 

The point is, looking back now this is a big regret. Which may be one of the reasons why as a business coach I always talk about personal financial goals with my clients.

2. Working too much

Big 3 regrets as an entrepreneur

 

How much is working too much? This is very subjective. For some people, a 50-60 hour work week is normal. And they thrive with it.

For others, working more than 4 days a week is too much. 

For me, my regret is that I worked a schedule that left me little time for my own physical and mental health. My own wellness was not a priority. In fact, it wasn’t even on the list.

At the time, I was proud of myself for a strong work-life balance. Mompreneur magazine profiled me as an example of someone who was doing it all – raising daughters and building a successful business. And sure, I had the flexibility to be there when the school bus arrived in the afternoons.

But I also had the flexibility to work on the weekends, and to work after my kids went to sleep, deep into the early hours of the morning.

Most of the time, my schedule was packed with working on the business, managing my household, and looking after my daughters. There was very little time to look after my own self-care. Or to look after my marriage. And ultimately, I lost out because of it. So working too much may be my biggest regret as an entrepreneur. 

After all, having control over the schedule is one of the many benefits of owning your own business. So build a strong boundary between life and work, and schedule time AWAY from the business. This will not just improve the quality of your own life and health – it will also prevent burnout and improve your productivity for the time you do spend on your business.

2. Working too much

Big 3 regrets as an entrepreneur

 

How much is working too much? This is very subjective. For some people, a 50-60 hour work week is normal. And they thrive with it.

For others, working more than 4 days a week is too much. 

For me, my regret is that I worked a schedule that left me little time for my own physical and mental health. My own wellness was not a priority. In fact, it wasn’t even on the list.

At the time, I was proud of myself for a strong work-life balance. Mompreneur magazine profiled me as an example of someone who was doing it all – raising daughters and building a successful business. And sure, I had the flexibility to be there when the school bus arrived in the afternoons.

But I also had the flexibility to work on the weekends, and to work after my kids went to sleep, deep into the early hours of the morning.

Most of the time, my schedule was packed with working on the business, managing my household, and looking after my daughters. There was very little time to look after my own self-care. Or to look after my marriage. And ultimately, I lost out because of it. So working too much may be my biggest regret as an entrepreneur. 

After all, having control over the schedule is one of the many benefits of owning your own business. So build a strong boundary between life and work, and schedule time AWAY from the business. This will not just improve the quality of your own life and health – it will also prevent burnout and improve your productivity for the time you do spend on your business.

3. Not working with a business coach

Yes, this seems obvious, and perhaps self-serving given that now I work as an entrepreneur coach. But it is BECAUSE of my experience as an entrepreneur that I’m so passionate about the value of coaching for small business owners.

I worked with a coach when I started my last business. I’d been in a cushy corporate job which sucked the soul out of me every time I entered that grey floor of stale cubicles. But building a new business felt overwhelming. On one hand, I had such a long list of action items that I didn’t know where to start. On the other hand, I was worried that I was missing something important.

Working with my business coach gave me structure and accountability. She validated my ideas. She gave me insight and advice which pushed my business forward by MONTHS. Her perspective and experience eliminated many operational and marketing mistakes which saved me time and money. The ROI was clear.

So why did I stop working with a business coach?

Maybe I felt that I’d learned enough from her. And that I could manage the rest on my own. Now, I see that a better choice would have been to find a coach that better fit for where me AND my business was at the time. Ongoing monthly coaching calls would have given me perspective and insight which could have prevented all sorts of hassles and issues in my business.

The irony is that if I had kept working with a business coach, I likely wouldn’t have the first 2 regrets. Because a good coach would have checked in that my personal financial goals were being met. And that I was taking the time to take care of me, not just my business and my children.

Guide for entrepreneurs to avoid regret

Each entrepreneur has their own individual set of goals and expectations for being in business. There is no one list that suits everyone. Use these big 3 regrets as an entrepreneur to inspire you to reflect on your values. 

Overall, consider what you wanted to achieve when you first started your business. And not just lifestyle and income. Also think of how often you work, and what you spend your time working on. I recommend using the Vivid Vision process by Cameron Herold to develop a clear set of goals for what you want your business to feel like, look like, and act like.

Then, check in where you are now in your lifestyle, income, work schedule, and business. What doesn’t match up with that vivid vision? Use this to get clear about the gaps so you can make a list of changes to make.

