Category: Blog

A lot of the reasons entrepreneurs struggle, frankly, I think, are mental.

I myself have given up in the past because I stopped believing in myself and my idea.  Or maybe to be more accurate, I never really quite believed in myself to begin with.

And I’m fairly sure I’m not the only one.

Being a successful entrepreneur is largely about being a successful salesperson. People think about the sales aspect of starting a business when it comes to pitching — pitching to investors, pitch competitions. For sure selling is really important then, but selling permeates all aspects of starting and building a business.

You need to sell when you’re asking friends and fun friends and family for a money or a loan. You need to sell to your bank if you need a bank loan.

You need to sell to service providers, especially if you’re hoping to barter services early on when funds are tight or totally non-existent.

You need to sell to those first employees to take a chance on the opportunity to be part of your growing idea before it really takes off. Because for them there’s a risk they may not end up getting paid or have to look for a new job if your business craters.

Listen to my interview with Melissa Kehl, the CEO of Rieke Interiors. She talks about how she had a huge cashflow problem at one point. Her business was seriously in need of money. And she owed a lot of money to her suppliers. And instead, she sold to them a package where they would all reduce the amount owed and accept payment from her over time. Now that I think requires some serious selling!

And of course, there’s the big one: you need to convince your customers that they need your products or your services. And that your offer is definitely worth paying for when there are usually lots of alternatives, some of which might even be less expensive than yours or better known.

It said that to be a great salesperson, you need three things:  1) you need a great product or service; 2) you need a great company that sells it; and 3) you need to believe in yourself.

And as a startup entrepreneur, you may have a great product or service. Or maybe it’s just a great light bulb idea. 

But ultimately, at the very beginning, you have only one of those things: yourself. Just you. No one knows your product, yet they don’t know your company. So you have only you and your belief in yourself. And that’s doubly true, I think, for companies offering a service.

And that’s why it’s so sad that a lot of businesses fail. Ultimately, the founder /owner ends up losing faith in himself or herself.

So what do you do if you find yourself doubting yourself and your abilities?

There are lots of frameworks out there.  There’s lots of self help books, inspirational TED talks.  You’ll find plenty of them if you go looking for them.

I personally love the framework set out by an organization called SoulSalt. And I’m unabashedly lifting some things from a framework that they have out there on their website. And I would encourage any of you who struggle with self doubt to visit the site & check out some of their tools & resources.

Their framework has five steps to improve our belief in ourselves.

1. Work on your strengths, not your weaknesses.  Make a list of what your strengths are. Most of us already know what some of those are. But it helps to write them down so you can see them in black and white (or even better, in an energizing color!).

But if you’re not sure, there are tools for that, too. There’s the StrengthsFinder 2.0 quiz. It’s kind of fun to do.

Or, try making a list of things people have told us over the years that we’re good at. Make a list of your past accomplishments that have made you proudest or brought you the most satisfaction. I bet you’ll start to see patterns.

Then work on those strengths. Identify what you’re not as good at that needs doing in your business, and brainstorm about ways to help find with those. It could be a partner or a mentor, an outsourced service provider, an intern, or a virtual assistant, or a MeetUp group.

2. Be your own coach.  To do that, you have to first stop being judgmental with yourself (easier said than done for many of us, especially we women, I think).

Then write out the things about your business that you’re not very happy with at the moment, or are not satisfied with.  Try to come up with little plans to improve each of those aspects.

3. Embrace who you are. Stop trying to be someone who’s not you.  Look at whether or not you’re trying to meet other people’s expectations. Focus on your core values. Write down a list of things that are really important to you.

Then start to be more observant of your own thoughts and emotions, try journaling. Start noticing where there is a conflict or stress between how you feel and spend your time versus what’s really important to you on that list of core values.

4. Continually tell yourself you can do it. Yes, I know this sounds a bit Pollyanna-ish. Be your own cheerleader, that sort of thing. But the fact of the matter is, it’s not just wishful thinking. Because if you believe, you can do it. You tell yourself you can do it.

