Making Career Choices that Align With Your Values and Why I Said Farewell to Big Law

In today’s episode of the Own Your Expertise Show, I’m sharing about the recent decision I made to shift out of working for big law and explore other exciting ways to support businesses with my legal skills.

Also, tune in to hear about how to get one of the limited private coaching spots I’m offering between now and the end of the year. As I mention in the episode, I likely won’t be doing more one-on-one work again until at least summer 2020, so if you’d like my support reaching your entrepreneurial goals, listen in and head over to the private coaching page to learn more.

Lastly, if you’ve also been considering making the leap into entrepreneurship, tune in as I describe the modules in Before You Leap, my step-by-step mini course that walks you through the exact process I’ve used and I’ve coached others through when making the transition from employee to entrepreneur.

Let’s go to the show.

P.S. Enter the code “freedom” to get 30% off Before You Leap (only 10 coupons available and they expire in a few days).


  • The thinking behind my recent decision to shift away from practicing in big law

  • How the most adorable “last day” party my kids threw for me took a painful turn

  • What I’m up to now and what’s on the horizon for me personally and at Own Your Expertise

  • The difference between running to entrepreneurship and running away from your job

  • How the Own Your Expertise team is growing and my new private coaching offerings

  • The 5 steps my new mini course Before You Leap walks you through to prepare you for the transition from employee to entrepreneur


5 Mistakes to Avoid When You're Considering Taking the Leap Into Entrepreneurship

Wondering if now is the right time to take the leap into entrepreneurship?

Listen for mistakes to avoid and tips for dealing with these common roadblocks, then be sure to check out our NEW Before You Leap Mini Course.

We're in a moment right now where it seems like everyone is an entrepreneur or considering becoming one. Stepping out on your own has become the sexy thing to do.

But I think it's really important heed the wisdom of our elders and “count the cost” of exactly what that transition from employee to entrepreneur might look like and be more thoughtful and strategic.

Many of us are at points in our careers where we have responsibilities: a mortgage or two, student loans, children, caring for yourself and nurturing other loved ones.

From the many different places most of us mid-career professionals sit, we don't have the luxury of just leaping and figuring it out later.

That’s just not a thing in our world.

So it's really critical that we get strategic, be thoughtful, reel that passion back a little bit, slow down and truly consider exactly what this transition looks like.

To help us out, I'm going to share five common mistakes that I often see aspiring entrepreneurs make and how to avoid them.

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Mistake #1: Forgetting how dope you are

One of the things I'm always so surprised to hear women say when they are considering stepping out on their own is, “What could I possibly have to offer to the market that might be a value? What would people even pay me to do?”

This, even though they are often very well paid in their corporate jobs doing work that people clearly find valuable.

It’s tricky.

When we’re too close to our accomplishments and talents, it can be hard to see them. We’re often really critical of ourselves and don't really see often the special sauce that we bring to the table.

And don’t get me started on the socialization that often results in us shrinking back from speaking up and owning our skills.

Try this: In addition to doing your own self assessment, consider tapping into your network of friends and colleagues who really know you well. People who love you and who've known you over time can often give insights into exactly what it is that you bring to the table that others don’t have.

Mistake #2: Focusing on the “what” MORE THAN THE “why”

The second mistake I see people make is starting out too focused on the “what” instead of the “why.” New entrepreneurs often get annoyed and fight me on this point at first. Then, almost without fail, they circle back later and realize it’s sound advice.

People get so in the weeds about the tech, website, logo, business name, branding, etc., at which point starting a business can get incredibly overwhelming. When you're first starting, try to resist diving headfirst into the “whats” of business.

Sustainable businesses are first built on a solid why.

One of my favorite books is by Simon Sinek: Start With Why. His premise, after having studied several businesses, organizations, leadership structures, military science, etc. is that the way that businesses really succeed and make a lasting impact are the ones that start with why and not the what.

In the book, he gives the example of Apple. Have you noticed their billboards and commercials don't really talk about the specs and the tech of their computers until they first hook you in with a story that gives you an experience of why it even matters? They lead with how that technology is going to make you feel, and then they follow with the tech.

Try this: So think about why in two ways: think about why you are interested in entrepreneurship. Are you a necessity entrepreneur (you need to move forward in entrepreneurship because of your financial circumstances). Are you an opportunity entrepreneur (you see a gap in the market and you want to fill it)? Or are you a flexibility entrepreneur (you want to have the freedom to work and live on your own terms)?

Really get clear on why you're moving forward in this direction so that you can stay grounded in your reasons and use them as a compass to guide some of your decisions moving forward.

Of course, this applies to your business directly as you start crafting your offers and figuring out what your business will be. You really want to get clear on the why for your businesses and make sure that you're communicating not just what you offer, but the story and meaning behind why that service is important to the people that you serve.

Mistake #3: Reacting instead of creating

The third mistake that I see people make when they're considering leaving their jobs and working for themselves is coming from a reactionary perspective instead of a generative and creative perspective.

I posted a statement on Instagram recently that seemed to really resonated with a lot of people: Entrepreneurship is not a cure for job dissatisfaction.

It’s true. It may lead to and be a tool of personal fulfillment, but it can’t only be that. Entrepreneurship isn’t just a thing to do when you don’t like your job.

Job discomfort can certainly nudge us and get us out there faster with fire in our bellies and under our butts. But that alone is not a reason to go into entrepreneurship—at least it can’t be the only one. If you don't have a solid business model that meets a need in the market, you won't be in business for a long.

