New Year, New Focus: What to Ask Yourself in 2026—and Who to Actually Take Advice From

As 2026 kicks off, the pressure to hit the ground running is real. You’re probably reviewing goals, revisiting metrics, and maybe even rewriting your strategic plan. We all love a good strategy session, a shiny new planner, or a motivational quote at the top of the new year.

But the entrepreneurs who actually shift their trajectory in January aren’t chasing goals.
They’re interrogating assumptions.

Here’s a powerful (and possibly painful) place to start:

What are the questions I should be asking myself this year? And whose advice is actually worth listening to?

Because let’s be honest: if you’re a business owner, you’re making fast, high-stakes decisions every single day. Taking advice from someone who’s never carried that weight might do more harm than good. 

The biggest trap for business owners won’t be burnout or bad marketing. It’ll be noise – not just from social media and all the ‘experts’, but also those around us (whether they know what they are talking about or not).

Too many inputs, from too many people who’ve never been in the game.

That’s like a quarterback with a 300-pound lineman charging at him… asking a fan eating a hotdog in row 32 what play to run.

If they’ve never been in the game, they can’t understand the pressure of real-time decisions.

If you’ve ever been coached—or tried coaching others—you know the frustration of watching someone ignore advice from experience in favor of opinions from convenience.

A client once said to me, “Well, my sister and mom both think I should do more TikToks instead of speak at events.” 

I asked, “Ok, do you have a following there? Is this subject something you think TikTok users would be interested in and be able to afford?” 

(NOTE: She was selling personal strategy coaching with a starting price of $25K)

It’s easy to have clarity from the cheap seats. It costs nothing to be an expert when you risk nothing.

So what should you do to set yourself up for a great New Year?  Be Strategic About Your Questions and Your Influences

Too many entrepreneurs fall into the trap of listening to “armchair experts” who’ve never launched, scaled, or survived owning a business. Like taking parenting advice from someone who has never been a parent. 

Don’t let someone who’s never built anything tell you how to build yours.

If they haven’t felt the sting of rejection, the thrill of closing a deal, or the stress of staying up at night managing cash flow — they’re not your advisor. They’re a spectator.

So, this year, take advice from those in the arena:

• Entrepreneurs ahead of you
• Coaches with small business battle scars
• Professionals who’ve rolled up their sleeves and built something real

This time of year I take a CEO day and ask myself a few tough questions:  Here are 7 Strategic Thought Provoking topics with Questions to Ask Yourself as 2026 Begins

These are reframed from commonly asked questions I use with clients, but here, you’re turning the mirror on yourself. The goal is clarity, focus, and action.

1. Am I running a business I respect – or just a business I built? Am I playing the game I’m wired to win – or one I feel pressured to imitate?

It’s entirely possible to be successful and misaligned.

You may have product-market fit, but not you-market fit.

Just because someone else is scaling a team, building an empire, or chasing exit multiples doesn’t mean you should be.

Some entrepreneurs are builders. Others are artisans. Others are community creators.
Figure out what you want to build – and optimize for that.

Think about this: Would I buy this company today, as it currently operates?

If not, what would need to change?

2. What have I avoided learning because it would challenge my identity?

Sometimes the next level of growth isn’t about new tactics – it’s about unlearning what made you successful in the first place.

Are you clinging to an old version of yourself because it feels safer than becoming someone new?

Do you need to improve your leadership, or your sales skills? How about implementation of AI for your business – in marketing or process implementations? 

Don’t wait until you’re overwhelmed to skill up!

“In the beginner’s mind there are many possibilities, but in the expert’s there are few.” – Shunryu Suzuki

Think about this: What don’t I know that I’m afraid to learn?

Remember: Learning on purpose beats learning in panic.

3. What are my real strengths – and am I using them strategically?

You might be great at sales, but stuck in operations. Or have a brilliant creative mind but spend your time in admin hell.
Maximize your zone of genius. Then ask: what can I delegate or systematize so I can stay there?

4. Where am I too comfortable – and what growth have I been avoiding? Where am I hiding behind “busy”?

Your comfort zone is costing you opportunities. Whether it’s avoiding networking, delaying a hire, or hesitating to raise prices – comfort kills momentum.

Being busy can feel productive, but it often protects us from making hard decisions.

• It’s easier to answer emails than admit your pricing is too low.
• It’s easier to rework your website than have 10 awkward sales conversations.
• It’s easier to fix your calendar than fix your courage.