Doing this changes the way you see the world and yourself. A lot of us — not just we entrepreneurs — subtly sabotage ourselves by listening to and even ruminating on that downward cycle of thinking. That reinforces that self-doubt and those negative thoughts. You need to stop feeding those thoughts!  Do not feed that troll!

You can either see endless possibilities or insurmountable obstacles. And it’s up to you to choose which way you want to frame the issues.

5. Get Comfortable with being uncomfortable. This is the last step in SoulSalt’s framework, and it’s my favorite one.

I think a lot of first time entrepreneurs get stuck here as well. It’s awfully easy for us human beings who don’t like change all that much to do the same things you did yesterday or last week. You tell yourself that you’ll get to that thing, or that big, hairy goal tomorrow, or next week, or the week after. And somehow a month or more slips away.

Another my past guests said it in another way: If you’re comfortable, you are not taking enough risks. I think that’s true of entrepreneurs. I think that’s true, frankly, of all of us who want personal growth. So you need to keep experimenting and trying things.

One idea that of my own that I didn’t see this on the SoulSalt site is to list of all the things that you see other companies doing to promote their products or grow their business.

And that can be all kinds of things. Just start looking around, reading the news, watching the LinkedIn and Twitter and YouTube feeds.

Maybe it’s making a video promotion, or doing live Instagram, or YouTube events, posting goofy stuff on social media, holding contests, partnering with other businesses, or doing press releases. There’s so many different things that businesses do.

So make a list of them. And ask yourself if any of these just might possibly help your business? Which ones of those are do-able for you? And if so, how would you go about doing that?

As entrepreneurs you know, we love brainstorming with others about ideas, but we often suddenly shoot down and sabotage our own thoughts. But why? Why do we do that? The world is truly full of endless possibilities.

It’s said that entrepreneurship is a journey, it’s not a destination, and I firmly believe it.

So embrace that journey. Have fun with it, try goofy things, try weird things, go out on a limb.

Give yourself permission every day to do the virtual equivalent of skydiving. You know, jump out without a safety net. As one of my guests said recently, “Unleash yourself!”

For more ideas on how to restore your faith in yourself — or maybe build it if you never truly had it in the first place — I really do recommend checking out SoulSalt – they have lots of great, practical suggestions.

What have you found helpful? I’d love to hear your thoughts and suggestions!

Today’s blog comes courtesy of Rene Brown, author of Daring Greatly, which is a book that I absolutely loved.

She is somebody I really respect and admire. She says what she thinks and she doesn’t pull any punches.

Her tip for this week is get better at asking for help.

Here’s the quote that I lifted from Daring Greatly:

“Somehow we’ve come to equate success with not needing anyone. Many of us are willing to extend a helping hand. But we’re very reluctant to reach out for help when we need it ourselves. It’s as if we’ve divided the world into those who offer help, and those who need help. And the truth is that we are both.”

I picked this quote because I came from a farming community where you, you were wired up to get things done yourself, figure it out. There was a lot of pride in being self-sufficient — maybe a holdover from the pioneer days.

But in today’s world, I think the successful entrepreneur is someone who reaches out and finds that support network isn’t afraid to say I don’t know how to do this or I’m not sure how and reaches out.

, I want to return to a theme we’ve talked about on this show a couple of times in the past – and that is the disparity in self-confidence, or self-promotion,  or whatever you want to call it – between men & women entrepreneurs. 

I was thinking about this as I once again got ghosted by a female entrepreneur.  For the record, I have only anecdotal information.  But in the now 3 + years that I’ve been doing this show, I’ve never been ghosted in a conversation about appearing on the show or been ghosted in any way by ANY male entrepreneurs.  Not once. 

But I have been several times by women entrepreneurs.  And I’ve had lots of conversations with potential women guests where it’s clear they are very reluctant to agree to be a guest on the show.  We have an introductory chat, but we never manage to get the interview on the calendar.  Either they don’t get back to me, or they schedule but cancel at the last minute.  Or they say they’re just too busy.  Too busy that you can’t talk to the media for a few minutes?  Too busy for free publicity or the chance – for free – to showcase your business & your story??

