What type of entrepreneur are you?

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When I set out to work for myself just a year out of college, I didn’t know what I was doing. I just knew that I had some skills (writing, communicating, helping people and ideas get seen, known and heard), and I wanted to shape a career around those skills.

Last night, I was nerding out on the American Express 2018 State of Women-owned Businesses report, and it gave language to something I’ve experienced but hadn’t quite articulated that way.

The report talks about three kinds of entrepreneurs: NECESSITY entrepreneurs (need to start a business for income), OPPORTUNITY entrepreneurs (target a market opportunity) and FLEXIBILITY entrepreneurs (want to control when and where they work).

We hear a lot about the flexibility entrepreneurs in these internet streets, but not so much about the other two types.

When I started working for myself, I think I was a combination of all three. I needed to make a job. I saw an opportunity: many nonprofits didn’t have the resources to bring on full-time staff, but they needed good writers to get their work out into the world. I also wanted the flexibility of being able to work from wherever so that I could finally get out of my hometown and see the world.⠀⠀⠀⠀⠀

As I’ve gone on to have a career as an attorney and education policy consultant, knowing how to work for myself has been a tool in my back pocket that I can pull out whenever necessity, opportunity or a desire for flexibility comes up.

I love that.

It makes me feel safe. I can choose to have the stability of work and still be able to take on consulting clients as capacity allows.⠀⠀

It makes it easier to say no. It keeps me from staying in situations that aren’t a great fit. I can spot opportunities in my community and have the business tools to do something about it. And there’s effectively no ceiling for my income.

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Which kind of entrepreneur are you? Necessity, opportunity or flexibility? A combo of all three? Let me know in the comments or shoot me a message. Leave a comment and let me know.

What's your "break the glass" strategy?

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If you needed to make (not find) work for yourself, how would you do it?

When I first started consulting, I was just out of college and wanted to chart a path of my own choosing. I was so committed to my vision of using my writing and media skills to support nonprofits that I was thrilled to waitress at Olive Garden at night while building my book of consulting business by day.

The dream didn’t always look pretty, but it was mine.

Since landing my first client 15 years ago, I've consulted for a national health advocacy organization, a social justice magazine, music artists, a large-scale $2.8 billion community development initiative and many more. Consulting has provided an opportunity to serve a diverse roster of clients (turned friends), and it has been a valuable tool and safety net throughout my career.

Consulting was a tool to generate more income while earning my master’s degree and my law degree.

Consulting has been a tool that I've leaned on most recently when I quickly realized that I needed more control over when and I how I worked now that I'm raising two tiny humans.

Consulting has even made me a better employee as I've gotten more comfortable taking ownership of projects and leading them as if they're mini-businesses.

Here's what so powerful:

When you have the business skills to create work for yourself, you can walk with a certain confidence and freedom knowing that you’ve got YOU. Having the skills to pitch clients, generate business, and market, sell and deliver your professional brilliance gives you options.


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Here's what it means to Own Your Expertise.

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You do not have to quit your job and move to Bali to be entrepreneurial and live your best life.

Somewhere along the way, the entrepreneurship craze has brought on quite a bit of 9 to 5 shame.

And it's a shame, especially because so much growth and preparation for entrepreneurship can take place on your job if you're open to it.

The leap-and-figure-it-out approach may work for some, but not for most of my clients. And it may not make sense for you if you're anything like them:

You're the colleague people come to when things need to be executed with excellence.

You're thriving professionally and in a good space.

But for all that you've accomplished, sometimes you feel trapped.

You've mastered the job context, but all of your years of education never taught you how to thrive on your own.

In a sense, you feel both badass and boxed in.

You're under no illusion that hustling on your 9-to-5 is sustainable or the path to reaching your financial goals. But you're not trying to quit your job and move to Bali.

You have college tuition to save for, aging parents to care for, a mortgage, a self-care budget and good health benefits that you actually use.

When you see these coaches and gurus pop up in your newsfeed promising to show you the way to six figures in 60 days, you are unimpressed and unmoved.

They get the side eye because you know the blood, sweat, tears it took to earn every comma in your bank account.

I believe there can be a third way for women like you who want to continue to thrive in their jobs now and equip themselves to thrive on their own when they are ready.

You can do both.

You can become an even greater asset to your employer by being entrepreneurial and leveling up your personal brand.

You can make a greater contribution as a leading thinker and fresh voice in your field.

You can generate extra income from speaking, consulting or publishing without risking it all and burning the candle at both ends.