Think it through: What strategic decision am I postponing by staying in motion?

What’s one uncomfortable move I can make this month that would shift everything?

5. What does success actually look like for me? What’s a success I’m chasing that’s not actually mine?

If your vision feels heavy instead of energizing, it may be borrowed. Let 2026 be the year you delete goals that were never yours to begin with.

Beyond revenue goals – what are the outcomes that matter? Increased referrals? A stronger brand presence? A more confident team?

• If you’re burning yourself out to hit $1M in revenue, ask: Why that number?
• If you’re expanding your team, ask: Is that growth or just ego?

Make success tangible and time-bound. You’re more likely to achieve what you define clearly.

6. What patterns are repeating – and why haven’t I solved them yet? What problem keeps resurfacing – because I benefit from it in some way?

We all have business pain points that linger. But sometimes, they stay because they serve us in hidden ways.

• Do you say you’re too busy to scale… because if you slow down, you’ll have to face uncertainty?
• Are you “too overwhelmed to hire”… because having control feels safer than building trust?

Growth starts when you stop lying to yourself.

If a challenge keeps resurfacing, it’s not a fluke – it’s a signal. Ask yourself if you’re truly addressing the root issue or just treating symptoms.

7. Who do I need in my corner this year?

Your circle is your strategy. Which peers, mentors, or communities will help you think bigger, move faster, or navigate smarter?

Think about this: Do I have the right people around me – do I have a solid personal board of directors to support my efforts? 

Am I involved in a community that pushes me and also offers recources, advice, support, ideas and feedback – one that is filled with small business owners, independent professionals and entrepreneurs?

This now ventures into another often asked question – When to Spend Money: Investment vs. Expense

Think of your resources like a chessboard. You don’t throw your pieces around—you move them with intention.

Not every investment in your business is smart. But some decisions pay you back in time, energy, and momentum. 

Here’s when it makes strategic sense to invest:

A Virtual Assistant (VA):

Hire when you’re:

• Spending hours on low-value tasks (email, scheduling, admin)
• Losing time on things that aren’t in your “zone of genius”
• Delaying customer responses or missing follow-ups
• Tasks are falling through the cracks, or you’re the bottleneck
• Your creativity is compromised by admin

Insight: Hiring a VA isn’t about delegation. It’s about preserving your strategic bandwidth.

ROI: More time to grow, less time in the weeds.

A Business Coach:

Invest when you:

• Feel stuck in growth or leadership decisions
• Need clarity, accountability, and strategy
• Want to learn from someone who’s been there and done that
• You’re facing decisions with long-term consequences (team, pricing, positioning)
• You’re operating in a vacuum and can’t see your own blind spots

Insight: A great coach doesn’t just help you do more – they help you become more.
They sharpen your thinking. They hold your vision when you feel unsure. They see the game you’re trying to win, and they help you play it with integrity.

ROI: Better decisions, faster growth, stronger confidence.
And remember: a good coach won’t give you answers—they’ll help you ask better questions.

A Program or Community:

Join when you:

• Need new ideas, tools, and connections
• Crave accountability and peer feedback
• Feel isolated and want to level up through association
• You need to normalize thinking bigger
• You’ve outgrown your current circle of influence

Insight: If you’re always the smartest or most driven person in the room, you’re in the wrong room

ROI: A stronger network, proven frameworks, and insight from others’ wins and failures.

Alright – SO – how do you get this all together?  My suggestion…do a CEO DAY – take 6-8 hours by yourself – check out = and think.  

IF you just can’t to that – here are the action steps for the First 30 Days of 2026:

1. Audit your circle. Who are you listening to? Whose feedback do you trust? Who do you need to stop listening to?
2. Block 90 minutes this week for CEO-level reflection. Use the 7 questions above as your thinking prompts.
3. Pick one investment area (VA, coach, or community) and explore options. Choose based on your biggest constraint.
4. Recommit to your mission and vision. Recenter your “why” before you continue to build your “how.”

It comes down to this: To really grow and uplevel in 2026 you need to…Ask Better Questions. Seek Aligned Advice.

2026 shouldn’t just be about hustle. It’s about alignment, clarity, and connection. The quality of your outcomes will be a reflection of the quality of your questions and the wisdom of the people you allow to influence your journey.

So this year, trust your instincts – but back them up with experience-based guidance.

Don’t ask the fan eating nachos what play to call or offense to run. Ask the player who’s taken the hits and still shows up every Sunday.