So what’s going on here?  Clearly, women either lack confidence, or somehow fear or are apprehensive about the spotlight. 

A recent study by Women of Influence out of Canada suggests that at least part of the problem is the underlying fear of negative consequences. 

The study documented that this really IS a thing.  They even have given it a name:  The Tall Poppy Syndrome.  The term is Australian, and referred to anyone who stood out too much – the idea being that you need a nice, uniform field of poppies, and any poppy that gets too tall needs to be cut down.  It’s since been used by women advocates to refer to women who get cut down. 

In their Tall Poppy Syndrome study, more than 87 % of high-performing women felt that their successes had been undermined in the workplace.  NOTE:   this study ONLY looked at undermining in the workplace – it did NOT look at all the other places that women feel undermined for their success – by their spouse, their family members, their neighbors, people at their church, their friends, etc.  And as someone who has personally experience this, I personally believe THIS undercutting is even more painful and memorable.

Taken all together, it’s like putting your fingers on a hot stove.  You do it a few times, you feel intense shame and pain, and you stop trying to stand out.  I have found myself on a number of occasions downplaying a success because I was trying not to be a Tall Poppy. 

Interestingly – and again, this certainly jives with my own experiences – men and women were found in the study to be equally guilty of the undercutting. 

The most common reasons high-performing women were cut down?  (1) jealousy (2) sexual/gender stereotypes and (3) feelings of insecurity & inadequacy on the part of the person doing the cutting down.  As you can see, most of the cutting down is more about the person DOING the cutting than about the high-achiever, but that doesn’t make the cutting down any less painful. 

This is really a tough one to overcome.  How do you fix someone else’s jealousy or feelings of inadequacy?  I guess one thing that can be done is for managers to receive more awareness training of ways they unwittingly (or even wittingly) permit or tolerate, in the hopes of slowly changing our culture. 

The gender/sexual stereotypes are slowly changing over time, but this, too, is difficult.  As the recent national debate in the U.S. about abortion rages, it’s clear that there is still a very large segment of the population who believe women should have less rights, do not have the right to control their bodies,

People can go on & on about right to life, etc., but it’s pretty hard not to take that discussion towards its ultimate end — that somehow women are less – at least in the business world.  The implication is that women are intended to bear & raise children – hopefully the next generation of women to do more child-raising, and men to rule the world, which is the rightful order of the world, apparently for many.

What can we women do on a personal level to combat some of that pain, that knee-jerk reaction to lay low, to not make waves? 

I find a great blog on a site called Refinery29.  I have no idea why it’s called that, but the blog is called  “I Tried 30 Different things to Boost My Confidence, & Here’s What Worked.”  The author polled her women friends colleagues to ask them for their best tips for things that had helped them boost their confidence. 

It’s a wild list, with everything from naked yoga to daily affirmations to stand up comedy and skydiving.  You can try things on this list, or for funsies, you can even poll your own friends & colleagues & come up with your own list to try. 

The key is to keep trying different things until you find things that work for YOU.  And interesteingly – but not surprisingly – the list this blogger came up with – and probably this will be true for any list you come up with yourself – really boils down to 2 things:  (1) continue to do things that are out of your comfort zone, and (2) do things to better identify & control negative thought patterns. 

Doing things out of your comfort zone builds confidence.  With every activity you do, you gain the confidence that you CAN do it – you DID do it, and you lived to tell about it.  You don’t need to be the next Second City improv star to gain lots of self-confidence taking an improv class. 

Second, there is no question that the cycle of negative thoughts often swirl around in our brains without our even thinking it.  And thinking then becomes reality.  Furthermore, it really is possible to change your thinking by catching yourself with those thoughts, and substituting them for something more positive. 

I tried a bunch of the things on this list.  The blogger found – as did I – that daily affirmations help.  For me, I have these ridiculous post-it notes all over my office and around the house, and I change them out as they fall off.  That way, I remind myself throughout the day to think more positive thoughts about life and myself. 