You can become a brand now and make a strategic shift into entrepreneurship when you're ready.

That's what it means to own your expertise.


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Marketing at the "Speed of Trust"


I couldn’t, for the life of me, understand the marketing practices some people use these days.

Then it dawned on me as I was talking to my husband the other day: many of the folks operating online businesses have likely never operated business offline. They act as if they're marketing to clicks and algorithms instead of actual people.

Customers are living breathing humans with work commitments, screaming kids, annoying coworkers, fixed paydays, depression and anxiety they're trying to keep at bay. They’re also smart and not fooled by disingenuous scarcity tactics, false urgency and shouting.

To be clear, I’m not saying these marketing tactics don’t work. Sales psychology is real and effective.

But, as I told my last group coaching cohort of aspiring women entrepreneurs, the real question is: Do these tactics attract the kind of people you want to work with?

I don’t want people to feel rushed or pressured into making a decision. My people are smart women who make thoughtful choices, and they lead with both head and heart. They want to reminded, but not bugged. They want to be informed, but not bludgeoned. They want to be trusted to make the right decision for themselves and not coerced, only to regret it later. I want to attract more of those people and not just grow for the sake of it.

Trust me, I don’t always get it right. I’ve tried on different marketing advice, and quickly took them off when they didn’t fit.

I’m fully aware that my business growth may be slower, but I keep my eyes on my own paper. As adrienne maree brown (@adriennemareebrown) says in her book Emergent Strategy: I choose to “move at the speed of trust." (quoting Mervyn Marcado’s remix of Stephen Covey’s concept)

I believe that in all things—yes, even in business—we can operate from a generative place. We can call people into the best versions of themselves instead of playing to their insecurities. We can write marketing copy that helps people feel seen and heard instead of poking at their wounds.

Honesty. Clarity. Space. Time. Respect. Honor. Joy. Doing good work that helps people. That’s my kind of business.

Originally published on Instagram. If you'd like to connect with me there, I'm @titilayo.


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Working for yourself isn't easy, but it doesn't have to be so complicated.

Last week, I was chatting with someone who was feeling a tad bit overwhelmed by her business to-do list. I asked permission to share a reframe that might help, and she welcomed it.

My advice was really a question for her to consider: Are you even sure the things on your to-do list are things you should be doing?

It turned out that she, like so many of us, had fallen into the sunken place of trying to do all the things the gurus and experts said she should do--courses and funnels and blogging and social media and fancy websites and, and, and.

We can be inspired by the way others have done business, but their successes don't mean that their way is the only way. And something may be the right tactic but just not the right time for where you are in the life cycle of your business.

If we aren't careful, we'll get to a place where we can't hear our own voices in the midst of all the noise.

I made something for her and for you. My new checklist distills the process of getting your first (or fiftieth) client down to six essential steps that you can shape around your particular preferences and goals.

Working for yourself isn't easy, but it doesn't have to be so complicated.

Originally published on Instagram. If you'd like to connect with me there, I'm @titilayo.


Get my 3-Month Consulting Launch Checklist and discover must-do action steps and mindset tips for landing your first consulting client.

The Beyoncé of Things: A Reminder to Put in the Work

Last week something happened that proves a principle I'm constantly hammering home when I work with aspiring women entrepreneurs.

As you may know, in addition to teaching business skills, I have a consulting practice of my own advising companies on project rollouts and collaborating with thought leaders to write books, research studies, reports, case studies, etc.

So, I don’t just teach this, I live this.

I recently started the first of two projects for a client that will span the next 18 months.

This now means I’m booked out for the next year and a half.

And I don’t have a website for my consulting practice.

Or a business card.

Or a business name that I’m happy with.

And I don't market my consulting services on social media.

Every consulting client that I have gotten over the past 15 years has been through a referral from a former colleague or client.

Here’s how things have worked for me: I’ve shown up. I’ve done my work. People have presumably appreciated what I've brought to the table and have enjoyed working with me. Then the next time they or a friend are working on a project that could use my skills, they think of me.

That, my friends, is the big bold marketing strategy I have for my own consulting business.

Which brings me to a point I want to make about Beyoncé (I mean, isn't she always the point?).

#BeyChella wasn’t just a display of performance genius, it was the inevitable fruit of a woman and a team that have put in the work.

Let's talk about that part.

Aspiring entrepreneurs get more than enough advice on branding, websites, etc. that often leave them feeling like they're less than because they don't have a fancy storefront yet.