Finally, when doing this review process, don’t dwell on any regrets that may come up. It’s easy to fall into that “should have” and “could have” thinking. However, what is past is past. Embrace the opportunity for change now. Remember the lesson of  hagstones, and how small changes repeated over time have HUGE impact. Celebrate that you are being proactive now in doing the work to make your experience as an entrepreneur everything that you want it to be. 

And of course, if you want structure and accountability to help you with this process, let’s connect to talk about it.

AVOID REGRET with this guide for entrepreneurs

Each entrepreneur has their own individual set of goals and expectations for being in business. There is no one list that suits everyone. Use these big 3 regrets as an entrepreneur to inspire you to reflect on your values. 

Overall, consider what you wanted to achieve when you first started your business. And not just lifestyle and income. Also think of how often you work, and what you spend your time working on. I recommend using the Vivid Vision process by Cameron Herold to develop a clear set of goals for what you want your business to feel like, look like, and act like.

 

Then, check in where you are now in your lifestyle, income, work schedule, and business. What doesn’t match up with that vivid vision? Use this to get clear about the gaps so you can make a list of changes to make.

Finally, when doing this review process, don’t dwell on any regrets that may come up. It’s easy to fall into that “should have” and “could have” thinking. However, what is past is past. Embrace the opportunity for change now. Remember the lesson of  hagstones, and how small changes repeated over time have HUGE impact. Celebrate that you are being proactive now in doing the work to make your experience as an entrepreneur everything that you want it to be. 

And of course, if you want structure and accountability to help you with this process, let’s connect to talk about it.

Big 3 regrets as an entrepreneur Read More »

Can entrepreneurship be learned

Can entrepreneurship be learned?

Can entrepreneurship be learned? This is a thread of the timeless argument of nature vs nurture. Can someone be taught how to start and grow their own business, or are entrepreneurs just born this way? A scan of founder bios suggests the latter.

Afterall, Shopify was started by a photographer, a coding guy, and a jock. Also, Airbnb was founded by two industrial designers and a software engineer. Not one business degree between them. But the answer is not so clear-cut. Because though someone may have entrepreneurial qualities in their nature, it is often due to nurturing that they achieve success.

The Entrepreneurial Nature

First, what does it mean to be entrepreneurial, or to have an entrepreneur mindset? Academics have studied what is different about entrepreneurs, and what they all have in common. Many psychologists use the 5-Factor model to explain personality traits.

Usually known by the acronym OCEAN, it’s Openness, Conscientiousness, Extraversion, Agreeableness, and Neuroticism. The idea is that all personalities can be expressed as a blend of these 5 factors. As shown below, the key behaviours of being an entrepreneur can be explained by the OCEAN model, which supports that the entrepreneurial nature is hard-wired into our personalities.

Risk Taking

All entrepreneurs have a high tolerance for risk. After all, there is never a guarantee of success when putting up cash and capital to build an offering and a team. Being comfortable with a constant level of uncertainty is just part of being a business owner.

According to the OCEAN personality model, this requires a high level of Openness and Agreeableness. Additionally, accepting risk requires a high level of emotional security, which means entrepreneurs tend to score low on Neuroticism.

Self-Motivating

Entrepreneurs make things happen. Especially in the early stages of growth, there is no external force or set of expectations. Businesses are built driven by the motivation of the entrepreneur. This aligns with a high level of Consciousness. Also, with Extraversion, since the process of setting up a business requires getting out there to communicate with new people.

Creative

Most of all, entrepreneurs are creative. After all, entrepreneurship has been defined as “a creative process of identifying and pursuing value-creating opportunities, often in the face of uncertainty and risk.” That involves being curious and coming up with ideas that fill consumer needs and market gaps. As a result, according to the OCEAN personality model, entrepreneurs have a high level of Openness.

Successful Entrepreneurs Who Never Went to Business School

Also making the case for nature vs nurture are the success stories of these entrepreneurs who never went to business school. Clearly, success in business doesn’t require training in business.

Anita Roddick

At one time, she was the wealthiest woman in Britain due to the global success of The Body Shop. Previously, she ran both a hotel and a restaurant. Unsurprisingly, she grew up in an entrepreneurial family. Her mother owned a little cafe in their town, where Anita worked many hours as a teenager.

Martha Stewart

Martha Stewart

Not everyone knows that Martha was a Wall Street broker with a degree in history and architectural history. Her first company was a catering business, and her entrepreneurial nature leveraged her skills in cooking, decor, and design into a global empire. From the first book in 1982, Martha developed a brand identity which is now synonymous with style and good taste.