Another one that worked for me that was not on the Refinery 29 list, but came from another friend: simply smile more often.  A customer service rep is driving you crazy?  Smile.  Find the humor in it.  You read something in the news that upsets you?  Turn it off and find a funny cartoon and smile. 

Try it – this might work for you, too!

I’ve seen there is often a disconnect between what you as entrepreneur want from the business and the risks you are willing to take. 

And this isn’t just a theoretical disconnect.  I’d argue you can’t develop meaningful goals for your business without reconciling this conflict.

Let’s deconstruct that, and then talk about a couple of examples. 

First, it is CRITICAL that you are clear about what you want from the business.  Income, yes – but how much?  Is it more important for you to make a comfortable wage, or are hoping to make a LOT of money growing or selling your business? 

How important for you is to to change people’s lives?  Or give back to your community? Or simple make something cool? Is it because you like building things?  Fixing a problem?  Making customers smile?

WHY do you want to create a business?  Or WHY EXACTLY did you create the one you have?   Some people tell me, “Oh, I don’t know.  I just knew I didn’t want to work for “the man” (or “the woman” – but that is not enough clarity to move forward with a successful business.   I always admire those people who seem very clear on their “why.”  Some people, I suspect – maybe because I’m a little jealous! – clearly state why they started and are running the business they are, and I’m not always sure if it’s the truth or just that they’ve perfected a good story line.  In any case, there are clearly some of you out there who really ARE CLEAR about why you started and are trying to grow your business every day.  You ARE indeed lucky!

Many of us truly aren’t very clear about WHY we started the business we did, or why we work so hard at it. 

If you’re struggling with your “why,” I have recommended in the past and wholeheartedly recommend again Simon Sinek’s “Start with why,” and his followup book, “find your why.” 

There are lots of other exercises out there on the internet, some of the best of which are linked here on my website  But I think Sinek’s books are the best – it is difficult to see ourselves clearly sometimes, and what I like about his books is that they take you through some of the mental – and emotional — preparation that’s needed to see ourselves and our motivations more clearly. 

OK, so that’s what we are entrepreneurs WANT from our business.  Now let’s talk about the other side:  what risks are you willing to take? 

The risks you take can take lots of forms.  Most people probably focus on the financial aspects.  And that’s a pretty important one.  Are you willing to mortgage your home or take on a second mortgage?  Are you willing to spend down all your savings?  Do you have enough cash saved up to last you for several months or even a couple of years? Are you willing to tap into your IRA?  Are you willing to take out a loan or borrow from friends or family? 

But it’s not just money.  Are you willing to move out of your comfort zone – sometimes frequently?  Receive criticism? Have friends and family think you’re crazy?  Spend long, long hours away from your family? Take risks when you have no idea whether you’re making the right decision? 

Whatever the risks in your situation, make sure you’ve VERY explicitly discussed these with your family, as well as your business partners.  As we talked about last week, all too often, the costs are greater than we anticipate, and that can leave you feeling stressed, overworked, and sometimes not even enjoying the process, but feeling trapped because you’ve come so far to throw it all away. 

I’ve seen quite a number of would-be entrepreneurs who can’t move forward, because they can’t reconcile this disconnect between what they want in a business and the risks they are willing to take.  A woman who wanted the security of a franchise restaurant model, but dreamed of creating new, interesting dishes with her daughter.  Another women who wanted to open a high-end daycare, but unwilling to mortgage her home to finance the facility investment she would need to make.  A physician with a novel medical device who insisted on being the CEO, but just couldn’t accept taking less than his current salary as a doctor with a successful practice.  Another man with his grandmother’s cupcake recipe, but who couldn’t make any decisions about how to create a business around this. 

As we talked about last week, the answers to these questions will drive a lot of your daily decisions – how you spend your time, who you hire and what you delegate to them, and how you invest in the business, and even were you look for funding and how much you are seeking. 

And as I said earlier, it is not possible to make meaningful goals without being clear about your tradeoff between what you want from your business and what you are willing to risk. 

You may find the risks are greater than anticipated, and so your goals may change once you realize that – and that’s OK.  It’s a normal part of the journey.