Are these things important? Yes, at a certain point (hint: not when you’re first starting). Are they essential? No. Because if you don’t have the substance to back all of that up, your on stage performance will fall short.

You're doing the work. You've developed mastery in your area of expertise. Keep pushing, showing up and serving, and then reinvest in your business with all of the fancy branding when you're ready. Or don't.

Here’s my mantra, and feel free to make it yours: Mastery first. Marketing second.

This isn’t about creating 15 minutes of business fame or just looking the part. It’s about building and launching a sustainable venture that can support you and speak for you for years to come.

Your work is your brand. Your reputation and relationships are your currency.

Your website? Your business cards? Your lead magnets? Those are all tools. And they’re meaningless without a solid foundation of you putting in the work.

So look at your work for a second today and think, how can I be the Beyoncé of things?

Then slay.

It's OK to Want More

This morning, a post from Kate Northrup landed in my inbox, and she was writing about how desire and gratitude are not mutually exclusive.

It reminded me of a common roadblock that I often see women come up against when they are considering stepping out on their own. They often wrestle with thoughts like, “So many people don’t have jobs, shouldn’t I just be grateful for what I have? Am I greedy to want more...more time? more money? more freedom? more flexibility? Isn’t this good enough?”

Truthfully, you are the only one who can answer these questions for yourself.

But I'm here to tell you that if you’re asking these questions, then your inner knowing is very likely calling you to something greater.

In a recent Facebook post, I talked about how it’s OK to want more. It’s OK to want less. You have permission to evolve.

But many of us worry about what this evolution might mean—for our bosses, our romantic partners, our families, our bank accounts, our friendships, established power dynamics, and, and, and.

All of these things are very real fears.

Change is always threatening.

If nothing else, it threatens the status quo and leaves you and everyone else trying to figure out where you and they fit into the new paradigm.

Change occurs when there’s a shift in your worldview and it almost always disrupts the views others have of you.

If you dare to want more and actually go after it, others may think you're not staying in your place. You may challenge others’ sense of dominance. You may rattle someone’s sense of security.

I’m not here to tell you that morphing into the next level of you will be easy. I’m here to say that in spite of the risks and real fears, it’s your only choice if you ever want to quiet that nagging voice inside of you that wants more.

The reality of our work world is that even in the best dream job scenario, women especially are forced to choose between nourishing themselves and growing their careers. And most of us are the kinds of women who don’t just show up at work—we crush it and do so making a fraction of the salary that our less qualified counterparts earn, and our health, relationships and well-being suffer because of it.

This is why I’m so passionate about helping you own your expertise.

It’s not just about work.

Owning your expertise is personal. Conquering self-doubt and getting comfortable with communicating your skills to clients has a spillover effect on your relationships, health and finances. Knowing your worth and unapologetically showing up starts with your career, and then it becomes your method of operation in more and more areas of your life.

Owning your expertise is political. It gives you the option of leaning out of a system that was not designed for you to thrive, opting out of career paradigms that are riddled with inequalities, and leaning into a career of your own making.

Owning your expertise is financial. The majority of full-time freelancers are women, and in most countries freelancers earn more the full-time workers. Women are more likely to be the primary caregivers in a family, and they are increasingly becoming primary breadwinners. When we work and earn on our own terms, we have the potential to make more which makes us able to do more for ourselves, our families and our communities.

Owning your expertise is powerful. Women who work for themselves are often better positioned to champion diversity, whereas doing so within existing organizational structures often carries a hidden penalty. A Harvard Business Review study found that for women of color especially, the emotional labor of championing diversity in the workplace can actually take a professional toll and has even been shown to carry a professional stigma. When you work for yourself, you have the option of subcontracting or hiring consultants and employees in a way that matches your commitments to equity and doesn’t undercut your potential for career progression.

Owning your expertise is inspirational. Visibly leveling up your career can be an act of service that calls out the greatness in others. As Marianne Williamson says, "When we shine we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others."

Owning your expertise is radical. Many of us face systems that have historically owned our expertise, both figuratively and literally. To take a stand and own your expertise against this historical backdrop and the ongoing constructs that perpetuate inequality is a radical act and an act of self-care. As the inimitable Audre Lorde famously said, “Caring for myself is not self-indulgence, it is self-preservation, and that is an act of political warfare.”

Getting to a place where you're comfortable, confident and competent enough to step out on your own is a journey.

I've been there, and I'm here to help you through it.