Jeff Bezos

Back in 1994, Jeff left his career as a hedge-fund manager to open an online bookshop in his garage. Obviously, this grew to become the global marketplace Amazon. While he studied computer science at Princeton University, he clearly had what it takes to be a successful entrepreneur. Particularly, his ability to be creative and tolerate risk. He kept expanding Amazon even though it didn’t make a profit for the first 5 years.

Mentoring and Entrepreneurship

Clearly, it is possible to be successful in business without training in entrepreneurship. However, many high performing entrepreneurs credit mentoring for their success. For example, Y Combinator runs programs which bring expert advice and connections as well as cash to high-potential new businesses. AirBnB, Stripe, and DropBox were once just fledgling startups until the support of Y Combinator nurtured them.

Also, as we’ve seen from shows like Dragon’s Den and Shark Tank, it takes more than cash investment to scale up a business. The input and guidance of someone more experienced can shortcut a path to success. Clearly, mentoring and entrepreneurship go hand in hand. 

Can entrepreneurship be learned?

In my view, entrepreneurship can be learned. Specifically, it can be nurtured and developed. However, there must be a foundation of an entrepreneurial nature and mindset. It’s the same with any set of skills and abilities. For example, a vocal coach can help someone become a better performer, but only if they have a good voice to begin with.

Afterall, even with all the vocal coaching in the world, I can’t carry a tune. Similarly, with training and practise individuals can win Olympic medals or sports championships, but only if they have a baseline of athletic ability. Essentially, any talent can be improved with training. And entrepreneurship is a talent which benefits from mentoring and business coaching.

Can entrepreneurship be learned? Read More »

What it’s like to win a business award

What it’s like to win a business award

Any entrepreneur would love to be named “Businessperson of the Year” or win “Company of the Year. I mean, who doesn’t want to be recognized for all their hard work? I certainly did. When I was growing my last company, I made business awards part of my strategic planning.If you’ve wondered what it’s like to win a business award, read this to get a glimpse of the experience, and how to prepare to make the most of it.

First - Setting the goal

When I left my cubicle corporate life to start my own company, I immediately became involved in the local business community. I joined the Chamber of Commerce, the Better Business Bureau, and networking groups.

Not surprisingly, this involved going to lots of meetings. As in, old-school, get in the car to drive and park and walk into a room of strangers meetings. One event was a gala evening for the Businesswoman of the Year Award. Champagne flowed. There was swag and glitter and local media with cameras. It was a very high profile event in the capital city where I lived. And as I watched the winner go on stage, I set a goal. That one day, I’d win Businesswoman of the Year.

Next - Long term planning

By the time I submitted my 10 page nomination package to the Businesswoman of the Year Award committee, I’d adjusted my expectations. Several years had passed. I was more seasoned both as an entrepreneur, and with award programs. I already knew what it’s like to win a business award. My company had been a finalist for Company of the Year,  and twice won the Torch Award for Business Ethics. Also, I’d been named to the coveted Forty Under 40 list for my city. Although these were rewarding and fun experiences, they were also part of my long term planning.

Actually, these awards were strategic, to boost my nomination package for Businesswoman of the Year. Because by this time, I knew how much publicity and prestige the finalists received in the run-up to that gala event.

Therefore, my goal was to get into that final 3 for the Entrepreneur category. And I did that by building my resume and accomplishments to deliver what they looked for. I evaluated the award criteria and compared it to the profile of the winners.

Accordingly, I made choices which had immediate benefits and also served to support my nomination package. For example, taking on a volunteer leadership role for the board of a local women’s shelter.

Then - the preparation

Every business award event involves preparation. After all, you can’t just roll in like it’s a casual breakfast meeting. These things do tend to be gala evenings. Expect black tie, a 4 course meal, and cameras everywhere. Also, because it’s such a high profile event, there may be local celebrities and dignitaries. So if you’ve ever wanted to shake hands with the mayor of your city, this is a chance to do it. 

Without a doubt, the runup to the Businesswoman of the Year Award was the most exciting preparation I experienced. First of all, there was a photoshoot by a famous Canadian photographer. Coincidentally, that photographer was the very same woman I watched win the Businesswoman of the Year Award all those years earlier – the inspiration for my goal. Also, there were interviews with local media. However, my favourite part was going to a high-end jewellery store to select items to wear on the big evening. These beautiful and expensive pieces would be loaned for the night under very tight security.