But your path will be much clearer if you’ve got a good handle on what you what from your business, and the risks you’re willing to take from the very start. 

Here’s something that I tell clients who are starting their businesses to think carefully about.   

Lots of entreperneurs – as their business is growing – don’t necessarily want to expand and scale their business as quickly as possible.  If you enjoy the interactions with your customers, being personally involved in the day to day operations of the business, and connecting with your local community, you  might lose much of that if you expand quickly. 

What I always advise my clients is to “Begin with the end in mind.”  I can’t take credit for that expression – it came from Steven Covey.  Although Covey wasn’t specifically talking about starting a business, it applies equally here.   In my experience, Many entrepreneurs don’t think in terms of what they want their exit from the business to look like, until the moment is nearly upon them.  And that’s generally not a good thing.

Because many of your daily decisions about your business affect your ability to successfully grow and manage and yes, exit your business, when the time comes.  I can think of a few examples, but if you think this through for your own business, you’ll see what I mean. 

Let’s take something as basic as how and where you find funding.  Let’s say your goal is to successfully sell your business or go IPO.  In that case, you may want to aggressively look for external funding from angel investors, family offices, and even VCs.  That will give you the cash to (ideally at least!) rapidly expand your business, showing amazing fast growth and producing the multiples that might lead to a lucrative exit. 

But the truth is that many entrepreneurs LOVE their business.  Many, many are the entrepreneurs who believe they want to scale their business and grow rapidly.  That will make external investors happy.  And if your goal is to make a bunch of money and move onto to your next venture or retire early, that’s great.  But all too often, the entrepreneur finds that it doesn’t make him or her very happy.  It often quickly pushes the entrepreneur founder into roles that are not nearly as much fun, are not very connected to the day to day hustle and bustle of production and interacting with customers.  Suddenly, the entrepreneur spends more time hiring people, delegating things to others, and focusing on policies and procedures and administrative headaches.  Remember, the goal for the founder is to make himself or herself essentially replaceable, so that the business can continue running in the future without them at the helm.  That’s the cold reality – if your business is acquired by a strategic, they may want you around for a short transition, but are often eager to start integrating the business into their own company.  If you go IPO, unless you are also a very effective manager and leader, your board or shareholders will often start pushing you out the door. 

The truth is that many people who are great at starting a business and even running a small business aren’t very good at scaling the business and running a larger enterprise.  And I believe – from the many entnrepreneurs I’ve worked with – that many of them have such a hard time extracting themselves from their business – their BABY – that it gets in the way of the scaling that is needed for rapid growth. 

I love Elaine’s clarity about Luft Balloons – she realizes that it is her baby, and that she not only makes good money for herself and for her team, with whom she is close – but gives her a great deal of personal satisfaction.   I suppose some people (rather sneeringly, I think) call this a “lifestyle business.”  I think we need to come up with a better name that gives this option the respect it deserves.  There is nothing magical about “scaling” nor is there anything AT ALL wrong with creating a thriving business that you, the founder, are in the middle of and want to stay in the middle of for a long time – maybe a very long time.  And there’s another way the end game affects your daily decisions – if you want to stay small, you might hire generalists and people who thrive in a small, family-like environment.  But if you want to scale, you will probably want different people – hard-chargers, maybe, or people with experience managing larger departments, probably people with more specialized expertise. 

I think the hard part is that many entrepreneurs don’t always know what they want when they start.  Many say they want to scale their business quickly (maybe because we’ve all been a bit brainwashed by the tech industry talking about huge IPO numbers), but when push comes to shove, that isn’t really want they find they really want.  But it sure helps if you have done some real soul-searching ahead of time or at least early on.  The world is full of founders who thought they wanted to scale and brought in external investors, only to find they have lost a lot of control over how the business grows.  Or, they’ve actually hired the wrong people. 

Take the time to step back and answer as honestly as you can, “What makes me happy?  What are the kinds of activities that I’m really good at and enjoy the most?” 

And design your business around that.  Because if it’s not fun, what’s the point?