Try this: Consider coming from a generative place and a creative place instead of just a reactionary place where you're mostly leaping into entrepreneurship because you hate your current situation. Assess where you are right now and develop an intentional plan and goals for exactly what entrepreneurship is going to create and generate for you and for others.

Mistake #4: Not knowing your numbers

The fourth mistake that I see people make, especially those who might be like me—liberal arts, English major types—is avoiding looking at the numbers. Math has never been my thing, and maybe it hasn’t been yours. But as business owners it just has to become our thing.

Try this: Friend, you need to run those numbers. You really need to know exactly what your revenue goal should be and how you're going to get there. A lot of times people think their business should be aiming for their work salary to make an even exchange.

Not so.

There's so many other factors, expenses (and write-offs), investments and more that come into play when you're a business owner that aren't really in the picture when you are an employee. The Income Clarity Spreadsheet inside Before You Leap is a tool that I've created to help you crunch your own numbers and think through your revenue goals.

Mistake #5: Going it alone

Entrepreneurship can be a lonely endeavor and a lot of times we don't have others immediately around us that are doing it. On the one hand, it feels like entrepreneurship is like in the zeitgeist and everyone is doing it, then we turn to our immediate local communities and it can feel a little lonely.

To the extent that you can, build in time for community. Seek out connections. Particularly look for people that are what Lacey Phillips of To Be Magnetic calls “expanders”— people who, as much as possible, reflect similar things about you but are doing what you want to do in the future. From a neural pathways perspective, seeing expanders starts to train your brain to think that what you’re going after is actually possible for you.

That's why representation matters. That's why diversity matters. That's why images matter. That’s why visibility matters.

It matters for you, personally, but it also matters for others who will look at you and say, “She did it, and now it’s possible for me, too.”

Try this: Research industry conferences that are related to your field. Join relevant Facebook groups and deepen those connections offline. You can also identify “imaginary” mentors and friends. If you admire a business owner from afar, research and reverse engineer their interests. Learn from the breadcrumbs they’ve left along the way.

Join my NEW Self-Paced Mini Course
Before You Leap
Available for Early Enrollment Now

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In this mini course, you’ll work through the exact questions and prompts I’ve used to coach myself and others through making the transition into entrepreneurship.

Go from “maybe-preneur” to absolutely sure about whether or not entrepreneurship is the right step for you.

Before You Leap is an easy-to-digest, practical course that you can get through in about an hour. Inside you’ll find:

  • Step-by-step lessons that walk you through: 

    • How to assess your most marketable skills 

    • How to determine what type of entrepreneur you are and the steps you should take (and avoid) most immediately

    • How to set clear goals and intentions for your shift into entrepreneurship and minimize the likelihood of regrets 

    • How to leverage your 9-to-5 now and add value to your employer before you make the leap

  • An expanded 30-page workbook with practical exercises to help you put each lesson into practice

  • A done-for-you income clarity spreadsheet to help you map out your income goals

  • Lifetime access to the mini course and any future updates

The course will go live on Saturday, June 15. Right now early enrollment has just opened, and you can grab the course now for $50 off, which is just $47. I wanted to make it a no-brainer and an easy yes for you to take this foundational step and be thoughtful about your entrepreneurial goals. Don’t wait to grab your seat in the course because the price jumps up to $97 on June 15th.

Are you a juggler or a slugger?

Click play to listen to this post below.

Are you a juggler or are you a slugger? 

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I was at Andrew Nguyen's #BYOBRetreat this past weekend (which was fantastic and I will do a recap of that at some point soon in the future). During the conference, I had the absolute pleasure and privilege of listening to a keynote by Dia Simms. 

If you don't know, Dia Simms is the president of Combs Enterprises, the holding company for Sean "Diddy" Combs' entities. Dia is the first ever male or female to hold the role of president in 24 years of the company's existence. She's a boss, a wife and mother of a young daughter. 

During the Q&A, someone asked Dia how she balances it all--home, work, husband, daughter, self? Her response is going instantly became a mindset, a movement and a mantra for me. 

She said, "Look, I'm not a clown. I'm not a juggler. I don't juggle things. It's not what I do. Instead, I approach everything as if I'm at a batting cage. I take every ball that comes my way, and I aim, focus and knock it out of the park. When the next ball comes in, I aim, focus and knock it out of the park. So when I'm with my daughter, I'm with my daughter and I knock it out of the park. When I'm in a meeting, I'm really present in that meeting and I knock it out of the park." 

Such good advice, right? 

It really spoke to me because, especially for those of us who are building businesses while working, raising families, raising ourselves . . . it can be a lot. 

By and large, society has glorified the idea of overworking, doing the most and multitasking--something that many women tend to be naturally good at, for better or worse. 

But, in fact, research shows that single tasking is far more productive and we're able to get more out of the time we have when we're focused, in the moment and truly present. 

So, who's down for practicing this subtle mindset shift? Do you want to be a juggler or a slugger? Let's knock some things out of the park.

Join the conversation in the comments on my Instagram post, and let me know if this resonates with you.


Titilayo Tinubu Ali
Founder, Own Your Expertise®

P.S. Juggling work life and business aspirations? I'm putting finishing touches on a new resource for you. Make sure you’re on my email list, and look out for an announcement in the next few weeks.

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.

Want to get started with consulting but not sure where to start?

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

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.


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

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.


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

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.


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

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.