What it’s like to win a business award

At last - the Gala

The day of the gala evening was like the run up to a wedding. A tuxedo for my husband. Hair and makeup for me. And a huge sense of anticipation. The loaner ring on my finger cost more than my first car. It felt like a costume party to be so dressed up and out on a school night. We shared my table with friends from the business community. It was genuinely a good time, mostly because I had no expectation of winning. After all, I’d reached my goal. It was this – the publicity and credibility of being Finalist, and the fuss and celebration of the Gala. Another Finalist in my Entrepreneur category had been in business much longer, and I believed she would win.

Finally, the moment for my category arrived. From the podium, in front of hundreds of people, my bio along with the 2 other Finalists were read out. Meanwhile, footage of pre-recorded interviews flashed on the big screen above the stage. The moment they broke the seal on the envelope, I knew they’d be calling my name. And then, they did. They called my name. Immediately, everyone at my table jumped to their feet, and a TV camera was in my face. I made my way to the stage reaching for balance in my high heels and for words to say. I had not prepared a speech. Meanwhile, from the table, my friend and marketing expert Deanna White quietly clicked “send” on a press release. The news of my win hit the inboxes of key media contacts before I even got to the podium.

Being the winner

The next couple of days were surreal. In large part to Deanna’s preparation and marketing expertise, my win was covered by local media. Taking my youngest to school, the crossing guard called out “Congratulations!”. Several parents and teachers approached me to say the same, and ask questions about my company. Floral deliveries arrived at my office. My email was flooded with congratulations from almost all my contacts, and from people I’d never met.

Naturally, by the time the flowers were wilting, everyone had moved on, and things went back to normal. Nevertheless, I had the pleasure of keeping the Businesswoman of the Year Award in my office for a whole year. And like the Stanley Cup, my name is still on it. Though it was truly a surprise to win, it was a deeply rewarding and affirmational experience.

What to expect from participating in business awards

There are many reasons to include business awards in your strategy. Perhaps it’s to raise the profile and visibility of your brand. Also, it may be used to strengthen a pitch for investors, or attract a buyer. In any case, here are some tips on what to expect from reaching the short list or finalist stage, and what to expect from winning a business award.

More sales pitches

As soon as you and your company hit the list of nominations or finalists, expect more email and calls. Some will be spammy, because bots scraped the web and added you to email lists. However, many will be local, and personalized. From SEO specialists to investment advisors to graphic designers, you are now on the radar of businesses looking for new clients. Be open to these opportunities to expand your network. After all, a higher profile is one of the reasons to get involved in business awards.

More work

If you thought preparing the nomination form and submission package was the end of it, think again. This is one thing about what it’s like to win a business award; it does create more work. So expect more leads and customer enquiries. Clearly, this is one of the benefits of doing it in the first place. Therefore, prepare ahead so there is capacity for this extra work. Furthermore, there is the work involved to fully leverage your win. For example, updating marketing material, social media profiles, and client communication.

More attention

You may hear from people you forgot you knew. Of course, the level of attention correlates to the profile of the award, and the skill of your publicity person. Regardless, expect more attention from people seeking a mentor, business advice, or to ask about your business.

More expenses

Being part of a gala evening costs money. So in your strategic planning, build that into your business budget. After all, the tickets are not free. Buying a table is the norm, so you can share the event with a spouse, business partner, key employees, friends, and colleagues. There may be babysitting costs, transportation, hair and makeup. Obviously, there is the wardrobe. Men have long had formal wear rental options available. Happily, this is now available for women with companies like Rent The Runway, which has a category just for award season.

A slump

After the rush and excitement of the award ceremony, the win, and all the attention, expect a bit of a slump. After all, there may have been weeks or even months of anticipation and buildup. Especially if the awards had been part of your long term strategy. And just as there are post-holiday blues, the same deflating feeling may creep up. Seek the support of your inner circle, and look for a new project to occupy yourself.

Preparing to win a business award

Clear time in the schedule after the winners are announced. Have your marketing plan prepared and ready to go. Prepare to bask in the glow of the winning spotlight. Also, create the space to take advantage of the opportunities your award brings. Book those meetings to expand your network. Broadcast the win across all social profiles. Add the award to marketing material and messaging. Oh, and prepare a speech, just in case. For a full list of how to leverage your win, see “Are Business Awards Worth it?” 

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Rebecca Page-Chapman